Development and Utilization of a Palladium-Catalyzed Dehydration of Primary Amides To Form Nitriles

UNCG Author/Contributor (non-UNCG co-authors, if there are any, appear on document)
Mohammed Al-Huniti, Research Scientist (Creator)
Mitchell Croatt, Assistant Professor (Creator)
Nicholas Oberlies, Patricia A. Sullivan Distinguished Professor of Chemistry (Creator)
Cedric J Pearce, Adjunct Professor (Creator)
The University of North Carolina at Greensboro (UNCG )
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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.

Additional Information

Organic Letters 2018, 20, 6046-6050
Language: English
Date: 2018
palladium(II) catalyst, Selectfluor, nitriles, dehydration

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