Computational predictions of substituted benzyne and indolyne regioselectivities

A computational study using DFT methods was performed for an array of mono and disubstituted benzynes and indolynes. The inherent distortion present in the geometry-optimized structures gives a prediction of the regioselectivity of aryne trapping by nucleophiles or cycloaddition partners. These studies will serve to enable the further use of unsymmetrical arynes in organic synthesis. (C) 2015 Elsevier Ltd. All rights reserved.