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

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

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

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

Permissions

Request permissions

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements