Copper-catalyzed borylative allyl-allyl coupling reaction

Kazuhiko Semba; Naoto Bessho; Tetsuaki Fujihara; Jun Terao; Yasushi Tsuji

doi:10.1002/anie.201404173

Copper-catalyzed borylative allyl-allyl coupling reaction

Angew Chem Int Ed Engl. 2014 Aug 18;53(34):9007-11. doi: 10.1002/anie.201404173. Epub 2014 Jul 1.

Authors

Kazuhiko Semba¹, Naoto Bessho, Tetsuaki Fujihara, Jun Terao, Yasushi Tsuji

Affiliation

¹ Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510 (Japan) http://twww.ehcc.kyoto-u.ac.jp/; Present Address: Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510 (Japan).

PMID: 24986738
DOI: 10.1002/anie.201404173

Abstract

Borylative allyl-allyl coupling using allenes, bis(pinacolato)diboron, and allyl phosphates has been developed in the presence of a copper catalyst bearing an N-heterocyclic carbene ligand. The reaction affords boryl-substituted 1,5-diene derivatives in good to high yields with high regioselectivity and Z selectivity.

Keywords: CC coupling; allenes; allylic compounds; boron; copper.