A New Route to Acyclic Diaminocarbenes via Lithium-Halogen Exchange

被引：31

作者：

Snead, David R. ^{[1
]}

Ghiviriga, Ion ^{[1
]}

Abboud, Khalil A. ^{[1
]}

Hong, Sukwon ^{[1
]}

机构：

[1] Univ Florida, Dept Chem, Gainesville, FL 32611 USA

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 15期

关键词：

RHODIUM-CATALYZED ADDITION; N-HETEROCYCLIC CARBENES; CROSS-COUPLING REACTIONS; ARYLBORONIC ACIDS; METAL-COMPLEXES; ORGANOBORONIC ACIDS; OXIDATIVE ADDITION; STABLE CARBENES; ALDEHYDES; PALLADIUM;

D O I：

10.1021/ol9013156

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A lithium-halogen exchange route has been developed to generate acyclic diaminocarbenes (ADC) from chloroamidinium salts. Convenient access to various ADC complexes (B, Rh, Ir, Pd) stems from a one-pot transmetalation protocol. Formation of a carbenoid species is suggested by 1D and 2D NMR studies with a C-13-labeled chloroamidinium precursor and also by X-ray structures of transition metal-carbene complexes. Rh-ADC complex 4 is an effective catalyst for the 1,2-addition of aryl boronic acids to aryl aldehydes.

引用

页码：3274 / 3277

页数：4

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