DD297637A5 - Verfahren zur kreuzkopplung mit metallischem palladium-katalysators - Google Patents

Verfahren zur kreuzkopplung mit metallischem palladium-katalysators Download PDF

Info

Publication number: DD297637A5
Authority: DD; German Democratic Republic
Prior art keywords: halogen; compounds; formula; radical; independently
Prior art date: 1989-09-14

Application number

DD90343980A

Other languages

German (de)

English (en)

Inventor

Eike Poetsch

Volker Meyer

Klaus-Peter Stahl

Original Assignee

Merck Patent Gmbh,De

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1989-09-14

Filing date

1990-09-12

Publication date

1992-01-16

1990-09-12 Application filed by Merck Patent Gmbh,De filed Critical Merck Patent Gmbh,De

1992-01-16 Publication of DD297637A5 publication Critical patent/DD297637A5/de

Links

KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 title claims abstract description 48
239000003054 catalyst Substances 0.000 title claims abstract description 11
238000000034 method Methods 0.000 title claims description 20
238000006880 cross-coupling reaction Methods 0.000 title claims description 5
150000001875 compounds Chemical class 0.000 claims abstract description 32
125000000217 alkyl group Chemical group 0.000 claims abstract description 12
150000002902 organometallic compounds Chemical class 0.000 claims abstract description 12
229910052736 halogen Inorganic materials 0.000 claims abstract description 11
229910052763 palladium Inorganic materials 0.000 claims abstract description 11
150000003254 radicals Chemical group 0.000 claims abstract description 10
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
150000002367 halogens Chemical class 0.000 claims abstract description 8
229910052723 transition metal Inorganic materials 0.000 claims abstract description 8
150000003624 transition metals Chemical class 0.000 claims abstract description 8
238000006555 catalytic reaction Methods 0.000 claims abstract description 5
229910052708 sodium Inorganic materials 0.000 claims abstract description 4
HPYIUKIBUJFXII-UHFFFAOYSA-N Cyclopentadienyl radical Chemical compound [CH]1C=CC=C1 HPYIUKIBUJFXII-UHFFFAOYSA-N 0.000 claims abstract description 3
125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
125000005843 halogen group Chemical group 0.000 claims abstract description 3
229910052700 potassium Inorganic materials 0.000 claims abstract description 3
-1 alkenyl radical Chemical class 0.000 claims description 18
229910052744 lithium Inorganic materials 0.000 claims description 9
125000004093 cyano group Chemical group *C#N 0.000 claims description 7
150000002366 halogen compounds Chemical class 0.000 claims description 5
239000000463 material Substances 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
125000001188 haloalkyl group Chemical group 0.000 claims description 2
229910052751 metal Inorganic materials 0.000 abstract description 17
239000002184 metal Substances 0.000 abstract description 17
238000010168 coupling process Methods 0.000 abstract description 15
238000005859 coupling reaction Methods 0.000 abstract description 15
230000008878 coupling Effects 0.000 abstract description 14
NGWQAIWPRVFOPE-UHFFFAOYSA-N 2-pyridin-2-ylpyridine;quinoxalino[2,3-f][1,10]phenanthroline;ruthenium Chemical compound [Ru].N1=CC=CC=C1C1=CC=CC=N1.N1=CC=CC=C1C1=CC=CC=N1.C1=CC=C2C3=NC4=CC=CC=C4N=C3C3=CC=CN=C3C2=N1 NGWQAIWPRVFOPE-UHFFFAOYSA-N 0.000 abstract 1
101100096112 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) snx-3 gene Proteins 0.000 abstract 1
239000012876 carrier material Substances 0.000 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
238000002360 preparation method Methods 0.000 description 11
238000010626 work up procedure Methods 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 10
