Reductive Coupling of Aryl Halides via C-H Activation of Indene

被引：13

作者：

Zhang, Bo-Sheng ^{[1
]}

Yang, Ying-Hui ^{[1
]}

Wang, Fan ^{[1
]}

Gou, Xue-Ya ^{[2
]}

Wang, Xi-Cun ^{[1
]}

Liang, Yong-Min ^{[2
]}

Li, Yuke ^{[3
,4
]}

Quan, Zheng-Jun ^{[1
]}

机构：

[1] Northwest Normal Univ, Coll Chem & Chem Engn, Gansu Int Sci & Technol Cooperat Base Water Reten, Lanzhou 730070, Gansu, Peoples R China

[2] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China

[3] Chinese Univ Hong Kong, Dept Chem, Shatin, Hong Kong, Peoples R China

[4] Chinese Univ Hong Kong, Ctr Sci Modeling & Computat, Shatin, Hong Kong, Peoples R China

来源：

CHINESE JOURNAL OF CHEMISTRY | 2021年 / 39卷 / 06期

基金：

中国国家自然科学基金;

关键词：

C— C coupling; Palladium; Reduction; Indene; H activation; BOND FORMATION; NICKEL; BIARYLS; FUNCTIONALIZATION; ALKENYLATION; VERSATILE; IODIDES; PD;

D O I：

10.1002/cjoc.202100034

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Main observation and conclusion This paper describes the first case of a reductive coupling reaction with indene, a non-heteroatom olefin used as a reducing agent. The scope of the substrate is wide. The homo-coupling, cross-coupling, and synthesis of 12 and 14-membered rings were realized. The control experiment, indene-product curve and density functional theory calculations showed that the eta(3)-palladium indene intermediate was formed by C-H activation in the presence of cesium carbonate. We speculate that the final product was obtained through a Pd (IV) intermediate or aryl ligand exchange. In addition, we excluded the formation of palladium anion (Pd(0)(-)) intermediates.

引用

页码：1573 / 1579

页数：7

共 50 条

[1] Multimetallic catalysed cross-coupling of aryl bromides with aryl triflates [J].

Ackerman, Laura K. G. ;

Lovell, Matthew M. ;

Weix, Daniel J. .

NATURE, 2015, 524 (7566) :454-+

[2] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].

Alberico, Dino ;

Scott, Mark E. ;

Lautens, Mark .

CHEMICAL REVIEWS, 2007, 107 (01) :174-238

[3] Nickel-Catalyzed Asymmetric Reductive Diarylation of Vinylarenes [J].

Anthony, David ;

Lin, Qiao ;

Baudet, Judith ;

Diao, Tianning .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (10) :3198-3202

[4] Kumada-Grignard-type biaryl couplings on water [J].

Bhattacharjya, Anish ;

Klumphu, Piyatida ;

Lipshutz, Bruce H. .

NATURE COMMUNICATIONS, 2015, 6

[5] Organic Electron Donors as Powerful Single-Electron Reducing Agents in Organic Synthesis [J].

Broggi, Julie ;

Terme, Thierry ;

Vanelle, Patrice .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (02) :384-413

[6] Selective Ortho Thiolation Enabled by Tuning the Ancillary Ligand in Palladium/Norbornene Catalysis [J].

Cai, Wenqiang ;

Gu, Zhenhua .

ORGANIC LETTERS, 2019, 21 (09) :3204-3209

[7] Exploiting the Chemistry of Strained Rings: Synthesis of Indoles via Domino Reaction of Aryl Iodides with 2H-Azirines [J].

Candito, David A. ;

Lautens, Mark .

ORGANIC LETTERS, 2010, 12 (15) :3312-3315

[8] Analysis of the reactions used for the preparation of drug candidate molecules [J].

Carey, John S. ;

Laffan, David ;

Thomson, Colin ;

Williams, Mike T. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (12) :2337-2347

[9] A complex catalytic cycle leading to a regioselective synthesis of o,o'-disubstituted vinylarenes [J].

Catellani, M ;

Frignani, F ;

Rangoni, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (1-2) :119-122

[10] Palladium(II)-Initiated Catellani-Type Reactions [J].

Cheng, Hong-Gang ;

Chen, Shuqing ;

Chen, Ruiming ;

Zhou, Qianghui .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (18) :5832-5844

← 1 2 3 4 5 →