Issue 39, 2021

Nickel-catalyzed enantioselective 1,2-vinylboration of styrenes

Abstract

A novel nickel-catalyzed asymmetric 1,2-vinylboration reaction has been developed to afford benzylic alkenylboration products with high yields and excellent enantioselectivities by using a chiral bisoxazoline ligand. Under optimized conditions, a wide variety of chiral 2-boryl-1,1-arylvinylalkanes are efficiently prepared from readily available olefins and vinyl halides in the presence of bis(pinacolato)diboron as the boron source in a mild and easy-to-operate manner. This three-component cascade protocol furnishes exceptional chemo- and stereoselectivity, and its usefulness is illustrated by its application in asymmetric modifications of several structurally complex natural products and pharmaceuticals.

Graphical abstract: Nickel-catalyzed enantioselective 1,2-vinylboration of styrenes

Supplementary files

Article information

Article type
Edge Article
Submitted
24 Jul 2021
Accepted
07 Sep 2021
First published
07 Sep 2021
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2021,12, 13209-13215

Nickel-catalyzed enantioselective 1,2-vinylboration of styrenes

Y. Ye, J. Liu, B. Xu, S. Jiang, R. Bai, S. Li, T. Xie and X. Ye, Chem. Sci., 2021, 12, 13209 DOI: 10.1039/D1SC04071E

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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