Magnesium-Catalyzed Hydroboration of Terminal and Internal Alkynes

Marc Magre; Bholanath Maity; Alban Falconnet; Luigi Cavallo; Magnus Rueping

doi:10.1002/anie.201902188

Magnesium-Catalyzed Hydroboration of Terminal and Internal Alkynes

Angew Chem Int Ed Engl. 2019 May 20;58(21):7025-7029. doi: 10.1002/anie.201902188. Epub 2019 Apr 12.

Authors

Marc Magre¹, Bholanath Maity², Alban Falconnet¹, Luigi Cavallo², Magnus Rueping^{1

2}

Affiliations

¹ Institute of Organic Chemistry, RWTH Aachen, Landoltweg 1, 52074, Aachen, Germany.
² KAUST Catalysis Center (KCC), King Abdullah University of Science and Technology (KAUST), Thuwal, 23955-6900, Saudi Arabia.

PMID: 30977970
DOI: 10.1002/anie.201902188

Abstract

A magnesium-catalyzed hydroboration of alkynes providing good yields and selectivities for a wide range of terminal and symmetrical and unsymmetrical internal alkynes has been developed. The compatibility with many functional groups makes this magnesium catalyzed procedure attractive for late stage functionalization. Experimental mechanistic investigations and DFT calculations reveal insights into the reaction mechanism of the magnesium catalyzed protocol.

Keywords: DFT; alkynes; hydroboration; magnesium; vinyl borane.