239000000460 chlorine Substances 0.000 description 10
QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 8
229910052801 chlorine Inorganic materials 0.000 description 7
238000011097 chromatography purification Methods 0.000 description 7
239000000203 mixture Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 6
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
229910052794 bromium Inorganic materials 0.000 description 6
125000001190 organyl group Chemical group 0.000 description 6
239000011734 sodium Substances 0.000 description 6
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
125000003118 aryl group Chemical group 0.000 description 5
239000011777 magnesium Substances 0.000 description 5
229910052749 magnesium Inorganic materials 0.000 description 5
150000002736 metal compounds Chemical class 0.000 description 5
239000007858 starting material Substances 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
125000004429 atom Chemical group 0.000 description 4
229910052731 fluorine Inorganic materials 0.000 description 4
150000004820 halides Chemical class 0.000 description 4
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
229940102001 zinc bromide Drugs 0.000 description 4
KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
150000001649 bromium compounds Chemical class 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
150000001805 chlorine compounds Chemical class 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
SEAOBYFQWJFORM-UHFFFAOYSA-N 1-bromo-4-(trifluoromethoxy)benzene Chemical compound FC(F)(F)OC1=CC=C(Br)C=C1 SEAOBYFQWJFORM-UHFFFAOYSA-N 0.000 description 2
INMMVHOKQLWAQU-UHFFFAOYSA-N 1-phenyl-2-(trifluoromethoxy)benzene Chemical group FC(F)(F)OC1=CC=CC=C1C1=CC=CC=C1 INMMVHOKQLWAQU-UHFFFAOYSA-N 0.000 description 2
HGXWRDPQFZKOLZ-UHFFFAOYSA-N 4-bromo-2-fluorobenzonitrile Chemical compound FC1=CC(Br)=CC=C1C#N HGXWRDPQFZKOLZ-UHFFFAOYSA-N 0.000 description 2
HQSCPPCMBMFJJN-UHFFFAOYSA-N 4-bromobenzonitrile Chemical compound BrC1=CC=C(C#N)C=C1 HQSCPPCMBMFJJN-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 2
238000005577 Kumada cross-coupling reaction Methods 0.000 description 2
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
238000006411 Negishi coupling reaction Methods 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
150000004703 alkoxides Chemical class 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
150000001503 aryl iodides Chemical class 0.000 description 2
YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
INLLPKCGLOXCIV-UHFFFAOYSA-N bromoethene Chemical group BrC=C INLLPKCGLOXCIV-UHFFFAOYSA-N 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
150000002148 esters Chemical group 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
150000004694 iodide salts Chemical class 0.000 description 2
SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 2
239000003446 ligand Substances 0.000 description 2
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
150000002739 metals Chemical class 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
125000002524 organometallic group Chemical group 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
239000007787 solid Substances 0.000 description 2
230000000707 stereoselective effect Effects 0.000 description 2
235000021286 stilbenes Nutrition 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000010936 titanium Substances 0.000 description 2
230000007704 transition Effects 0.000 description 2
WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 2
NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 2
YHUUTZBHAMAEGJ-UHFFFAOYSA-N (4-cyano-3-fluorophenyl) trifluoromethanesulfonate Chemical compound FC1=CC(OS(=O)(=O)C(F)(F)F)=CC=C1C#N YHUUTZBHAMAEGJ-UHFFFAOYSA-N 0.000 description 1
WLCGYIWOKVWFLB-UHFFFAOYSA-N (4-propylphenyl)boronic acid Chemical compound CCCC1=CC=C(B(O)O)C=C1 WLCGYIWOKVWFLB-UHFFFAOYSA-N 0.000 description 1
YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
QUWHOIKFJBTGHZ-UHFFFAOYSA-N 1-bromo-4-(4-pentylcyclohexyl)benzene Chemical compound C1CC(CCCCC)CCC1C1=CC=C(Br)C=C1 QUWHOIKFJBTGHZ-UHFFFAOYSA-N 0.000 description 1
KUZODCHMJPTOPJ-UHFFFAOYSA-N 1-bromo-4-(4-pentylcyclohexyl)cyclohexane Chemical compound C1CC(CCCCC)CCC1C1CCC(Br)CC1 KUZODCHMJPTOPJ-UHFFFAOYSA-N 0.000 description 1
UCCUXODGPMAHRL-UHFFFAOYSA-N 1-bromo-4-iodobenzene Chemical compound BrC1=CC=C(I)C=C1 UCCUXODGPMAHRL-UHFFFAOYSA-N 0.000 description 1
NUPWGLKBGVNSJX-UHFFFAOYSA-N 1-bromo-4-propylbenzene Chemical compound CCCC1=CC=C(Br)C=C1 NUPWGLKBGVNSJX-UHFFFAOYSA-N 0.000 description 1
QPKFVRWIISEVCW-UHFFFAOYSA-N 1-butane boronic acid Chemical compound CCCCB(O)O QPKFVRWIISEVCW-UHFFFAOYSA-N 0.000 description 1
125000005916 2-methylpentyl group Chemical group 0.000 description 1
XMZQWZJMTBCUFT-UHFFFAOYSA-N 3-bromopropylbenzene Chemical compound BrCCCC1=CC=CC=C1 XMZQWZJMTBCUFT-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
RDYVHMTXANAKND-MYPZOXIJSA-N C(CC)[C@@H]1CC[C@H](CC1)C1(CC=C(C=C1)C1=CC=CC=C1)Br Chemical group C(CC)[C@@H]1CC[C@H](CC1)C1(CC=C(C=C1)C1=CC=CC=C1)Br RDYVHMTXANAKND-MYPZOXIJSA-N 0.000 description 1
CSYUEMFRUKEAQA-UHFFFAOYSA-N CC1=NC=C(C(C1Br)(C#N)C)OC Chemical compound CC1=NC=C(C(C1Br)(C#N)C)OC CSYUEMFRUKEAQA-UHFFFAOYSA-N 0.000 description 1
ZJTRAHOHHBGWOO-QAQDUYKDSA-N CCCCCCC[C@H]1CC[C@@H](CC1)c1ccc(C#N)c(F)c1 Chemical compound CCCCCCC[C@H]1CC[C@@H](CC1)c1ccc(C#N)c(F)c1 ZJTRAHOHHBGWOO-QAQDUYKDSA-N 0.000 description 1
241000251730 Chondrichthyes Species 0.000 description 1
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
239000007818 Grignard reagent Substances 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
YMOONIIMQBGTDU-VOTSOKGWSA-N [(e)-2-bromoethenyl]benzene Chemical compound Br\C=C\C1=CC=CC=C1 YMOONIIMQBGTDU-VOTSOKGWSA-N 0.000 description 1
QRZCEXCQSFQDMG-UHFFFAOYSA-N [4-(4-pentylphenyl)phenyl]boronic acid Chemical compound C1=CC(CCCCC)=CC=C1C1=CC=C(B(O)O)C=C1 QRZCEXCQSFQDMG-UHFFFAOYSA-N 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
150000001252 acrylic acid derivatives Chemical class 0.000 description 1
150000007824 aliphatic compounds Chemical class 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
150000001499 aryl bromides Chemical class 0.000 description 1
150000001540 azides Chemical class 0.000 description 1
238000007068 beta-elimination reaction Methods 0.000 description 1
150000001639 boron compounds Chemical class 0.000 description 1
230000031709 bromination Effects 0.000 description 1
238000005893 bromination reaction Methods 0.000 description 1
150000004768 bromobenzenes Chemical class 0.000 description 1
KNMKGOLZNOKQGK-UHFFFAOYSA-N bromoborane Chemical compound BrB KNMKGOLZNOKQGK-UHFFFAOYSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
JHAYEQICABJSTP-UHFFFAOYSA-N decoquinate Chemical group N1C=C(C(=O)OCC)C(=O)C2=C1C=C(OCC)C(OCCCCCCCCCC)=C2 JHAYEQICABJSTP-UHFFFAOYSA-N 0.000 description 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000005595 deprotonation Effects 0.000 description 1
238000010537 deprotonation reaction Methods 0.000 description 1
239000012954 diazonium Substances 0.000 description 1
150000001989 diazonium salts Chemical class 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical group [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
HSUGRBWQSSZJOP-RTWAWAEBSA-N diltiazem Chemical compound C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CCN(C)C)C2=CC=CC=C2S1 HSUGRBWQSSZJOP-RTWAWAEBSA-N 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
150000004795 grignard reagents Chemical class 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001072 heteroaryl group Chemical group 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
