Acrylic boronate: a multifunctional C3 building block for catalytic synthesis of rare organoborons and chemoselective heterobifunctional ligations. Issue 22 (11th May 2021)

• Record Type: Journal Article
• Authors: Lin, Shengjia; Wang, Lucia; Sharma, Abhishek
• Is Part Of: Chemical science. Volume 12:Issue 22(2021)
• Page Start: 7924
• Page End: 7929
• Publication Date: 2021-05-11
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d1sc00905b
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : A novel C3 acylboron building block; acrylic boronate has been developed and its versatility for synthesis of several previously inaccessible organoborons and heterobifunctional ligations is described. 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.