CN104520267B - 通过c‑h活化制备取代联苯的方法 - Google Patents

通过c‑h活化制备取代联苯的方法 Download PDF

Info

Publication number
CN104520267B
CN104520267B CN201380041158.7A CN201380041158A CN104520267B CN 104520267 B CN104520267 B CN 104520267B CN 201380041158 A CN201380041158 A CN 201380041158A CN 104520267 B CN104520267 B CN 104520267B
Authority
CN
China
Prior art keywords
formula
group
methyl
iii
groups
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
CN201380041158.7A
Other languages
English (en)
Chinese (zh)
Other versions
CN104520267A (zh
Inventor
M·瑞德里希
L·瑞德费尔德
F·沃尔兹
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.)
Bayer CropScience AG
Original Assignee
Bayer CropScience AG
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 Bayer CropScience AG filed Critical Bayer CropScience AG
Publication of CN104520267A publication Critical patent/CN104520267A/zh
Application granted granted Critical
Publication of CN104520267B publication Critical patent/CN104520267B/zh
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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

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)
CN201380041158.7A 2012-08-02 2013-07-29 通过c‑h活化制备取代联苯的方法 Expired - Fee Related CN104520267B (zh)

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
CN104520267A CN104520267A (zh) 2015-04-15
CN104520267B true CN104520267B (zh) 2017-07-14

Family

ID=48877252

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201380041158.7A Expired - Fee Related CN104520267B (zh) 2012-08-02 2013-07-29 通过c‑h活化制备取代联苯的方法

Country Status (12)

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

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3009420A1 (de) 2014-10-16 2016-04-20 Bayer CropScience AG Verfahren zum Herstellen von Biphenylaminen aus Aniliden durch Rutheniumkatalyse
US10246407B2 (en) 2014-04-25 2019-04-02 Bayer Cropscience Aktiengesellschaft Process for preparing biphenylamines from anilides by ruthenium catalysis
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

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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

Family Cites Families (2)

* 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
ES2534557T3 (es) 2009-08-31 2015-04-24 Bayer Intellectual Property Gmbh Procedimiento de tetraarilborato para la preparación de bifenilos sustituidos

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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 (3)

* Cited by examiner, † Cited by third party
Title
[RhIIICp*]-Catalyzed Dehydrogenative Aryl_Aryl Bond Formation;Joanna Wencel-Delord等;《Angew. Chem. Int. Ed.》;20120227;第51卷;第2247 –2251页 *
Bi-Jie Li.Multiple C H Activations To Construct Biologically Active Molecules in a Process Completely Free of Organohalogen and Organometallic Components.《Angew. Chem. Int. Ed》.2008,第47卷第1115-1118页. *
Twofold C-H Functionalization:Palladium-Catalyzed Ortho Arylation of;Gordon Brasche等;《ORGANIC LETTERS》;20080905;第10卷(第11期);第2207-2210页 *

Also Published As

Publication number Publication date
EP2880013B1 (de) 2018-05-09
US9199915B2 (en) 2015-12-01
IN2015DN00665A (enExample) 2015-06-26
KR102125294B1 (ko) 2020-06-23
BR112015002355B1 (pt) 2020-04-14
US20150203440A1 (en) 2015-07-23
JP6109938B2 (ja) 2017-04-05
BR112015002355A2 (pt) 2017-07-04
WO2014019995A1 (de) 2014-02-06
CN104520267A (zh) 2015-04-15
EP2880013A1 (de) 2015-06-10
JP2015524814A (ja) 2015-08-27
DK2880013T3 (en) 2018-08-06
TW201434801A (zh) 2014-09-16
MX365072B (es) 2019-05-22
ES2681026T3 (es) 2018-09-11
MX2015001459A (es) 2015-05-08
KR20150036246A (ko) 2015-04-07
TWI589551B (zh) 2017-07-01

Similar Documents

Publication Publication Date Title
CN104520267B (zh) 通过c‑h活化制备取代联苯的方法
St John-Campbell et al. Transient imines as ‘next generation’directing groups for the catalytic functionalisation of C–H bonds in a single operation
Subaramanian et al. Recent advances in nickel-catalyzed C–C and C–N bond formation via HA and ADC reactions
Guyon et al. CF3SO2X (X= Na, Cl) as reagents for trifluoromethylation, trifluoromethylsulfenyl-,-sulfinyl-and-sulfonylation. Part 1: Use of CF3SO2Na
Nareddy et al. Ruthenium (II)-catalyzed regioselective C–H arylation of cyclic and N, N-dialkyl benzamides with boronic acids by weak coordination
Chen et al. The palladium-catalyzed desulfitative cyanation of arenesulfonyl chlorides and sodium sulfinates
Wang et al. Room temperature, open-flask C–H arylation of electron-deficient heteroarenes with triazenes: rapid synthesis of heterobiaryls
JP2019108352A (ja) ハロゲン化されたビフェニルアニリドおよびビフェニルアニリンの改善された製造方法
CN102076651A (zh) 制备取代联苯的方法
Tsang et al. Recent advances in rhodium-catalysed cross-dehydrogenative-coupling between two C (sp 2)–H bonds
CN102325747B (zh) 制备2-氨基联苯类化合物的方法
Erb et al. Functionalization of 3-Iodo-N, N-Diisopropylferrocene-Carboxamide, a Pivotal Substrate to Open the Chemical Space to 1, 3-Disubstituted Ferrocenes
TW202010741A (zh) 三環化合物製備方法
JP5355393B2 (ja) ハロベンゼン誘導体からアルキルアニリドを製造するための方法
CN108640945B (zh) 一种酰胺类化合物及其制备方法与应用
Shen et al. One-pot synthesis of 4 (3H)-quinazolinones from azides, alkynes, anilines, and carbon monoxide
CN102482195B (zh) 制备取代联苯的四芳基硼酸盐法
CN101952253B (zh) 取代的酰联苯胺的制备方法
Acharya et al. Transition Metal‐Catalyzed Directing Group‐Assisted Site‐Selective Di‐Ortho C H Functionalizations via Double C H Activation
Wessjohann et al. 1, 4-Addition of (Diphenylmethylene) amine to Acceptor Substituted Olefins. A Versatile Synthesis of Protected β-Amino Acids, Nitriles, and Ketones
CN101309907B (zh) 羧酰苯胺的制备方法
Fairlamb Transition metals in organic synthesis: cross-coupling and C–H activation processes
CN1934076B (zh) 制备缩氨基脲的方法
Fantoni Green approach to Palladium Cross-Coupling reactions and development of new methodologies based on highly abundant metals
Li Ruthenium (II)-Catalyzed Direct C− H meta-Alkylations, Alkenylations and Alkyne Annulations

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant
CF01 Termination of patent right due to non-payment of annual fee

Granted publication date: 20170714

CF01 Termination of patent right due to non-payment of annual fee