WMIYKQLTONQJES-UHFFFAOYSA-N hexafluoroethane Chemical compound FC(F)(F)C(F)(F)F WMIYKQLTONQJES-UHFFFAOYSA-N 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
239000011630 iodine Substances 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000007788 liquid Substances 0.000 description 1
IHTNAUBJNDBCCT-UHFFFAOYSA-N lithium 2,3-ditert-butyl-1H-naphthalen-1-ide Chemical compound C(C)(C)(C)C=1C(=[C-]C2=CC=CC=C2C=1)C(C)(C)C.[Li+] IHTNAUBJNDBCCT-UHFFFAOYSA-N 0.000 description 1
YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
BNHFWQQYLUPDOG-UHFFFAOYSA-N lithium;1,2,2,3-tetramethylpiperidine Chemical compound [Li].CC1CCCN(C)C1(C)C BNHFWQQYLUPDOG-UHFFFAOYSA-N 0.000 description 1
GQNMAZUQZDEAFI-UHFFFAOYSA-N lithium;1h-naphthalen-1-ide Chemical compound [Li+].[C-]1=CC=CC2=CC=CC=C21 GQNMAZUQZDEAFI-UHFFFAOYSA-N 0.000 description 1
UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
229910001507 metal halide Inorganic materials 0.000 description 1
150000005309 metal halides Chemical class 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
239000003863 metallic catalyst Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000002825 nitriles Chemical group 0.000 description 1
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000002900 organolithium compounds Chemical class 0.000 description 1
238000006464 oxidative addition reaction Methods 0.000 description 1
ZOUWOGOTHLRRLS-UHFFFAOYSA-N palladium;phosphane Chemical compound P.[Pd] ZOUWOGOTHLRRLS-UHFFFAOYSA-N 0.000 description 1
RURREWSZSUQSNB-UHFFFAOYSA-N pent-4-enylbenzene Chemical compound C=CCCCC1=CC=CC=C1 RURREWSZSUQSNB-UHFFFAOYSA-N 0.000 description 1
125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229910000073 phosphorus hydride Inorganic materials 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000746 purification Methods 0.000 description 1
QLULGIRFKAWHOJ-UHFFFAOYSA-N pyridin-4-ylboronic acid Chemical compound OB(O)C1=CC=NC=C1 QLULGIRFKAWHOJ-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
WBQTXTBONIWRGK-UHFFFAOYSA-N sodium;propan-2-olate Chemical compound [Na+].CC(C)[O-] WBQTXTBONIWRGK-UHFFFAOYSA-N 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
150000001629 stilbenes Chemical class 0.000 description 1
238000003756 stirring Methods 0.000 description 1
150000003440 styrenes Chemical class 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
150000003609 titanium compounds Chemical class 0.000 description 1
238000006478 transmetalation reaction Methods 0.000 description 1
125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000002604 ultrasonography Methods 0.000 description 1
125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
238000010792 warming Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000002351 wastewater Substances 0.000 description 1
150000003751 zinc Chemical class 0.000 description 1
150000003755 zirconium compounds Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
- C07C15/42—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals monocyclic
- C07C15/44—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals monocyclic the hydrocarbon substituent containing a carbon-to-carbon double bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/50—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/21—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing rings other than six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/782—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic
- C07C49/792—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic containing rings other than six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
- C07C49/813—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen polycyclic
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Pyridine Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Catalysts (AREA)

