DK2880013T3 - Fremgangsmåde til fremstilling af substituerede biphenyler ved hjælp af c-h-aktivering - Google Patents

Fremgangsmåde til fremstilling af substituerede biphenyler ved hjælp af c-h-aktivering Download PDF

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Publication number
DK2880013T3
DK2880013T3 DK13742231.7T DK13742231T DK2880013T3 DK 2880013 T3 DK2880013 T3 DK 2880013T3 DK 13742231 T DK13742231 T DK 13742231T DK 2880013 T3 DK2880013 T3 DK 2880013T3
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formula
iva
groups
process according
methyl
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DK13742231.7T
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Lars Rodefeld
Frank Volz
Matthias Riedrich
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Bayer Cropscience Ag
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0201—Oxygen-containing compounds
    • B01J31/0202—Alcohols or phenols
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208—Oxygen, e.g. acetylacetonates
    • B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
    • B01J31/223—At least two oxygen atoms present in one at least bidentate or bridging ligand
    • B01J31/2239—Bridging ligands, e.g. OAc in Cr2(OAc)4, Pt4(OAc)8 or dicarboxylate ligands
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2282—Unsaturated compounds used as ligands
    • B01J31/2295—Cyclic compounds, e.g. cyclopentadienyls
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
    • C07C211/45—Monoamines
    • C07C211/48—N-alkylated amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
    • C07C233/15—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
    • B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
    • B01J2231/4205—C-C cross-coupling, e.g. metal catalyzed or Friedel-Crafts type
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/10—Complexes comprising metals of Group I (IA or IB) as the central metal
    • B01J2531/16—Copper
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/822—Rhodium

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Inorganic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)
  • Pyridine Compounds (AREA)

Claims (14)

