Borylation of Propargylic Substrates by Bimetallic Catalysis. Synthesis of Allenyl, Propargylic, and Butadienyl Bpin Derivatives

Tony S. N. Zhao, Yuzhu Yang, Timo Lessing and Kálmán J. Szabó*

*Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, SE-10691 Stockholm, Sweden, Email: kalmanorgan.su.se

T. S. N. Zhao, Y. Yang, T. Lessing, K. J. Szabo, J. Am. Chem. Soc., 2014, 136, 7359-7542.

DOI: 10.1021/ja502792s

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Abstract

Bimetallic Pd/Cu and Pd/Ag catalytic systems enable a stererospecifically borylation of propargylic alcohol derivatives via formal S_N2′ pathways to give allenyl boronates. Opening of propargyl epoxides leads to 1,2-diborylated butadienes probably via en allenylboronate intermediate.

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Key Words

Allenes, Boronates

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ID: J48-Y2014