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<p>Decarboxylative functionalization of aliphatic carboxylic acids is a powerful strategy in organic synthesis, yet most methods focus on decarboxylative monofunctionalization. Merging decarboxylation with selective activation of an adjacent C–H bond to deliver vicinal difunctionalization has remained elusive. Here we report an electrophotocatalytic decarboxylative vicinal dichlorination of aliphatic carboxylic acids using 1,2-dichloroethane as both the solvent and the chlorine source. Mechanistic studies indicate the formation of an alkene intermediate via photocatalytic dehydrogenative decarboxyolefination, followed by electrochemical vicinal chlorination. The protocol operates under mild conditions, tolerates diverse functionality and enables late-stage vicinal dichlorination of bioactive molecules and natural products, underscoring its practicality and potential for streamlined synthesis.</p><p></p>

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Electrophotocatalytic decarboxylative vicinal dichlorination of aliphatic carboxylic acids

  • 期刊论文

  • 发表日期：

    2026年5月26日

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  • Kun Cui,
  • Yajuan Li,
  • Shu-Fan He,
  • Guoying Zhang,
  • Daixi Li,
  • Tao Shen

摘要

Decarboxylative functionalization of aliphatic carboxylic acids is a powerful strategy in organic synthesis, yet most methods focus on decarboxylative monofunctionalization. Merging decarboxylation with selective activation of an adjacent C–H bond to deliver vicinal difunctionalization has remained elusive. Here we report an electrophotocatalytic decarboxylative vicinal dichlorination of aliphatic carboxylic acids using 1,2-dichloroethane as both the solvent and the chlorine source. Mechanistic studies indicate the formation of an alkene intermediate via photocatalytic dehydrogenative decarboxyolefination, followed by electrochemical vicinal chlorination. The protocol operates under mild conditions, tolerates diverse functionality and enables late-stage vicinal dichlorination of bioactive molecules and natural products, underscoring its practicality and potential for streamlined synthesis.