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Issue 23, 2019
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Metal-free synthesis of gem-silylboronate esters and their Pd(0)-catalyzed cross-coupling with aryliodides

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Abstract

A transition-metal-free method for the synthesis of gem-silylboronate esters with arylboronic acids and trimethylsilyldiazomethane (TMSCHN2) has been developed. This transformation is a straightforward homologation of arylboronic acids and features wide substrate scope and good functional-group tolerance. The gem-silylboronate esters undergo efficient Suzuki–Miyaura cross-coupling with aryliodides and the silyl group of the product can be further functionalized. Tertiary carbon centers with different substituents can be constructed successfully by selective and sequential functionalization.

Graphical abstract: Metal-free synthesis of gem-silylboronate esters and their Pd(0)-catalyzed cross-coupling with aryliodides

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Article information


Submitted
02 May 2019
Accepted
17 May 2019
First published
17 May 2019

Org. Biomol. Chem., 2019,17, 5714-5724
Article type
Paper

Metal-free synthesis of gem-silylboronate esters and their Pd(0)-catalyzed cross-coupling with aryliodides

C. Wu, Z. Bao, X. Xu and J. Wang, Org. Biomol. Chem., 2019, 17, 5714
DOI: 10.1039/C9OB01006H

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