1-(Dimethoxyphosphoryl)vinyl 4-bromobenzenesulfonate

CAS 3064173-23-2, Cat. No EN300-52481399
Reagent for late-stage homologation

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1-(Dimethoxyphosphoryl)vinyl 4-bromobenzenesulfonate is a novel radical-based reagent for the homologation of carboxylic acids via decarboxylative chain extension¹. This transformation uses redox-active esters (RAEs) derived from carboxylic acids, which undergo a radical-mediated coupling with a vinyl sulfone reagent under photocatalytic conditions. The reaction installs a one-carbon extension into the molecular skeleton, providing a homologated product with excellent functional group tolerance. This method is notable for avoiding traditional homologation strategies such as the Arndt–Eistert reaction and allows late-stage diversification of complex molecules, including pharmaceuticals and natural products. The vinyl sulfone fragment acts as a radical acceptor, offering high stability and compatibility with mild conditions. The process shows excellent selectivity for the carboxylic acid functionality over other potentially reactive groups, including amines and alcohols. Overall, the reagent enables a broadly applicable and modular method for carbon-chain extension in synthetic organic chemistry.

Synonyms: dimethyl 1-[(4-bromobenzenesulfonyl)oxy]ethene-1-phosphonate