Development and Utilization of a Palladium-Catalyzed Dehydration of Primary Amides To Form Nitriles
Mohammed H Al-Huniti1, José Rivera-Chávez2, Katsuya L Colón1
1Department of Chemistry and Biochemistry , University of North Carolina at Greensboro , 435 Sullivan Science Building , Greensboro , North Carolina 27402 , United States.
Abstract:
A palladium(II) catalyst, in the presence of Selectfluor, enables the efficient and chemoselective transformation of primary amides into nitriles. The amides can be attached to aromatic rings, heteroaromatic rings, or aliphatic side chains, and the reactions tolerate steric bulk and electronic modification. Dehydration of a peptaibol containing three glutamine groups afforded structure-activity relationships for each glutamine residue. Thus, this dehydration can act similarly to an alanine scan for glutamines via synthetic mutation.
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