期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 59, 期 22, 页码 8502-8506出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202002246
关键词
1; 2-migration; boronic esters; fluorocarbanions; fluoromethylation; stereospecificity
资金
- University of Bristol [EP/R513179/1]
- Alexander von Humboldt Stiftung
There is considerable interest in incorporating fluorine into agrochemicals and pharmaceuticals to improve their biological properties. Whilst a number of methods have been reported for installing CH2F and CHF2 groups, they are mainly limited to radical reactions, which are invariably racemic. Herein, we report the divergent, stereospecific reaction of fluoroiodomethyllithium with boronic esters to give alpha-fluoro-boronic esters. These unique intermediates can be readily transformed into the corresponding mono- or difluoromethylated compounds through proto- or fluorodeboronation, respectively. The use of the highly unstable fluoroiodomethyllithium was key to allowing rapid 1,2-migration over competing decomposition of the carbanion. DFT calculations informed and supported the experimental findings.
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