Simple sulfinate synthesis enables C-H trifluoromethylcyclopropanation

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Abstract

A simple method to convert readily available carboxylic acids into sulfinate salts by employing an interrupted Barton decarboxylation reaction is reported. A medicinally oriented panel of ten new sulfinate reagents was created using this method, including a key trifluoromethylcyclopropanation reagent, TFCS-Na. The reactivity of six of these salts towards C-H functionalization was field-tested using several different classes of heterocycles. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Gianatassio, R., Kawamura, S., Eprile, C. L., Foo, K., Ge, J., Burns, A. C., … Baran, P. S. (2014). Simple sulfinate synthesis enables C-H trifluoromethylcyclopropanation. Angewandte Chemie - International Edition, 53(37), 9851–9855. https://doi.org/10.1002/anie.201406622

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