  1. 1. Fremgangsmåde til fremstilling af substituerede biphenyler med formel (III)
    (III) idet X1 og X2 uafhængigt af hinanden er udvalgt af fluor og chlor; n er udvalgt af 0 og 1; m er udvalgt af 1, 2 og 3; R1 er udvalgt af -NHR2, -NR3-CO-R2 og -N=CR4R5; R2 - R5 er udvalgt af hydrogen, lineære eller forgrenede Ci-6~ alkylgrupper, -CH2-CO-CH3, pyrazolylgrupper med formel (IVa) og pyridylgrupper med formel (IVb)
    idet den med # markerede binding i formlerne (IVa) og (IVb), såfremt RI står for -NR3-CO-R2, hver gang er forbundet med carbonylgruppen. R6 og R7 er udvalgt af hydrogen, halogen, en lineær eller forgrenet Ci-6-alkylgruppe og en Ci-6-haloalkylgruppe med 1 til 6 halogenatomer; hn^ip af omsætning af arener med formel (I) (I) idet R1, X1 og n svarer til de ovennævnte definitioner, medarener med formel (II)
    (II) idet X2 og m svarer til de ovennævnte definitioner, idet reaktionen gennemføres i nærvær af en overgangsmetalkatalysator, i det mindste et oxidationsmiddel, op til fem additiver og i et opløsningsmiddel.
  2. 2. Fremgangsmåde ifølge krav 1, idet R1 er -NR3-CO-R2.
  3. 3. Fremgangsmåde ifølge et af kravene 1 eller 2, idet X1 i formel (III) er 5-fluor; n er 1 ; X2 i formel (III) er 3,4-chlor; m er 2 ; R1 er -NH-CO-R2; R2 er udvalgt af methyl, - CH2-CO-CH3 og pyrazolylgrupper med formel (IVa)
    (IVa) idet den med # markerede binding i formel (IVa), såfremt R1 står for -NH-CO-R2, hver gang er forbundet med carbonylgruppen; R6 er difluormethyl, og R7 er hydrogen.
  4. 4. Fremgangsmåde ifølge et af kravene 1 eller 2, idet n er 0; X2 i formel (III) er 3,4,5-fluor; m er 3; R1 er -NH-CO-R2; R2 er udvalgt af methyl, - CH2-CO-CH3 og pyrazolylgrupper med formel (IVa)
    (IVa) idet den med # markerede binding i formel (IVa), såfremt R1 står for -NH-CO-R2, hver gang er forbundet med carbonylgruppen; R6 er difluormethyl, og R7 er hydrogen.
  5. 5. Fremgangsmåde ifølge et af kravene 1 eller 2, idet n er 0; X2 i formel (III) er 4-chlor;
    m er 1 ; R1 er -NH-CO-R2; R2 er udvalgt af gruppen bestående af methyl, - CH2-CO-CH3 og pyridylgrupper med formel (IVb)
    (IVb); idet den med # markerede binding i formel (IVb), såfremt R1 står for -NH-CO-R2, hver gang er forbundet med carbonylgruppen.
  6. 6. Fremgangsmåde ifølge et af kravene 1 til 5, idet arenerne med formel (I) er udvalgt af anilin, 4-fluoranilin, acetanilid, 4-fluoracetanilid, N-phenyl-3-oxobutanamid, N- (4-fluorphenyl)-3-oxobutanamid, N-(propan-2-yliden)anilin, 4-fluor-N-(propan-2-yliden)anilin, N-phenyl-3-(difluormethyl)-1-methyl-lH-pyrazol-4-carboxamid, N-(4-fluorphenyl)-3- (difluormethyl)-l-methyl-lH-pyrazol-4-carboxamid og N-phenyl-2-chlornicotinamid.
  7. 7. Fremgangsmåde ifølge et af kravene 1 til 6, idet arenerne med formel (II) er udvalgt af 1,2-dichlorbenzen, chlorbenzen og 1,2,3-trifluorbenzen.
  8. 8. Fremgangsmåde ifølge et af kravene 1 til 7, idet opløsningsmidlet er udvalgt af 1,2-dichlorbenzen, chlorbenzen, 1,2,3-trifluorbenzen, THF, dioxan, diethylether, diglyme, methyl-tert-butylether (MTBE), tert-amyl-methylether (TAME), dimethylether (DME), 2-methyl-THF, acetonitril, butyronitril, toluen, xylen, mesitylen, anisol, ethylacetat, isopropylacetat, methanol, ethanol, propanol, butanol, ethylenglycol, ethylencarbonat, propylencarbonat, N,N-dimethylacetamid, N,N-dimethylformamid, N-methylpyrrolidon, vand og blandinger heraf.
  9. 9. Fremgangsmåde ifølge et af kravene 1 til 8, idet overgangsmetalkatalysatoren er udvalgt af overgangsmetallerne M, idet M er udvalgt af Ni, Pd, Pt, Cu, Ag, Au, Co, Rh, Ir, Fe, Ru, Mn, Cr og Ti.
  10. 10. Fremgangsmåde ifølge et af kravene 1 til 8, idet overgangsmetalkatalysatoren er udvalgt af overgangsmetalsaltene MYP, idet M er udvalgt af Ni, Pd, Pt, Cu, Ag, Au, Co, Rh, Ir, Fe, Ru, Mn, Cr og Ti; Y uafhængigt af hinanden er udvalgt af F, Cl, Br, I, OTf, OAc, OMes, OTos, CF3CO2, SO4 og acetylacetonat; p er udvalgt af 1, 2, 3, 4, 5 og 6.
  11. 11. Fremgangsmåde ifølge et af kravene 1 til 8, idet overgangsmetalkatalysatoren er udvalgt af overgangsmetalkomplekserne MYpLr, idet M er udvalgt af Ni, Pd, Pt, Cu, Ag, Au, Co, Rh, Ir, Fe, Ru, Mn, Cr og Ti; Y uafhængigt af hinanden er udvalgt af F, Cl, Br, I, OTf, OAc, OMes, OTos, CF3CO2, SO4 og acetylacetonat; p er udvalgt af 1, 2, 3, 4, 5 og 6; L uafhængigt af hinanden er udvalgt af Cp (cyclopentadienid), Cp*(pentamethylcyclopentadienid), p-cymol, PR'3 og phosphoramidat; R' uafhængigt af hinanden er udvalgt af Ci-6-alkyl-, C3-5-cycloalkyl, C6-i2-aryl, Ci2-24-biaryl og phosphinoferrocenligander; og r er udvalgt af 0, 1, 2, 3, 4, 5 og 6.
  12. 12. Fremgangsmåde ifølge et af kravene 1 til 11, idet det i det mindste ene oxidationsmiddel er udvalgt af benzoquinon, luftens oxygen, O2, AgNO3, AgOAc, Cu(OAc)2, Ag2CO3, AgSbF6, K2S2O8, H4PM011VO40, Cu (OTf) 2 og Na2S2O8.
  13. 13. Fremgangsmåde ifølge et af kravene 1 til 12, idet de et til fem additiver er udvalgt af pTsOH, AcOH, TFA, CsOPiv, PivOH, KPF6, PPh3, NH4PF6 og NaBF4.
  14. 14. Fremgangsmåde ifølge et af kravene 1 til 13, idet arenet med formel (I) eller arenet med formel (II), fortrinsvis arenet med formel (II), anvendes i stort overskud som opløsningsmiddel.
DK13742231.7T 2012-08-02 2013-07-29 Fremgangsmåde til fremstilling af substituerede biphenyler ved hjælp af c-h-aktivering DK2880013T3 (da)

