Issue 22, 2021

Acrylic boronate: a multifunctional C3 building block for catalytic synthesis of rare organoborons and chemoselective heterobifunctional ligations

Abstract

A novel C3 acylboron building block; acrylic boronate was successfully prepared and its versatility for catalytic synthesis of several previously inaccessible organoborons is described. Cross-metathesis and Pd-catalyzed coupling of acrylic boronate enabled two complementary routes to highly functionalized α,β-unsaturated acylborons and two new types of conjugated borylated products: α,β,γ,δ-unsaturated and bis-α,β unsaturated acylborons. The synthetic application of α,β-unsaturated acylborons was demonstrated for the first time, thereby providing a general and highly regioselective route to medicinally important 3-boryl pyrazoles. Acrylic boronate also provided a unique bis-electrophilic platform for rapid and chemoselective labeling of cysteines with acylboron tags which are potentially useful for site-selective functionalization and orthogonal ligation of proteins.

Graphical abstract: Acrylic boronate: a multifunctional C3 building block for catalytic synthesis of rare organoborons and chemoselective heterobifunctional ligations

Supplementary files

Article information

Article type
Edge Article
Submitted
13 Feb 2021
Accepted
26 Apr 2021
First published
26 Apr 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-NC license

Chem. Sci., 2021,12, 7924-7929

Acrylic boronate: a multifunctional C3 building block for catalytic synthesis of rare organoborons and chemoselective heterobifunctional ligations

S. Lin, L. Wang and A. Sharma, Chem. Sci., 2021, 12, 7924 DOI: 10.1039/D1SC00905B

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