Synthesis of Functionalized Cyclopropanes from Carboxylic Acids via a Radical Addition-Polar Cyclization Cascade

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Abstract

Herein, we describe the development of a photoredox‐catalyzed decarboxylative radical addition–polar cyclization cascade approach to functionalized cyclopropanes. Reductive termination of radical–polar crossover reactions between aliphatic carboxylic acids and electron‐deficient alkenes yielded carbanion intermediates that were intercepted in intramolecular alkylations with alkyl chlorides appended to the alkene substrate. The mild conditions, which make use of a readily available organic photocatalyst and visible light, were demonstrated to be amenable to a broad range of structurally complex carboxylic acids and a wide variety of chloroalkyl alkenes, demonstrating exquisite functional group tolerance.
Original languageEnglish
Pages (from-to)15430-15434
Number of pages6
JournalAngewandte Chemie - International Edition
Volume57
Issue number47
Early online date25 Oct 2018
DOIs
Publication statusPublished - 19 Nov 2018

Keywords

  • photoredox catalysis
  • Cyclopropanes
  • carboxylic acids
  • radical-polar crossover
  • decarboxylation

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