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

Shengjia Lin, Lucia Wang, Abhishek Sharma

Research output: Contribution to journalArticlepeer-review

8 Scopus citations

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.

Original languageEnglish
Pages (from-to)7924-7929
Number of pages6
JournalChemical Science
Volume12
Issue number22
DOIs
StatePublished - 14 Jun 2021

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