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

Cheryl L. Peck, Joseph A. Calderone, Webster L. Santos*

*Department of Chemistry, Virginia Tech, Blacksburg, VA 24061, USA, Email:

C. L. Peck, J. A. Calderone, W. L. Santos, Synthesis, 2015, 47, 2242-2248.

DOI: 10.1055/s-0034-1380524 (free Supporting Information)

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

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Key Words

copper, stereoselectivity, alkynes, vinylboronates

ID: J66-Y2015