Alkaline-Earth-Catalyzed Dehydrocoupling of Amines and Boranes

David J Liptrot; Michael S Hill; Mary F Mahon; Andrew S S Wilson

doi:10.1002/anie.201505949

Alkaline-Earth-Catalyzed Dehydrocoupling of Amines and Boranes

Angew Chem Int Ed Engl. 2015 Nov 2;54(45):13362-5. doi: 10.1002/anie.201505949. Epub 2015 Sep 11.

Authors

David J Liptrot¹, Michael S Hill², Mary F Mahon¹, Andrew S S Wilson¹

Affiliations

¹ Department of Chemistry, University of Bath, Bath BA2 7AY (UK).
² Department of Chemistry, University of Bath, Bath BA2 7AY (UK). msh27@bath.ac.uk.

Abstract

Dehydrocoupling reactions between the boranes HBpin and 9-borabicyclo[3.3.1]nonane and a range of amines and anilines ensue under very mild reaction conditions in the presence of a simple β-diketiminato magnesium n-butyl precatalyst. The facility of the reactions is suggested to be a function of the Lewis acidity of the borane substrate, and is dictated by resultant pre-equilibria between, and the relative stability of, magnesium hydride and borohydride intermediates during the course of the catalysis.

Keywords: BN coupling; alkaline-earth metals; amines; boron; magnesium.

© 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.