Abstract

A variant of a classical reaction has been used to generate short-lived chemical species called arynes, allowing the one-step synthesis of structurally complex benzene derivatives from simple precursors. See Article p.208 Arynes are reactive intermediates derived from aromatic systems, which can be 'trapped' to give products that find use as chemical reagents and in pharmaceuticals, agrochemicals, dyes and polymers. This study explores a new synthetic strategy that combines de novo generation of benzynes — through a hexadehydro-Diels–Alder reaction — with their in situ elaboration into structurally complex benzenoid products. The reaction is metal-free and reagent-free, and the authors provide examples of how this approach allows new modes of intrinsic reactivity to be revealed.

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