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Facile one-pot synthesis of diarylacetylenes from arylaldehydes via an addition-double elimination process†
Jianyang Chen,Xuan Zhang,Jiajun Wu,Rui Wang,Chunlin Lei,Yanan An
Organic & Biomolecular Chemistry Pub Date : 05/04/2021 00:00:00 , DOI:10.1039/D1OB00627D
Abstract

A practical one-pot protocol has been developed to synthesize diarylacetylenes from arylaldehydes by treatment with 1-(arylmethyl)benzotriazoles and LiN(SiMe3)2. The reaction proceeded through imine formation, Mannich-type addition and double elimination to deliver products in up to 99% yields with broad substrate scope. In addition, gram-scale synthesis of 1-bromo-4-(phenylethynyl)benzene has been demonstrated.

Graphical abstract: Facile one-pot synthesis of diarylacetylenes from arylaldehydes via an addition-double elimination process
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