Issue 60, 2019
From the journal:

Chemical Communications

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

Zi-Chao Wang,ab   Di Shen,ab   Jian Gao,ab   Xian Jia,a   Youjun Xu ORCID logo *a  and  Shi-Liang Shi ORCID logo *b  

* Corresponding authors

a School of Pharmaceutical Engineering, and Key Laboratory of Structure-Based Drug Design & Discovery (Ministry of Education), Shenyang Pharmaceutical University, Shenyang 110016, China
E-mail: xuyoujun@syphu.edu.cn

b State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China
E-mail: shiliangshi@sioc.ac.cn

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

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Article information

DOI
https://doi.org/10.1039/C9CC03459E
Article type
Communication
Submitted
05 mei 2019
Accepted
30 mei 2019
First published
30 mei 2019

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

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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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