Factors affecting reactions of trialkylcyanoborates with imidoyl chlorides/trifluoroacetic anhydride

Methods for generating tert-alkyl organoboron species are in high demand as they are invaluable intermediates for the synthesis of quaternary carbon centres. Herein we report investigations into generation of tert-alkyl organoboron species using imidoyl chlorides as reagents in the organoboron cyanidation reaction. Although alkenyl side-products predominate in particularly hindered cases, tert-alkyl organoboron species can be successfully generated for less hindered examples. (C) 2015 Elsevier Ltd. All rights reserved.