Radical Hydroboration and Hydrosilylation of gem-Difluoroalkenes: Synthesis of α‑Difluorinated Alkylborons and Alkylsilanes

A first example of radical hydroboration and hydrosilylation of gem-difluoroalkenes using ABIN as the radical initiator is described. This protocol features good functional group tolerance, operational simplicity, high atom economy, and easy scale-up, enabling efficient assembly of a wide range of α...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2019-10, Vol.21 (20), p.8454-8458
Main Authors: Liu, Xiaozu, Lin, E Emily, Chen, Guojun, Li, Ji-Lin, Liu, Peijun, Wang, Honggen
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A first example of radical hydroboration and hydrosilylation of gem-difluoroalkenes using ABIN as the radical initiator is described. This protocol features good functional group tolerance, operational simplicity, high atom economy, and easy scale-up, enabling efficient assembly of a wide range of α-difluorinated alkylborons and alkylsilanes in moderate to excellent yields. The synthetic utility of these products is demonstrated by further transformation of the C–B bond and C–Si bond into valuable CF2-containing molecules.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b03218