Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 37, Pages 9851-9855Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201406622
Keywords
analogue synthesis; bioisosteres; CH functionalization; heterocycles; sulfinate salts
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Funding
- NIH/NIGMS [GM-106210]
- Sigma-Aldrich, Inc.
- Pfizer, Inc.
- Uehara Memorial Foundation
- A*STAR
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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 CH functionalization was field-tested using several different classes of heterocycles.
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