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: kanai
mol.f.u-tokyo.ac.jp
T. Itoh, Y. Shimizu, M. Kanai, J. Am. Chem. Soc., 2016, 138, 7528-7531.
DOI: 10.1021/jacs.6b04646
see article for more reactions
Abstract
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.
see article for more examples
Key Words
alkenes, vinylboronates, multicomponent reactions
ID: J48-Y2016
