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A facile route to 3-sulfonylated and 3-(1-benzotriazolyl)-benzofurans is achieved from readily available o -hydroxyphenyl propargyl alcohols ( o -HPPAs) and bench-top sodium sulfonylates and benzotriazoles with no assistance of any reagent or catalyst. Bifunctional o -quinone methides ( o -QMs) were the putative reaction intermediates ensued from dehydration of o -HPPA. Our study revealed that the o -QM was so choosy in selection of the nucleophiles for the key Michael addition reaction.

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3-Heterosubstituted Benzofurans from Hydroxyphenyl Propargyl Alcohols via <i>ortho</i>-Quinone Methide through a Metal-/Catalyst-Free Conjugate Addition/Oxy-Cyclization

3-Heterosubstituted Benzofurans from Hydroxyphenyl Propargyl Alcohols via ortho-Quinone Methide through a Metal-/Catalyst-Free Conjugate Addition/Oxy-Cyclization