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Simple sulfinate synthesis enables C-H trifluoromethylcyclopropanation.

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.

SUBMITTER: Gianatassio R

PROVIDER: S-EPMC4186797 | biostudies-literature | 2014 Sep

REPOSITORIES: biostudies-literature

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Simple sulfinate synthesis enables C-H trifluoromethylcyclopropanation.

Gianatassio Ryan R Kawamura Shuhei S Eprile Cecil L CL Foo Klement K Ge Jason J Burns Aaron C AC Collins Michael R MR Baran Phil S PS

Angewandte Chemie (International ed. in English) 20140803 37

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. ...[more]

PMID: 25088979

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