Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 47, Pages 15430-15434Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201808598
Keywords
carboxylic acids; cyclopropanes; decarboxylation; photoredox catalysis; radical-polar crossover
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Funding
- EPSRC [EP/I038071/1]
- H2020 ERC [670668]
- BBSRC [BB/F011539/1] Funding Source: UKRI
- EPSRC [EP/K03927X/1, EP/L011999/1, EP/I038071/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/K03927X/1] Funding Source: researchfish
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Herein, we describe the development of a photo-redox-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.
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