N,N-Diethyl O-Carbamate: Directed Metalation Group and Orthogonal Suzuki-Miyaura Cross-Coupling Partner

被引：202

作者：

Antoft-Finch, Aurora ^{[1
]}

Blackburn, Tom ^{[1
]}

Snieckus, Victor ^{[1
]}

机构：

[1] Queens Univ, Dept Chem, Kingston, ON K7L 3N6, Canada

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 49期

基金：

加拿大自然科学与工程研究理事会;

关键词：

ANIONIC FRIES REARRANGEMENT; ARYL CARBON-OXYGEN; GRIGNARD-REAGENTS; ARYLBORONIC ACIDS; POLYSUBSTITUTED AROMATICS; ORGANOBORON COMPOUNDS; EFFICIENT SYNTHESIS; BORONIC ACIDS; NICKEL; BIARYLS;

D O I：

10.1021/ja907700e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) The first Suzuki-Miyaura cross-coupling of an aryl O-carbamate, a versatile and powerful directed metalation group (DMG) in directed ortho metalation (DoM) chemistry, is described using the inexpensive, bench-stable catalyst NiCl2(PCy3)2. Broad synthetic scope and good efficiency are demonstrated for aryl and heteroaryl O-carbamates. The role of water and hydrolysis equilibrium between free boronic acid and boroxine was established to be a crucial parameter for this transformation. When combined with DoM and traditional Pd-catalyzed Suzuki-Miyaura strategies, the methodology offers concise routes to uniquely substituted molecules, avoiding the need for protection/deprotection of the phenol and the use of strongly nucleophilic cross-coupling partners. © 2009 American Chemical Society.

引用

页码：17750 / 17752

页数：3

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