CA2645101C - Ligands pour metaux et processus perfectionnes catalyses par des metaux bases sur ceux-ci - Google Patents

Ligands pour metaux et processus perfectionnes catalyses par des metaux bases sur ceux-ci Download PDF

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Publication number: CA2645101C
Authority: CA; Canada
Prior art keywords: aryl; alkyl; represented; group; ligand
Prior art date: 1998-07-10
Legal status (The legal status 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 status listed.): Expired - Lifetime

Application number

CA2645101A

Other languages

English (en)

Other versions

CA2645101A1 (fr

Inventor

Stephen L. Buchwald

David W. Old

John P. Wolfe

Michael Palcuki

Ken Kamikawa

Andrew Chieffi

Joseph P. Sadighi

Robert A. Singer

Jens Ahman

Malisa Troutman

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Massachusetts Institute of Technology

Original Assignee

Massachusetts Institute of Technology

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.)

1998-07-10

Filing date

1999-07-09

Publication date

2013-04-16

1998-07-10 Priority claimed from US09/113,478 external-priority patent/US6395916B1/en

1999-01-13 Priority claimed from US09/231,315 external-priority patent/US6307087B1/en

1999-01-27 Priority claimed from US09/239,024 external-priority patent/US6867310B1/en

1999-07-09 Application filed by Massachusetts Institute of Technology filed Critical Massachusetts Institute of Technology

1999-07-09 Priority claimed from CA002336691A external-priority patent/CA2336691C/fr

