Synthesis 2015; 47(15): 2242-2248
DOI: 10.1055/s-0034-1380524
special topic
© Georg Thieme Verlag Stuttgart · New York

Copper(II)-Catalyzed β-Borylation of Acetylenic Esters in Water

Cheryl L. Peck
Department of Chemistry, Virginia Tech, Blacksburg, VA 24061, USA   Email: santosw@vt.edu
,
Joseph A. Calderone
Department of Chemistry, Virginia Tech, Blacksburg, VA 24061, USA   Email: santosw@vt.edu
,
Webster L. Santos*
Department of Chemistry, Virginia Tech, Blacksburg, VA 24061, USA   Email: santosw@vt.edu
› Author Affiliations
Further Information

Publication History

Received: 09 March 2015

Accepted: 12 March 2015

Publication Date:
23 April 2015 (online)

Abstract

A method for the β-borylation of alkynoates has been developed. In the presence of bis(pinacolato)diboron and catalytic amounts of both copper(II) and 4-picoline, substituted alkynoates undergo borylation in a regio-, stereo-, and chemoselective fashion. The reaction is performed under mild conditions using water as solvent and open to the atmosphere to exclusively afford (Z)-β-boryl-α,β-unsaturated esters.

Supporting Information

 
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