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Ligand-Enabled, Copper-Catalyzed Regio- and Stereoselective Synthesis of Trialkylsubstituted Alkenylboronates from Unactivated Internal Alkynes

Taisuke Itoh, Yohei Shimizu and Motomu Kanai*

*Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan, Email:

T. Itoh, Y. Shimizu, M. Kanai, J. Am. Chem. Soc., 2016, 138, 7528-7531.

DOI: 10.1021/jacs.6b04646

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In a copper-catalyzed regio- and stereoselective borylalkylation of dialkylsubstituted internal alkynes with bis(pinacolato)diboron and alkyl halides, a borylcopper species containing a novel π-accepting N-heterocyclic carbene ligand chemoselectively reacted with unactivated internal alkynes over alkyl halides. The intermediate alkenylcopper species subsequently reacted with alkyl halides, affording the desired products.

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Key Words

alkenes, vinylboronates, multicomponent reactions

ID: J48-Y2016