KR102125294B1 - C-h 활성화에 의한 치환된 비페닐의 제조 방법 - Google Patents

C-h 활성화에 의한 치환된 비페닐의 제조 방법 Download PDF

Info

Publication number
KR102125294B1
KR102125294B1 KR1020157002343A KR20157002343A KR102125294B1 KR 102125294 B1 KR102125294 B1 KR 102125294B1 KR 1020157002343 A KR1020157002343 A KR 1020157002343A KR 20157002343 A KR20157002343 A KR 20157002343A KR 102125294 B1 KR102125294 B1 KR 102125294B1
Authority
KR
South Korea
Prior art keywords
formula
group
transition metal
iva
ivb
Prior art date
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 - Fee Related
Application number
KR1020157002343A
Other languages
English (en)
Korean (ko)
Other versions
KR20150036246A (ko
Inventor
마티아스 리드리히
라르스 로데펠트
프랑크 볼츠
Original Assignee
바이엘 크롭사이언스 악티엔게젤샤프트
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.)
Filing date
Publication date
Application filed by 바이엘 크롭사이언스 악티엔게젤샤프트 filed Critical 바이엘 크롭사이언스 악티엔게젤샤프트
Publication of KR20150036246A publication Critical patent/KR20150036246A/ko
Application granted granted Critical
Publication of KR102125294B1 publication Critical patent/KR102125294B1/ko
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00Preparation of carboxylic acid amides
    • C07C231/12Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0201Oxygen-containing compounds
    • B01J31/0202Alcohols or phenols
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22Organic complexes
    • B01J31/2204Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208Oxygen, e.g. acetylacetonates
    • B01J31/2226Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
    • B01J31/223At least two oxygen atoms present in one at least bidentate or bridging ligand
    • B01J31/2239Bridging ligands, e.g. OAc in Cr2(OAc)4, Pt4(OAc)8 or dicarboxylate ligands
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22Organic complexes
    • B01J31/2282Unsaturated compounds used as ligands
    • B01J31/2295Cyclic compounds, e.g. cyclopentadienyls
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/44Compounds 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
    • C07C211/45Monoamines
    • C07C211/48N-alkylated amines
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00Carboxylic acid amides
    • C07C233/01Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/12Carboxylic 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
    • C07C233/15Carboxylic 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
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/40Substitution 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
    • B01J2231/42Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
    • B01J2231/4205C-C cross-coupling, e.g. metal catalyzed or Friedel-Crafts type
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/10Complexes comprising metals of Group I (IA or IB) as the central metal
    • B01J2531/16Copper
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82Metals of the platinum group
    • B01J2531/822Rhodium

Landscapes

  • 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)
KR1020157002343A 2012-08-02 2013-07-29 C-h 활성화에 의한 치환된 비페닐의 제조 방법 Expired - Fee Related KR102125294B1 (ko)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP12179058 2012-08-02
EP12179058.8 2012-08-02
PCT/EP2013/065925 WO2014019995A1 (de) 2012-08-02 2013-07-29 Verfahren zum herstellen von substituierten biphenylen durch c-h-aktivierung

Publications (2)

Publication Number Publication Date
KR20150036246A KR20150036246A (ko) 2015-04-07
KR102125294B1 true KR102125294B1 (ko) 2020-06-23

Family

ID=48877252

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1020157002343A Expired - Fee Related KR102125294B1 (ko) 2012-08-02 2013-07-29 C-h 활성화에 의한 치환된 비페닐의 제조 방법

Country Status (12)

Country Link
US (1) US9199915B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
EP (1) EP2880013B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
JP (1) JP6109938B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
KR (1) KR102125294B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
CN (1) CN104520267B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
BR (1) BR112015002355B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
DK (1) DK2880013T3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
ES (1) ES2681026T3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
IN (1) IN2015DN00665A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
MX (1) MX365072B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
TW (1) TWI589551B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
WO (1) WO2014019995A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2799722T3 (es) * 2014-04-25 2020-12-21 Bayer Cropscience Ag Procedimiento para preparar bifenilaminas a partir de anilidas por catálisis con rutenio
EP3009420A1 (de) 2014-10-16 2016-04-20 Bayer CropScience AG Verfahren zum Herstellen von Biphenylaminen aus Aniliden durch Rutheniumkatalyse
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

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2119697A1 (en) * 2008-05-09 2009-11-18 Bayer CropScience AG Process for preparing substituted biphenylanilides
IN2012DN02002A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 2009-08-31 2015-07-24 Bayer Cropscience Ag
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

