Ceri-ously Simple

Ceri-ously Simple

Author: Richard Threlfall

Amides are known as the least reactive class of carbonyl compounds. Their unreactive nature is sometimes useful; however, anyone who has tried to convert an amide into a different and more synthetically versatile functional group will know the frustrations encountered.

A solution to this problem is now at hand courtesy of Pei-Qiang Huang and co-workers, Xiamen University, China. Their general procedure for directly transforming secondary amides into ketones in one pot involves combining the amide with 2-fluoropyridine and trifluoromethanesulfonic anhydride to activate the carbonyl group, and then subsequent treatment with an organometallic reagent, cerium chloride, and an acid completes the deaminative alkylation. The reaction tolerates a wide range of functional groups on the substrates, and the team hopes to extend the method to produce secondary amines and ketimines from the same starting materials.

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