2000-01-20 Publication of CA2645101A1 publication Critical patent/CA2645101A1/fr

2013-04-16 Application granted granted Critical

2013-04-16 Publication of CA2645101C publication Critical patent/CA2645101C/fr

2019-07-09 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 540
239000003446 ligand Substances 0.000 title claims abstract description 340
230000008569 process Effects 0.000 title claims abstract description 131
229910052751 metal Inorganic materials 0.000 title claims description 75
239000002184 metal Substances 0.000 title claims description 69
150000002739 metals Chemical class 0.000 title description 23
238000006243 chemical reaction Methods 0.000 claims abstract description 232
229910052723 transition metal Inorganic materials 0.000 claims abstract description 159
150000003624 transition metals Chemical class 0.000 claims abstract description 159
239000003054 catalyst Substances 0.000 claims abstract description 118
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 259
125000003118 aryl group Chemical group 0.000 claims description 259
125000000217 alkyl group Chemical group 0.000 claims description 172
-1 cyano, nitro, azido, sulfhydryl Chemical group 0.000 claims description 144
125000001072 heteroaryl group Chemical group 0.000 claims description 135
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 130
229910052763 palladium Inorganic materials 0.000 claims description 113
150000001875 compounds Chemical class 0.000 claims description 93
125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 84
125000000623 heterocyclic group Chemical group 0.000 claims description 79
239000012035 limiting reagent Substances 0.000 claims description 68
239000007787 solid Substances 0.000 claims description 65
229910052736 halogen Inorganic materials 0.000 claims description 63
229910019142 PO4 Inorganic materials 0.000 claims description 62
150000002367 halogens Chemical class 0.000 claims description 62
229910052786 argon Inorganic materials 0.000 claims description 60
150000001408 amides Chemical class 0.000 claims description 59
229910052739 hydrogen Inorganic materials 0.000 claims description 57
239000000203 mixture Substances 0.000 claims description 56
LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical group [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 claims description 56
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 54
239000010452 phosphate Substances 0.000 claims description 53
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 52
125000003342 alkenyl group Chemical group 0.000 claims description 52
125000003545 alkoxy group Chemical group 0.000 claims description 52
125000004414 alkyl thio group Chemical group 0.000 claims description 52
229910052757 nitrogen Inorganic materials 0.000 claims description 48
150000004703 alkoxides Chemical class 0.000 claims description 47
125000005842 heteroatom Chemical group 0.000 claims description 46
150000001805 chlorine compounds Chemical group 0.000 claims description 45
239000001257 hydrogen Substances 0.000 claims description 44
238000005576 amination reaction Methods 0.000 claims description 43
229910052717 sulfur Inorganic materials 0.000 claims description 42
238000006254 arylation reaction Methods 0.000 claims description 39
229910052760 oxygen Inorganic materials 0.000 claims description 38
125000001424 substituent group Chemical group 0.000 claims description 38
229910052794 bromium Inorganic materials 0.000 claims description 37
229910052801 chlorine Inorganic materials 0.000 claims description 37
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 36
150000002148 esters Chemical class 0.000 claims description 36
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 35
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 35
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 32
125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 32
150000004820 halides Chemical class 0.000 claims description 31
LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims description 31
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 30
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 30
150000002466 imines Chemical class 0.000 claims description 28
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 28
229910052740 iodine Inorganic materials 0.000 claims description 27
ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 claims description 26
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 26
125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 25
150000001409 amidines Chemical class 0.000 claims description 25
238000005859 coupling reaction Methods 0.000 claims description 25
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 25
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 24
125000003368 amide group Chemical group 0.000 claims description 24
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 24
229920000642 polymer Polymers 0.000 claims description 24
125000004429 atom Chemical group 0.000 claims description 23
125000004432 carbon atom Chemical group C* 0.000 claims description 23
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 21
229910000160 potassium phosphate Inorganic materials 0.000 claims description 21
235000011009 potassium phosphates Nutrition 0.000 claims description 20
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 18
125000003282 alkyl amino group Chemical group 0.000 claims description 18
125000005110 aryl thio group Chemical group 0.000 claims description 18
125000004104 aryloxy group Chemical group 0.000 claims description 18
125000001769 aryl amino group Chemical group 0.000 claims description 17
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 16
125000004093 cyano group Chemical group *C#N 0.000 claims description 16
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
229910052799 carbon Inorganic materials 0.000 claims description 13
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
125000006575 electron-withdrawing group Chemical group 0.000 claims description 11
ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 claims description 10
125000002950 monocyclic group Chemical group 0.000 claims description 10
238000007341 Heck reaction Methods 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
238000006886 vinylation reaction Methods 0.000 claims description 8
125000002252 acyl group Chemical group 0.000 claims description 7
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 7
101100240678 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) NNR2 gene Proteins 0.000 claims description 6
HDCXQTPVTAIPNZ-UHFFFAOYSA-N n-({[4-(aminosulfonyl)phenyl]amino}carbonyl)-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NC1=CC=C(S(N)(=O)=O)C=C1 HDCXQTPVTAIPNZ-UHFFFAOYSA-N 0.000 claims description 6
125000000018 nitroso group Chemical group N(=O)* 0.000 claims description 6
150000003138 primary alcohols Chemical class 0.000 claims description 4
125000004665 trialkylsilyl group Chemical group 0.000 claims description 3
125000005106 triarylsilyl group Chemical group 0.000 claims description 3
229910004749 OS(O)2 Inorganic materials 0.000 claims 36
125000006649 (C2-C20) alkynyl group Chemical group 0.000 claims 10
125000006717 (C3-C10) cycloalkenyl group Chemical group 0.000 claims 7
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 2
239000000758 substrate Substances 0.000 abstract description 34
230000007704 transition Effects 0.000 abstract description 9
238000006555 catalytic reaction Methods 0.000 abstract description 7
230000006872 improvement Effects 0.000 abstract description 4
238000010485 C−C bond formation reaction Methods 0.000 abstract description 2
238000010743 carbon-heteroatom bond forming reactions‎ Methods 0.000 abstract description 2
239000000047 product Substances 0.000 description 113
239000002585 base Substances 0.000 description 102
125000000753 cycloalkyl group Chemical group 0.000 description 94
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 92
125000004404 heteroalkyl group Chemical group 0.000 description 68
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 66
150000001412 amines Chemical class 0.000 description 55
125000003710 aryl alkyl group Chemical group 0.000 description 53
150000001500 aryl chlorides Chemical class 0.000 description 53
239000000460 chlorine Substances 0.000 description 50
125000004475 heteroaralkyl group Chemical group 0.000 description 50
150000002576 ketones Chemical class 0.000 description 49
230000015572 biosynthetic process Effects 0.000 description 46
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
235000021317 phosphate Nutrition 0.000 description 45
238000003786 synthesis reaction Methods 0.000 description 43
MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 38
125000000592 heterocycloalkyl group Chemical group 0.000 description 37
125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 description 32
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 32
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 30
125000000392 cycloalkenyl group Chemical group 0.000 description 30
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 29
101150041968 CDC13 gene Proteins 0.000 description 28
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 28
238000006069 Suzuki reaction reaction Methods 0.000 description 28
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 28
239000011541 reaction mixture Substances 0.000 description 28
150000002431 hydrogen Chemical class 0.000 description 27
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 27
239000011324 bead Substances 0.000 description 26
125000000304 alkynyl group Chemical group 0.000 description 24
