Issue 60, 2019

Base-catalysed reductive relay hydroboration of allylic alcohols with pinacolborane to form alkylboronic esters

Abstract

An unprecedented base-catalysed reductive relay hydroboration of allylic alcohols is described. Commercially available nBuLi was found to be a robust transition metal-free initiator for this protocol, affording various boronic esters in high yield and selectivity. Mechanistically, this methodology involves a one-pot three-step successive process (dehydrocoupling/allylic hydride substitution/anti-Markovnikov hydroboration).

Graphical abstract: Base-catalysed reductive relay hydroboration of allylic alcohols with pinacolborane to form alkylboronic esters

Supplementary files

Article information

Article type
Communication
Submitted
05 mei 2019
Accepted
30 mei 2019
First published
30 mei 2019

Chem. Commun., 2019,55, 8848-8851

Base-catalysed reductive relay hydroboration of allylic alcohols with pinacolborane to form alkylboronic esters

Z. Wang, D. Shen, J. Gao, X. Jia, Y. Xu and S. Shi, Chem. Commun., 2019, 55, 8848 DOI: 10.1039/C9CC03459E

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