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

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

A first example of Pd-catalyzed gem-difluoroallylation of organoborons using 3-bromo-3,3-difluoropropene (BDFP) in high efficiency with high α/γ-substitution regioselectivity has been developed. The reaction can also be extended to substituted BDFPs and has advantages of low catalyst loading (0.8 to...

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Veröffentlicht in:Journal of the American Chemical Society 2014-01, Vol.136 (4), p.1230-1233
Hauptverfasser: Min, Qiao-Qiao, Yin, Zengsheng, Feng, Zhang, Guo, Wen-Hao, Zhang, Xingang
Format: Artikel
Sprache:eng
Schlagworte:
Alkenes - chemistry
Boron Compounds - chemistry
Catalysis
Hydrocarbons, Halogenated - chemical synthesis
Hydrocarbons, Halogenated - chemistry
Molecular Structure
Organometallic Compounds - chemistry
Palladium - chemistry
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Zusammenfassung:A first example of Pd-catalyzed gem-difluoroallylation of organoborons using 3-bromo-3,3-difluoropropene (BDFP) in high efficiency with high α/γ-substitution regioselectivity has been developed. The reaction can also be extended to substituted BDFPs and has advantages of 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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja4114825