期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 55, 期 14, 页码 4492-4496出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201511847
关键词
arenes; cross-coupling; electron transfer; radicals; reaction mechanisms
资金
- University of Strathclyde
- GlaxoSmithKline
Transition metal-free couplings of haloarenes with arenes, triggered by the use of alkali metal alkoxides in the presence of an organic additive, are receiving significant attention in the literature. Most of the known organic additives effect coupling of iodoarenes, but not bromoarenes, to arenes. Recently it was reported that 2-pyridinecarbinol (11) extends the reaction to aryl bromides. This paper investigates the mechanism, and reports evidence for dianions derived from 11 as electron donors to initiate the reaction. It also proposes routes by which electron-poor benzoyl derivatives can be transformed into electron donors to initiate these reactions.
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