American Chemical Society
ol8b02336_si_001.pdf (9.14 MB)

Palladium-Catalyzed anti-Selective Fluoroalkylboration of Internal and Terminal Alkynes

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journal contribution
posted on 2018-09-05, 17:52 authored by Shuaifeng Wang, Jian Zhang, Lichun Kong, Ze Tan, Yihui Bai, Gangguo Zhu
A Pd-catalyzed anti-stereospecific alkyne fluoroalkylboration, including mono-, di-, and perfluoroalkylboration, has been developed with fluoroalkyl halides and diboron reagents. The reaction is effective for both internal and terminal alkynes. It provides straightforward and streamlined access to functionalized 1,2-fluoroalkyl­boronated alkenes in a highly regio- and stereocontrolled manner. Preliminary studies suggest that this reaction is enabled by the combination of radical alkylation and metal-catalyzed borylation, thus leading to the realization of three-component trans-carboboration of alkynes for the first time.