Photochemical halogen-bonding assisted carbothiophosphorylation reactions of alkenyl and 1,3-dienyl bromides

文献情報

出版日 2023-10-30

DOI 10.1039/D3SC05263J

インパクトファクター 9.825

著者

Helena F. Piedra, Victoria Gebler, Carlos Valdés, Manuel Plaza

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要旨

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.

掲載誌

Chemical Science

CiteScore: 14.4

自己引用率: 3.9%

年間論文数: 1413

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Photochemical halogen-bonding assisted carbothiophosphorylation reactions of alkenyl and 1,3-dienyl bromides

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