Synthesis of m-Terphenyl Derivatives via Domino Diels–Alder/Retro-Diels–Alder Reaction of 1,3-Dienic δ-Sultones with Alkynes

Dedicated to Dr. Margit Gruner on the occasion of her 65^th birthday

Abstract

A highly regioselective synthetic method based on the domino Diels–Alder/retro-Diels–Alder reaction (DA/RDA) of 1,3-dienic δ-sultones with alkynes provides substituted m-terphenyls by elimination of SO₃. A variety of δ-sultones and alkynes were examined to determine the scope of the reaction. The de novo synthesized aromatic products were obtained using thermal, microwave, and high-pressure activation.

Key words

m-terphenyls - sultones - Diels–Alder reaction - alkynes - high pressure

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