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Research Article Open access CC BY 4.0

The Regio- and Stereoselective Synthesis of 1,4-Diarylbut-1-en-3-ynes Having Aryl Groups at the Mutual Syn Positions

Szymon Rogalski, Natalia Szymaszek, Cezary Pietraszuk

Organics · pp. 206–218 · Published 8 May 2023

10.3390/org4020017

Abstract

(E)-1-aryl-2,4-bis(trimethylsilyl)but-1-en-3-ynes readily undergo protodesilylation and subsequent aerobic, copper-free Sonogashira cross-coupling with aryl halides to form (E)-1,4-diaryl-2-(trimethylsilyl)but-1-en-3-ynes. The proposed one-pot, two-step approach allows access to the isomers containing aryl substituents in mutual syn positions. The resulting 2-silyl enynes can be further converted by proto- or halodesilylation.

Aryl Trimethylsilyl Stereoselectivity Sonogashira coupling Chemistry Silylation Halide Stereochemistry

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