Photochemical halogen-bonding assisted carbothiophosphorylation reactions of alkenyl and 1,3-dienyl bromides
Literature Information
Publication Date
2023-10-30
DOI
10.1039/D3SC05263J
Impact Factor
9.825
Authors
Helena F. Piedra, Victoria Gebler, Carlos Valdés, Manuel Plaza
View Original
Abstract
Herein, we present a synthetic procedure for the facile and general preparation of novel S-alkenyl and dienyl phosphoro(di)thioates for the first time. Extensive mechanistic investigations support that the reactions rely on a photochemical excitation of a halogen-bonding complex, formed with a phosphorothioate salt and an alkenyl or dienyl bromide, which light-induced fragmentation leads to the formation of the desired products through a radical-based pathway. The substrate scope is broad and exhibits a wide functional group tolerance in the formation of the final compounds, including molecules derived from natural products, all with unknown and potentially interesting biological properties. Eventually, a very efficient continuous flow protocol was developed for the upscale of these reactions.
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Chemical Science
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