A simple method to convert readily available carboxylic acids into sulfinate salts 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.
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.
Sulfinates are readily available from carboxylic acids using classic Barton chemistry. The sulfinates are used to functionalize a diverse range of heterocycles of potential interest in medicinal chemistry. -(GIANATASSIO, R.; KAWAMURA, S.; EPRILE, C. L.; FOO, K.; GE, J.; BURNS, A. C.; COLLINS, M. R.; BARAN*, P. S.; Angew. Chem., Int. Ed. 53 (2014) 37, 9851-9855, http://dx.
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