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EP12179058 2012-08-02
PCT/EP2013/065925 WO2014019995A1 (de) 2012-08-02 2013-07-29 Verfahren zum herstellen von substituierten biphenylen durch c-h-aktivierung

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US (1) US9199915B2 (da)
EP (1) EP2880013B1 (da)
JP (1) JP6109938B2 (da)
KR (1) KR102125294B1 (da)
CN (1) CN104520267B (da)
BR (1) BR112015002355B1 (da)
DK (1) DK2880013T3 (da)
ES (1) ES2681026T3 (da)
IN (1) IN2015DN00665A (da)
MX (1) MX365072B (da)
TW (1) TWI589551B (da)
WO (1) WO2014019995A1 (da)

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EP3009420A1 (de) 2014-10-16 2016-04-20 Bayer CropScience AG Verfahren zum Herstellen von Biphenylaminen aus Aniliden durch Rutheniumkatalyse
KR20160148589A (ko) 2014-04-25 2016-12-26 바이엘 크롭사이언스 악티엔게젤샤프트 루테늄 촉매반응에 의한 아닐리드로부터 비페닐아민의 제조방법
CN104557589A (zh) * 2014-12-24 2015-04-29 天津大学 N-(1，1’-二芳基)取代的酰胺类衍生物的制备方法
CN109678911B (zh) * 2019-02-01 2021-11-02 中国科学院上海有机化学研究所 二茂铁化合物及其制备方法
CN113563147B (zh) * 2021-07-29 2023-05-09 西湖大学 一种芳环苄位碳氢键选择性氘代的方法
CN113999130B (zh) * 2021-11-26 2023-09-29 湖北工业大学 一种邻硝基酰基苯胺类化合物的制备方法

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EP2119697A1 (en) * 2008-05-09 2009-11-18 Bayer CropScience AG Process for preparing substituted biphenylanilides
KR101751249B1 (ko) 2009-08-31 2017-06-27 바이엘 인텔렉쳐 프로퍼티 게엠베하 테트라아릴보레이트를 사용한 치환된 비페닐의 제조 방법
CN102005625A (zh) * 2010-09-28 2011-04-06 苏州群瑞环保科技有限公司 一种废旧锂电池处理的工艺方法

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CN104520267B (zh) 2017-07-14
US20150203440A1 (en) 2015-07-23
IN2015DN00665A (da) 2015-06-26
TW201434801A (zh) 2014-09-16
MX365072B (es) 2019-05-22
EP2880013B1 (de) 2018-05-09
JP6109938B2 (ja) 2017-04-05
TWI589551B (zh) 2017-07-01
ES2681026T3 (es) 2018-09-11
US9199915B2 (en) 2015-12-01
WO2014019995A1 (de) 2014-02-06
BR112015002355A2 (pt) 2017-07-04
JP2015524814A (ja) 2015-08-27
CN104520267A (zh) 2015-04-15
BR112015002355B1 (pt) 2020-04-14
KR102125294B1 (ko) 2020-06-23
KR20150036246A (ko) 2015-04-07
EP2880013A1 (de) 2015-06-10

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