Amidation of β-Keto Sulfonyl Fluorides via C-C Bond Cleavage

A simple protocol for amide bond construction using beta-keto sulfonyl fluorides (BKSFs) as the acyl surrogates has been achieved. The reaction of BKSFs with a range of amines could be performed in presence of N-bromosuccinimide (NBS), affording various amides with diverse functionalities. Preliminary mechanistic studies revealed that the dibromo-substituted sulfonyl fluorides could be the key intermediate in this amidation process. A simple protocol has been developed for amide bond construction using beta-keto sulfonyl fluorides as the acyl surrogates. These readily available BKSFs can be reacted with a variety of amines in presence of N-bromosuccinimide, producing the desired amides with diverse functionalities. image