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.
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收藏
页码：3274 / 3277
页数：4
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