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 23
150000001499 aryl bromides Chemical class 0.000 description 23
239000010410 layer Substances 0.000 description 22
ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 21
239000002904 solvent Substances 0.000 description 21
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 20
XJHCXCQVJFPJIK-UHFFFAOYSA-M cesium fluoride Substances [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 20
239000003153 chemical reaction reagent Substances 0.000 description 20
239000013058 crude material Substances 0.000 description 20
239000000376 reactant Substances 0.000 description 19
NPDACUSDTOMAMK-UHFFFAOYSA-N 4-Chlorotoluene Chemical compound CC1=CC=C(Cl)C=C1 NPDACUSDTOMAMK-UHFFFAOYSA-N 0.000 description 18
238000005481 NMR spectroscopy Methods 0.000 description 18
238000003818 flash chromatography Methods 0.000 description 18
238000004817 gas chromatography Methods 0.000 description 18
229960001866 silicon dioxide Drugs 0.000 description 18
229910000404 tripotassium phosphate Inorganic materials 0.000 description 18
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 17
150000001502 aryl halides Chemical class 0.000 description 17
230000003197 catalytic effect Effects 0.000 description 17
239000000741 silica gel Substances 0.000 description 17
229910002027 silica gel Inorganic materials 0.000 description 17
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 16
239000004809 Teflon Substances 0.000 description 16
229920006362 Teflon® Polymers 0.000 description 16
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 15
239000012298 atmosphere Substances 0.000 description 15
229910000073 phosphorus hydride Inorganic materials 0.000 description 15
239000000243 solution Substances 0.000 description 15
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 14
150000001299 aldehydes Chemical class 0.000 description 14
230000008878 coupling Effects 0.000 description 14
238000010168 coupling process Methods 0.000 description 14
229920001971 elastomer Polymers 0.000 description 14
ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 14
230000008093 supporting effect Effects 0.000 description 14
235000019798 tripotassium phosphate Nutrition 0.000 description 14
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 13
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 13
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 13
HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 13
239000000126 substance Substances 0.000 description 13
125000003107 substituted aryl group Chemical group 0.000 description 13
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 12
125000005647 linker group Chemical group 0.000 description 12
229910052759 nickel Inorganic materials 0.000 description 12
239000007858 starting material Substances 0.000 description 11
238000006467 substitution reaction Methods 0.000 description 11
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 10
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 10
239000003921 oil Substances 0.000 description 10
235000019198 oils Nutrition 0.000 description 10
239000012044 organic layer Substances 0.000 description 10
238000006464 oxidative addition reaction Methods 0.000 description 10
238000002360 preparation method Methods 0.000 description 10
238000003756 stirring Methods 0.000 description 10
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 10
230000009466 transformation Effects 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
150000001491 aromatic compounds Chemical class 0.000 description 9
MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 9
150000004649 carbonic acid derivatives Chemical class 0.000 description 9
239000012230 colorless oil Substances 0.000 description 9
238000006880 cross-coupling reaction Methods 0.000 description 9
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 9
150000002222 fluorine compounds Chemical class 0.000 description 9
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
150000003013 phosphoric acid derivatives Chemical class 0.000 description 9
108090000765 processed proteins & peptides Proteins 0.000 description 9
125000006239 protecting group Chemical group 0.000 description 9
WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 9
238000012360 testing method Methods 0.000 description 9
238000005160 1H NMR spectroscopy Methods 0.000 description 8
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 8
125000003277 amino group Chemical group 0.000 description 8
150000004982 aromatic amines Chemical class 0.000 description 8
125000004122 cyclic group Chemical group 0.000 description 8
JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 8
239000000284 extract Substances 0.000 description 8
238000005755 formation reaction Methods 0.000 description 8
239000011159 matrix material Substances 0.000 description 8
239000001301 oxygen Substances 0.000 description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 8
150000001241 acetals Chemical class 0.000 description 7
XQJHRCVXRAJIDY-UHFFFAOYSA-N aminophosphine Chemical class PN XQJHRCVXRAJIDY-UHFFFAOYSA-N 0.000 description 7
238000013459 approach Methods 0.000 description 7
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
239000004305 biphenyl Substances 0.000 description 7
235000010290 biphenyl Nutrition 0.000 description 7
FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 7
239000007795 chemical reaction product Substances 0.000 description 7
VPLLTGLLUHLIHA-UHFFFAOYSA-N dicyclohexyl(phenyl)phosphane Chemical compound C1CCCCC1P(C=1C=CC=CC=1)C1CCCCC1 VPLLTGLLUHLIHA-UHFFFAOYSA-N 0.000 description 7
238000003379 elimination reaction Methods 0.000 description 7
150000003949 imides Chemical class 0.000 description 7
239000000463 material Substances 0.000 description 7
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
230000035484 reaction time Effects 0.000 description 7
239000011593 sulfur Substances 0.000 description 7
LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 6
HYTRYEXINDDXJK-UHFFFAOYSA-N Ethyl isopropyl ketone Chemical compound CCC(=O)C(C)C HYTRYEXINDDXJK-UHFFFAOYSA-N 0.000 description 6
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 6
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
239000008346 aqueous phase Substances 0.000 description 6
238000003556 assay Methods 0.000 description 6
150000001540 azides Chemical class 0.000 description 6
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150000004678 hydrides Chemical class 0.000 description 1
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238000002823 phage display Methods 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
150000008300 phosphoramidites Chemical class 0.000 description 1
238000001394 phosphorus-31 nuclear magnetic resonance spectrum Methods 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
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239000011736 potassium bicarbonate Substances 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
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LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000002243 precursor Substances 0.000 description 1
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150000004040 pyrrolidinones Chemical class 0.000 description 1
238000011002 quantification Methods 0.000 description 1
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229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
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239000000523 sample Substances 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
150000003346 selenoethers Chemical class 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
238000012163 sequencing technique Methods 0.000 description 1
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
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239000010935 stainless steel Substances 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
150000008053 sultones Chemical class 0.000 description 1
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
229910021515 thallium hydroxide Inorganic materials 0.000 description 1
QGYXCSSUHCHXHB-UHFFFAOYSA-M thallium(i) hydroxide Chemical compound [OH-].[Tl+] QGYXCSSUHCHXHB-UHFFFAOYSA-M 0.000 description 1
DUYAAUVXQSMXQP-UHFFFAOYSA-M thioacetate Chemical compound CC([S-])=O DUYAAUVXQSMXQP-UHFFFAOYSA-M 0.000 description 1
150000003568 thioethers Chemical group 0.000 description 1
QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 1
RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
238000007832 transition metal-catalyzed coupling reaction Methods 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
229940062627 tribasic potassium phosphate Drugs 0.000 description 1
XTTGYFREQJCEML-UHFFFAOYSA-N tributyl phosphite Chemical compound CCCCOP(OCCCC)OCCCC XTTGYFREQJCEML-UHFFFAOYSA-N 0.000 description 1
TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
FICPQAZLPKLOLH-UHFFFAOYSA-N tricyclohexyl phosphite Chemical compound C1CCCCC1OP(OC1CCCCC1)OC1CCCCC1 FICPQAZLPKLOLH-UHFFFAOYSA-N 0.000 description 1
BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
150000008648 triflates Chemical class 0.000 description 1
UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
SJHCUXCOGGKFAI-UHFFFAOYSA-N tripropan-2-yl phosphite Chemical compound CC(C)OP(OC(C)C)OC(C)C SJHCUXCOGGKFAI-UHFFFAOYSA-N 0.000 description 1
QOPBTFMUVTXWFF-UHFFFAOYSA-N tripropyl phosphite Chemical compound CCCOP(OCCC)OCCC QOPBTFMUVTXWFF-UHFFFAOYSA-N 0.000 description 1
KCTAHLRCZMOTKM-UHFFFAOYSA-N tripropylphosphane Chemical compound CCCP(CCC)CCC KCTAHLRCZMOTKM-UHFFFAOYSA-N 0.000 description 1
230000007306 turnover Effects 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