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
논문 Angew. Chem. Int. Ed., Vol. 51, pp. 2247-2251 (2012)*
논문 Organic Letters, Vol. 10, No. 11, pp. 2207-2210 (2008)*

Also Published As

Publication number Publication date
TWI589551B (zh) 2017-07-01
EP2880013A1 (de) 2015-06-10
KR20150036246A (ko) 2015-04-07
MX365072B (es) 2019-05-22
JP2015524814A (ja) 2015-08-27
MX2015001459A (es) 2015-05-08
WO2014019995A1 (de) 2014-02-06
EP2880013B1 (de) 2018-05-09
DK2880013T3 (en) 2018-08-06
CN104520267B (zh) 2017-07-14
CN104520267A (zh) 2015-04-15
TW201434801A (zh) 2014-09-16
BR112015002355A2 (pt) 2017-07-04
ES2681026T3 (es) 2018-09-11
JP6109938B2 (ja) 2017-04-05
US9199915B2 (en) 2015-12-01
BR112015002355B1 (pt) 2020-04-14
IN2015DN00665A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 2015-06-26
US20150203440A1 (en) 2015-07-23

Similar Documents

Publication Publication Date Title
KR102125294B1 (ko) C-h 활성화에 의한 치환된 비페닐의 제조 방법
US20110003999A1 (en) Process for Preparing Substituted Biphenylanilides
US7709684B2 (en) Process for preparing substituted biphenyls
KR102310474B1 (ko) 염소화 비페닐아닐리드 및 비페닐아닐린의 개선된 제조방법
MX2007009457A (es) Procedimiento para la preparacion de bifenilos sustituidos.
US20100185015A1 (en) Process for preparing biaryls
CN102076651A (zh) 制备取代联苯的方法
JP2019504883A (ja) ピラゾールを調製する接触水素化方法
CN102325747B (zh) 制备2-氨基联苯类化合物的方法
MX2014009442A (es) Enaminocetonas que contienen cf3o y su uso para la preparacion de pirazoles que contienen cf3o.
DK2473476T3 (en) Tetraarylborat method for producing substituted biphenyls
EP2257530B1 (en) Process for preparing substituted biphenylanilides
CN101589016A (zh) 制备取代的2-芳基丙二酸酯的方法

Legal Events

Date Code Title Description
PA0105 International application

St.27 status event code: A-0-1-A10-A15-nap-PA0105

PG1501 Laying open of application

St.27 status event code: A-1-1-Q10-Q12-nap-PG1501

R18-X000 Changes to party contact information recorded

St.27 status event code: A-3-3-R10-R18-oth-X000

P11-X000 Amendment of application requested

St.27 status event code: A-2-2-P10-P11-nap-X000

P13-X000 Application amended

St.27 status event code: A-2-2-P10-P13-nap-X000

PA0201 Request for examination

St.27 status event code: A-1-2-D10-D11-exm-PA0201

R17-X000 Change to representative recorded

St.27 status event code: A-3-3-R10-R17-oth-X000

P22-X000 Classification modified

St.27 status event code: A-2-2-P10-P22-nap-X000

D13-X000 Search requested

St.27 status event code: A-1-2-D10-D13-srh-X000

D14-X000 Search report completed

St.27 status event code: A-1-2-D10-D14-srh-X000

E902 Notification of reason for refusal
PE0902 Notice of grounds for rejection

St.27 status event code: A-1-2-D10-D21-exm-PE0902

E13-X000 Pre-grant limitation requested

St.27 status event code: A-2-3-E10-E13-lim-X000

P11-X000 Amendment of application requested

St.27 status event code: A-2-2-P10-P11-nap-X000

P13-X000 Application amended

St.27 status event code: A-2-2-P10-P13-nap-X000

E701 Decision to grant or registration of patent right
PE0701 Decision of registration

St.27 status event code: A-1-2-D10-D22-exm-PE0701

GRNT Written decision to grant
PR0701 Registration of establishment

St.27 status event code: A-2-4-F10-F11-exm-PR0701

PR1002 Payment of registration fee

St.27 status event code: A-2-2-U10-U12-oth-PR1002

Fee payment year number: 1

PG1601 Publication of registration

St.27 status event code: A-4-4-Q10-Q13-nap-PG1601

PC1903 Unpaid annual fee

St.27 status event code: A-4-4-U10-U13-oth-PC1903

Not in force date: 20230617

Payment event data comment text: Termination Category : DEFAULT_OF_REGISTRATION_FEE

PC1903 Unpaid annual fee

St.27 status event code: N-4-6-H10-H13-oth-PC1903

Ip right cessation event data comment text: Termination Category : DEFAULT_OF_REGISTRATION_FEE

Not in force date: 20230617