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Highly Selective gem-Difluoroallylation of Organoborons with Bromodifluoromethylated Alkenes Catalyzed by Palladium

Qiao-Qiao Min, Zengsheng Yin, Zhang Feng, Wen-Hao Guo and Xingang Zhang*

*Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China, Email: xgzhangmail.sioc.ac.cn

Q.-Q. Min, Z. Yin, Z. Feng, W.-H. Guo, X. Zhang, J. Am. Chem. Soc., 2014, 136, 1230-1233.

DOI: 10.1021/ja4114825


Abstract

A Pd-catalyzed gem-difluoroallylation of organoborons using 3-bromo-3,3-difluoropropene (BDFP) proceeds in high efficiency with high α/γ-substitution regioselectivity. The reaction offers low catalyst loading (0.8 to 0.01 mol %), broad substrate scope, and excellent functional group compatibility, thus providing a facile route for practical application in drug discovery and development.

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Key Words

allylation, benzyl fluorides, allyl fluorides


ID: J48-Y2014