CA2645101A 1998-07-10 1999-07-09 Ligands pour metaux et processus perfectionnes catalyses par des metaux bases sur ceux-ci Expired - Lifetime CA2645101C (fr)

Applications Claiming Priority (9)

Application Number	Priority Date	Filing Date	Title
US09/113,478 US6395916B1 (en)	1998-07-10	1998-07-10	Ligands for metals and improved metal-catalyzed processes based thereon
US09/113,478		1998-07-10
US19685598A	1998-11-20	1998-11-20
US09/196,855		1998-11-20
US09/231,315 US6307087B1 (en)	1998-07-10	1999-01-13	Ligands for metals and improved metal-catalyzed processes based thereon
US09/231,315		1999-01-13
US09/239,024		1999-01-27
US09/239,024 US6867310B1 (en)	1997-11-20	1999-01-27	Arylation and vinylation of activated carbons
CA002336691A CA2336691C (fr)	1998-07-10	1999-07-09	Ligands pour metaux et processus perfectionnes catalyses par des metaux bases sur ceux-ci

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CN114669333B (zh) *	2022-04-25	2023-06-23	中山大学	一种催化α-季碳醛脱羰氢化的催化剂体系和催化方法
CN116258094B (zh) *	2023-02-02	2024-02-06	中国石油大学(北京)	基于氧化动力学参数的油藏注空气驱可行性判别方法

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EP1097158B1 (fr)	2006-01-25	Ligands pour metaux et procedes de catalyse par metaux
US6307087B1 (en)	2001-10-23	Ligands for metals and improved metal-catalyzed processes based thereon
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US6395916B1 (en)	2002-05-28	Ligands for metals and improved metal-catalyzed processes based thereon
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CN100548948C (zh)	2009-10-14	金属配体以及以此为基础的改良的金属催化方法
JP5758844B2 (ja)	2015-08-05	金属用のリガンドおよびそれらに基づいて改善された金属触媒法
CA2645101C (fr)	2013-04-16	Ligands pour metaux et processus perfectionnes catalyses par des metaux bases sur ceux-ci