Transfer Hydrogenation vs Nucleophilic Addition: Aryne Reaction with Alcohols

Abstract

CommentaryMOJ Biorg Org Chem 2017, 1(1): 00004 manner [7]. As an illustrative example, when carbodiimide, a not well recognized nucleophile, and methanol are both present, aryne would selectively react with the former [8]. This seemingly counterintuitive "inertness" of benzyne toward aliphatic alcohols, along with some others highlighted in our recent review [9], constitutes a long-standing curiosity for aryne chemists, both synthetically and mechanistically.