An unprecedented iron-catalyzed cross-coupling of primary and secondary alkyl Grignard reagents with non-activated aryl chlorides

被引:36
|
作者
Perry, Marc C. [1 ]
Gillett, Amber N. [1 ]
Law, Tyler C. [2 ]
机构
[1] Point Loma Nazarene Univ, Dept Chem, San Diego, CA 92106 USA
[2] Univ Alaska Anchorage, Dept Chem, Anchorage, AK 99508 USA
关键词
N-Heterocyclic carbenes; Grignard; Iron-catalyzed; Cross-coupling; BEARING BETA-HYDROGENS; CARBENE CATALYSTS; ORGANIC HALIDES; REACTIVITY; PHOSPHINE; COMPLEXES;
D O I
10.1016/j.tetlet.2012.06.048
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The use of N-heterocyclic carbene ligands in the iron-catalyzed cross-coupling of alkyl Grignards has allowed, for the first time, coupling of non-activated, electron rich aryl chlorides. Surprisingly, the tetrahydrate of FeCl2 was found to be a better pre-catalyst than anhydrous FeCl2. Primary Grignard reagents coupled in excellent yields while secondary Grignard reagents coupled in modest yields. The use of acyclic secondary Grignard reagents resulted in the formation of isomers in addition to the desired product. These isomeric products were formed via reversible beta-hydrogen elimination, indicating that the cross-coupling proceeds through an ionic pathway. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4436 / 4439
页数:4
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