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Copper(I)-Catalyzed Formal Carboboration of Alkynes: Synthesis of Tri- and Tetrasubstituted Vinylboronates

Ricardo Alfaro, Alejandro Parra, José Alemán, José Luis García Ruano and Mariola Tortosa*

*Departamento de Química Orgánica (módulo 01), Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain, Email: mariola.tortosauam.es

R. Alfaro, A. Parra, J. Alemán, J. L. G. Ruano, M. Tortosa, J. Am. Chem. Soc., 2012, 134, 15165-15168.

DOI: 10.1021/ja307670k (free Supporting Information)


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Abstract

In a copper-catalyzed formal carboboration of alkynes, a C-B bond and a C-C bond are created in a single catalytic cycle. The reaction proceeds with high regioselectivity and syn-stereoselectivity to form tri- and tetrasubstituted vinylboronic esters from commercially available bis(pinacolato)diboron. A subsequent cross-coupling reaction gives access to highly substituted alkenes.

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Key Words

Alkylation of Alkenes, Borylation


ID: J48-Y2012-2970