Murahashi Cross-Coupling at-78 °C: A One-Pot Procedure for Sequential C-C/C-C, C-C/C-N, and C-C/C-S Cross-Coupling of Bromo-Chloro-Arenes

被引：21

作者：

Sinha, Narayan ^{[1
,3
,4
]}

Heijnen, Dorus ^{[1
,2
]}

Feringa, Ben L. ^{[2
]}

Organ, Michael G. ^{[1
,3
,4
]}

机构：

[1] York Univ, Dept Chem, 4700 Keele St, Toronto, ON M3J 1P3, Canada

[2] Univ Groningen, Stratingh Inst Chem, Nijenborgh 4, NL-9747 AG Groningen, Netherlands

[3] Univ Ottawa, CCRI, Ottawa, ON K1N 6N5, Canada

[4] Univ Ottawa, Dept Chem & Biomol Sci, Ottawa, ON K1N 6N5, Canada

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2019年 / 25卷 / 39期

基金：

欧洲研究理事会;

关键词：

Murahashi coupling; organolithium; Pd catalysis; PEPPSI; sequential cross-coupling; ALKYL GRIGNARD-REAGENTS; PD-PEPPSI-IPENT; LOW-TEMPERATURE; ROOM-TEMPERATURE; EFFECTIVE CATALYST; NHC COMPLEXES; VINYL HALIDES; ARYL HALIDES; PD-PEPPSI-IPENT(CL); HETEROCYCLES;

D O I：

10.1002/chem.201901678

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The coupling of organolithium reagents, including strongly hindered examples, at cryogenic temperatures (as low as -78 degrees C) has been achieved with high-reactivity Pd-NHC catalysts. A temperature-dependent chemoselectivity trigger has been developed for the selective coupling of aryl bromides in the presence of chlorides. Building on this, a one-pot, sequential coupling strategy is presented for the rapid construction of advanced building blocks. Importantly, one-shot addition of alkyllithium compounds to Pd cross-coupling reactions has been achieved, eliminating the need for slow addition by syringe pump.

引用

页码：9180 / 9184

页数：5

共 80 条

[31] Palladium-Catalyzed C(sp3) C(sp2) Cross-Coupling of (Trimethylsilyl)methyllithium with (Hetero)Aryl Halides [J].