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Shu C, Mega RS, Andreassen BJ, et al. Synthesis of Functionalized Cyclopropanes from Carboxylic Acids by a Radical Addition-Polar Cyclization Cascade. Angew Chem Int Ed Engl. 2018;57(47):15430-15434doi: 10.1002/anie.201808598.
Shu, C., Mega, R. S., Andreassen, B. J., Noble, A., & Aggarwal, V. K. (2018). Synthesis of Functionalized Cyclopropanes from Carboxylic Acids by a Radical Addition-Polar Cyclization Cascade. Angewandte Chemie (International ed. in English), 57(47), 15430-15434. https://doi.org/10.1002/anie.201808598
Shu, Chao, et al. "Synthesis of Functionalized Cyclopropanes from Carboxylic Acids by a Radical Addition-Polar Cyclization Cascade." Angewandte Chemie (International ed. in English) vol. 57,47 (2018): 15430-15434. doi: https://doi.org/10.1002/anie.201808598
Shu C, Mega RS, Andreassen BJ, Noble A, Aggarwal VK. Synthesis of Functionalized Cyclopropanes from Carboxylic Acids by a Radical Addition-Polar Cyclization Cascade. Angew Chem Int Ed Engl. 2018 Nov 19;57(47):15430-15434. doi: 10.1002/anie.201808598. Epub 2018 Oct 25. PMID: 30204292; PMCID: PMC6282618.
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Angew Chem Int Ed Engl. 2018 Nov 19;57(47):15430-15434. doi: 10.1002/anie.201808598. Epub 2018 Oct 25.

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

Angewandte Chemie (International ed. in English)

Chao Shu, Riccardo S Mega, Björn J Andreassen, Adam Noble, Varinder K Aggarwal

Affiliations

  1. School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.

PMID: 30204292 PMCID: PMC6282618 DOI: 10.1002/anie.201808598

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.

© 2018 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.

Keywords: carboxylic acids; cyclopropanes; decarboxylation; photoredox catalysis; radical-polar crossover

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