DD90343980A 1989-09-14 1990-09-12 Verfahren zur kreuzkopplung mit metallischem palladium-katalysators DD297637A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE3930663A DE3930663C1 (en)	1989-09-14	1989-09-14	Cross-coupling metal organic cpds. and e.g. halogen cpds. - includes using transition metal-palladium catalyst and opt. metal alcoholate

Publications (1)

Publication Number	Publication Date
DD297637A5 true DD297637A5 (de)	1992-01-16

Family

ID=6389381

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD90343980A DD297637A5 (de)	1989-09-14	1990-09-12	Verfahren zur kreuzkopplung mit metallischem palladium-katalysators

Country Status (3)

Country	Link
JP (1)	JP2907979B2 (ja)
DD (1)	DD297637A5 (ja)
DE (1)	DE3930663C1 (ja)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5382672A (en) *	1992-10-12	1995-01-17	Synthelabo	Preparation of derivatives of benzeneborinic acid

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH683522A5 (de) *	1992-03-13	1994-03-31	Hoffmann La Roche	Verfahren zur Herstellung von Diarylen.
DE4236103A1 (de) *	1992-10-26	1994-04-28	Hoechst Ag	Verfahren zur Kreuzkupplung von aromatischen Boronsäuren mit aromatischen Halogenverbindungen oder Perfluoralkylsulfonaten
GB2277928A (en) *	1993-05-12	1994-11-16	Merck Patent Gmbh	Cyclohexyl- and cyclohexylethyl- fluorobiphenyls and liquid-crystalline compositions thereof
DE4414499A1 (de) *	1994-04-26	1995-11-02	Hoechst Ag	Verfahren zur Kreuzkupplung von aromatischen Borverbindungen mit aromatischen Halogenverbindungen oder Perfluoralkylsulfonaten
DE4415049A1 (de)	1994-04-29	1995-11-02	Hoechst Schering Agrevo Gmbh	Acylierte Aminophenylsulfonylharnstoffe, Verfahren zu deren Herstellung und Verwendung als Herbizide und Wachstumsregulatoren
DE4423098A1 (de)	1994-07-01	1996-01-04	Hoechst Ag	Verwendung von Pyrimidingruppen enthaltenden konjugierten Verbindungen als Elektrolumineszenzmaterialien
JP3780547B2 (ja) *	1995-09-13	2006-05-31	大日本インキ化学工業株式会社	ビシクロヘキサン誘導体
DE19607135C1 (de) *	1996-02-26	1997-04-24	Great Lakes Chem Konstanz Gmbh	Verfahren zur Herstellung von unsymmetrisch substituierten Biphenylen
JP4507294B2 (ja) *	1999-05-27	2010-07-21	チッソ株式会社	ビアリール誘導体の製造方法
US6858592B2 (en)	2001-06-29	2005-02-22	Genzyme Corporation	Aryl boronic acids for treating obesity
US7041280B2 (en)	2001-06-29	2006-05-09	Genzyme Corporation	Aryl boronate functionalized polymers for treating obesity
CA2676802A1 (en) *	2007-01-29	2008-08-07	Wako Pure Chemical Industries, Ltd.	Reagent for organic synthesis reaction containing organic triol borate salt
CN101182310B (zh) *	2007-12-06	2010-04-14	华东理工大学	联苯基取代的嘧啶类化合物的制备方法
CN106316881B (zh) *	2016-08-23	2018-09-11	中节能万润股份有限公司	一种环己基含氟苯腈衍生物液晶单体的制备方法

1989
- 1989-09-14 DE DE3930663A patent/DE3930663C1/de not_active Expired - Fee Related
1990
- 1990-09-12 DD DD90343980A patent/DD297637A5/de not_active IP Right Cessation
- 1990-09-14 JP JP2242851A patent/JP2907979B2/ja not_active Expired - Fee Related

