The preparation of
nitriles from primary amides or aldoximes was
achieved by using oxalyl chloride with a catalytic amount of dimethyl
sulfoxide in the presence of Et3N. The reactions were complete
within 1 h after addition at room temperature. A diverse range of
cyano compounds were obtained in good to excellent yields, including
aromatic, heteroaromatic, cyclic, and acyclic aliphatic species.
The pairing of DMSO and oxalyl bromide is reported as a highly efficient brominating reagent for various alkenes, alkynes and ketones. This bromination approach demonstrates remarkable advantages, such as mild conditions, low cost, short reaction times, provides excellent yields in most cases and represents a very attractive alternative for the preparation of dibromides and α-bromoketones.
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