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

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.

SUBMITTER: Al-Huniti MH

PROVIDER: S-EPMC6179452 | biostudies-literature | 2018 Oct

REPOSITORIES: biostudies-literature

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

Al-Huniti Mohammed H MH Rivera-Chávez José J Colón Katsuya L KL Stanley Jarrod L JL Burdette Joanna E JE Pearce Cedric J CJ Oberlies Nicholas H NH Croatt Mitchell P MP

Organic letters 20180917 19

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 ...[more]

PMID: 30221526

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