Visible light-driven photocatalytic thiol-ene/yne reactions using anisotropic 1D Bi2S3 nanorods: a green synthetic approach.

Abstract

Thiol-ene/yne click reactions play a significant role in creating carbon-sulfur (C-S) bonds, and there has been a growing interest in using visible-light photoredox catalysis for their formation. In this study, anisotropic 1D Bi2S3 nanorods were prepared using a simple polyol-assisted reflux method, and they were used as catalysts for the thiol-ene/yne click reactions under visible light irradiation. The developed protocol is highly compatible and tolerant to various substrates with excellent product yields. Also, thiol-ene and -yne reactions achieved maximum TONs of 93 and 95, respectively. Detailed mechanistic studies were conducted and supported by NMR studies, radical trapping utilizing TEMPO, and ESI-MS product analysis. The ability of Bi2S3 nanorods to catalyze thiol-ene/yne reactions is primarily due to the creation of photoexcited holes, which aid in the formation of thiyl radicals. This method can be scaled up to the gram-scale synthesis of benzyl styryl sulfide with an excellent chemical yield of 90%. The 1D Bi2S3 nanorods also demonstrated structural and morphological stability throughout five reaction cycles while maintaining a favorable photocatalytic activity. The developed methodology had the advantages of broad substrate scope, mild reaction conditions, scaled-up synthesis, and nonrequirement of free radical initiators.