Organozinc-Mediated Direct C-C Bond Formation via C-N Bond Cleavage of Ammonium Salts

被引：15

作者：

Wang, Dong-Yu ^{[1
,2
,3
,4
,5
]}

Morimoto, Koki ^{[1
]}

Yang, Ze-Kun ^{[1
,2
,3
]}

Wang, Chao ^{[1
,2
,3
]}

Uchiyama, Masanobu ^{[1
,2
,3
]}

机构：

[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, 7-3-1 Hongo, Tokyo To 1130033, Japan

[2] RIKEN, Adv Elements Chem Res Team, RIKEN Ctr Sustainable Resource Sci, 2-1 Hirosawa, Wako, Saitama 3510198, Japan

[3] RIKEN, Elements Chem Lab, 2-1 Hirosawa, Wako, Saitama 3510198, Japan

[4] Chinese Acad Sci, Shanghai Inst Mat Med, CAS Key Lab Receptor Res, 555 Zu Chong Zhi Rd, Shanghai 201203, Peoples R China

[5] Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, 555 Zu Chong Zhi Rd, Shanghai 201203, Peoples R China

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2017年 / 12卷 / 19期

关键词：

chemoselectivity; C-N bond cleavage; cross-coupling; organozinc; single electron transfer; SINGLE-ELECTRON-TRANSFER; CROSS-COUPLING REACTIONS; ARYL GRIGNARD-REAGENTS; ARYLTRIMETHYLAMMONIUM IODIDES; NICKEL-COMPLEXES; ALKENYL HALIDES; ZINC REAGENTS; BORYLATION; ARYLSTANNANES; ACTIVATION;

D O I：

10.1002/asia.201701132

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We report a direct cross-coupling reaction between diarylzinc (Ar2Zn) and aryltrimethylammonium salts (ArNMe3+center dot-OTf) in the presence of LiCl, via C-N bond cleavage. The reaction takes place smoothly upon heating in THF without any external catalyst, enabling an efficient and chemoselective formation of biaryl products. Mechanistic studies indicate that the reaction proceeds through a single electron transfer route.

引用

页码：2554 / 2557

页数：4

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