期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 55, 期 38, 页码 11629-11632出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201605651
关键词
alkenes; C-C coupling; fluorine; palladium; synthetic methods
资金
- NIGMS [R35 GM118190]
The palladium-catalyzed defluorinative coupling of 1-aryl-2,2-difluoroalkenes with boronic acids is described. Broad functional-group tolerance arises from a redox-neutral process by a palladium(II) active species which is proposed to undergo a -fluoride elimination to afford the products. The monofluorostilbene products were formed with excellent diastereoselectivity (50:1) in all cases, and it is critical, as traditional chromatographic techniques often fail to separate monofluoroalkene isomers. As a demonstration of this method's unique combination of reactivity and functional-group tolerance, a Gleevec (R) analogue, using a monofluorostilbene as an amide isostere, was synthesized.
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