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Site-Fixed Hydroboration of Alkenes under Metal-Free Conditions: Scope and Mechanistic Studies

preprint
submitted on 12.01.2021, 15:12 and posted on 13.01.2021, 12:28 by Sida Li, Chenyang Hu, Xin Cui, Liu Leo Liu, Lipeng Wu
An unprecedented and general metal-free hydroboration of alkenes with BBr3 as the boration reagent in the presence of iPr2NEt is reported. The addition of iPr2NEt not only suppresses alkene oligomerization and bromoboration side reactions, but also provides a proton source for hydroboration. More importantly, the site-fixed installation of a boryl group at the original position of the internal double-bond is easily achieved using our strategy as compared with traditional transition-metal-catalyzed hydroboration processes. Preliminary studies on the mechanism revealed a distinct reaction pathway that involves radical species and may operate through frustrated-Lewispair-type single-electron transfer.

History

Email Address of Submitting Author

lipengwu@licp.cas.cn

Institution

Lanzhou Institute of Chemical Physics (LICP)

Country

China

ORCID For Submitting Author

0000-0003-0583-4832

Declaration of Conflict of Interest

The authors declare no competing interests.

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