Sulfur Heterocyclization and 1,3-Migration of Silicon in Reaction of 1,3-Diynes with Sodium Triisopropylsilanethiolate: One-Pot Synthesis of 2,5-Disubstituted 3-(Triisopropylsilyl)thiophenes

Abstract

Sulfur heterocyclization and 1,3-migration of silicon have been realized in the reactions of a range of 1,3-diynes with sodium triisopropylsilanethiolate in N,N-dimethylformamide. These provided 40–72% yields of 2,5-disubstituted 3-(triisopropylsilyl)thiophenes and up to 50% yield of 2,5-disubstituted thiophenes.

Key words

1,3-diynes - cyclizations - 1,3-migration of silicon - thiophene - sulfur heterocycles

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