Benzannulated Bicycles by Three-Component Aryne Reactions

摘要

Benzyne has been an integral tool for the discovery of new multicomponent reactions for over 70 years. In particular, the ability to function as a relay species between a nucleophile and an electrophile makes this reactive intermediate well suited to the rapid preparation of 1,2-disubstituted arene scaffolds. In designing an approach toward new multi-component aryne reactions, we began by considering reactivity patterns of classic transformations. In the Passerini synthesis of α-acyloxyamides (e.g., 6), an aldehyde component (1) acts as both an electrophile and a latent nucleophile (i.e., 1→6) during the course of the reaction (Scheme 1 a).