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5382672A (en) *	1992-10-12	1995-01-17	Synthelabo	Preparation of derivatives of benzeneborinic acid

Also Published As

Publication number	Publication date
JPH03123736A (ja)	1991-05-27
DE3930663C1 (en)	1990-11-15
JP2907979B2 (ja)	1999-06-21

Legal Events

Date	Code	Title	Description
1997-06-19	ENJ	Ceased due to non-payment of renewal fee
2001-04-12	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
EP0665825B1 (de)	1997-01-15	Verfahren zur kreuzkupplung von aromatischen boronsäuren mit aromatischen halogenverbindungen oder perfluoralkylsulfonaten
EP0694530B1 (de)	2000-08-23	Verfahren zur Kreuzkupplung von aromatischen Borverbindungen mit aromatischen Halogenverbindungen oder Perfluoralkylsulfonaten
DE3246440C2 (de)	1995-04-20	Acetylene
DD297637A5 (de)	1992-01-16	Verfahren zur kreuzkopplung mit metallischem palladium-katalysators
EP0216880B1 (de)	1988-11-02	Cyclohexanderivate
EP0215120A1 (de)	1987-03-25	Cyclohexanderivate.
DE3515373A1 (de)	1986-11-06	Stickstoffhaltige heterocyclen
CH683522A5 (de)	1994-03-31	Verfahren zur Herstellung von Diarylen.
EP0679619B1 (de)	2001-10-17	Verfahren zur Kreuzkupplung von aromatischen Borverbindungen mit aromatischen Halogenverbindungen oder Perfluoralkylsulfonaten
EP0338054B1 (de)	1992-12-30	Kreuzkopplung von titanorganylen
DD284022A5 (de)	1990-10-31	Verfahren zur herstellung von staebchenfoermigen verbindungen der formel i
EP0282542B1 (de)	1994-05-18	Verfahren zur herstellung von alkylen- bzw. ringverknüpften verbindungen
DE4220065A1 (de)	1993-12-23	Verfahren zur Herstellung von Pyrimidin-Derivaten
EP0290570A1 (de)	1988-11-17	Chirale oder achirale ringverbindungen.
EP0283490B1 (de)	1992-01-08	Verfahren zur herstellung von ethanderivaten
EP0709357A1 (de)	1996-05-01	Verfahren zur Kreuzkupplung von aromatischen Halogenverbindungen oder Perfluoralkylsulfonaten mit terminalen Alkinen
EP0261160B1 (de)	1991-03-06	Alicyclische Verbindungen
DE4340490A1 (de)	1994-06-01	Verbessertes Verfahren zur Durchführung einer Kreuzkopplungsreaktion
DE4438586A1 (de)	1996-05-02	Verfahren zur Kreuzkupplung von aromatischen Halogenverbindungen oder Perfluoralkylsulfonaten mit terminalen Alkinen
WO1991006522A2 (de)	1991-05-16	Phenylcyclohexane und flüssigkristallines medium
DE4438877A1 (de)	1996-05-02	Verfahren zur Kreuzkupplung von aromatischen Halogenverbindungen oder Perfluoralkylsulfonaten mit terminalen Alkinen
WO1994010179A1 (de)	1994-05-11	Arylboronsäuren als vorprodukte zur herstellung von komponenten von flüssigkristallmischungen
DE19755509B4 (de)	2006-01-19	Cyclobutanon-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung flüssigkristalliner Verbindungen
DE3608502A1 (de)	1987-09-17	Verfahren zur herstellung von tertiaeren alkoholen mit titanorganischen verbindungen

DD297637A5 - Verfahren zur kreuzkopplung mit metallischem palladium-katalysators - Google Patents

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Applications Claiming Priority (1)

Publications (1)

Family

ID=6389381

Family Applications (1)

Country Status (3)

Cited By (1)

Families Citing this family (14)

Cited By (1)

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