Copper-Catalyzed Cross-Coupling of Nonactivated Secondary Alkyl Halides and Tosylates with Secondary Alkyl Grignard Reagents

被引：159

作者：

Yang, Chu-Ting ^{[1
]}

Zhang, Zhen-Qi ^{[1
]}

Liang, Jun ^{[2
]}

Liu, Jing-Hui ^{[1
]}

Lu, Xiao-Yu ^{[2
]}

Chen, Huan-Huan ^{[2
]}

Liu, Lei ^{[1
]}

机构：

[1] Tsinghua Univ, Dept Chem, Tsinghua Peking Ctr Life Sci, Beijing 100084, Peoples R China

[2] Univ Sci & Technol China, Dept Chem, Hefei 230026, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 27期

关键词：

SUZUKI REACTIONS; SP(3) CARBON; ELECTROPHILES; BROMIDES; ARYL; IODOALKANES; CYCLIZATION; REACTIVITY; CHLORIDES; CENTERS;

D O I：

10.1021/ja304848n

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Practical catalytic cross-coupling of secondary alkyl electrophiles with secondary alkyl nucleophiles under Cu catalysis has been realized. The use of TMEDA and LiOMe is critical for the success of the reaction. This cross-coupling reaction occurs via an S(N)2 mechanism with inversion of configuration and therefore provides a general approach for the stereocontrolled formation of C-C bonds between two tertiary carbons from chiral secondary alcohols.

引用

页码：11124 / 11127

页数：4

共 50 条

[1] Copper-Catalyzed Cross-Coupling of Functionalized Alkyl Halides and Tosylates with Secondary and Tertiary Alkyl Grignard Reagents
Ren, Peng
Stern, Lucas-Alexandre
Hu, Xile
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (36) : 9110 - 9113
[2] Copper-Catalyzed Cross-Coupling of Alkyl and Aryl Grignard Reagents with Alkynyl Halides
Cahiez, Gerard
Gager, Olivier
Buendia, Julien
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (07) : 1278 - 1281
[3] Copper-Catalyzed Reductive Cross-Coupling of Nonactivated Alkyl Tosylates and Mesylates with Alkyl and Aryl Bromides
Liu, Jing-Hui
Yang, Chu-Ting
Lu, Xiao-Yu
Zhang, Zhen-Qi
Xu, Ling
Cui, Mian
Lu, Xi
Xiao, Bin
Fu, Yao
Liu, Lei
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (47) : 15334 - 15338
[4] Cross-Coupling of Nonactivated Primary and Secondary Alkyl Halides with Aryl Grignard Reagents Catalyzed by Chiral Iron Pincer Complexes
Bauer, Gerald
Cheung, Chi Wai
Hu, Xile
[J]. SYNTHESIS-STUTTGART, 2015, 47 (12): : 1726 - 1732
[5] Copper-Catalyzed Cross-Coupling between Alkyl (Pseudo)halides and Bicyclopentyl Grignard Reagents
Andersen, Claire
Ferey, Vincent
Daumas, Marc
Bernardelli, Patrick
Guerinot, Amandine
Cossy, Janine
[J]. ORGANIC LETTERS, 2020, 22 (15) : 6021 - 6025
[6] Copper-catalyzed cross-coupling of alkylsamarium reagents with alkyl halides
Berkowitz, WF
Wu, YZ
[J]. TETRAHEDRON LETTERS, 1997, 38 (18) : 3171 - 3174
[7] Mild and Phosphine-Free Iron-Catalyzed Cross-Coupling of Nonactivated Secondary Alkyl Halides with Alkynyl Grignard Reagents
Cheung, Chi Wai
Ren, Peng
Hu, Xile
[J]. ORGANIC LETTERS, 2014, 16 (09) : 2566 - 2569
[8] Iron-catalyzed cross-coupling of primary and secondary alkyl halides with aryl Grignard reagents
Nakamura, M
Matsuo, K
Ito, S
Nakamura, E
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (12) : 3686 - 3687
[9] Copper nanoparticle-catalyzed cross-coupling of alkyl halides with Grignard reagents
Kim, Ju Hyun
Chung, Young Keun
[J]. CHEMICAL COMMUNICATIONS, 2013, 49 (94) : 11101 - 11103
[10] An improved copper-catalyzed cross-coupling reaction of alkyl triflates with primary alkyl Grignard reagents
Wang, Shifa
Zhang, Aijun
[J]. ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2008, 40 (03) : 293 - 301

← 1 2 3 4 5 →