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Issue 60, 2019

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

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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


Submitted
05 May 2019
Accepted
30 May 2019
First published
30 May 2019

Chem. Commun., 2019,55, 8848-8851
Article type
Communication

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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