Pd-Catalyzed One-Pot Dehydroxylative Coupling of Phenols and Amines under a Carbon Monoxide Atmosphere: A Chemical-Specific Discrimination for Arylcarboxylic Amide Synthesis

A simple one-pot process for the synthesis of amides through Pd-catalyzed dehydroxylative coupling of phenols and amines with the insertion of carbon monoxide was developed. This protocol afforded exclusive chemical selectivity for accessing arylcarboxylic amides from phenols by using acyclic amines...

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Bibliographic Details
Published inAsian journal of organic chemistry Vol. 7; no. 4; pp. 751 - 756
Main Authors Fang, Wan-Yin, Huang, Yu-Mei, Leng, Jing, Qin, Hua-Li
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 01.04.2018
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
phenols
PEPTIDES
sulfuryl fluoride
CARBONYLATION REACTIONS
arylcarboxylic amides
aryl fluorosulfonates
sulfonamides
BOND
CARBOXYLIC-ACIDS
FLUORIDE
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Summary:A simple one-pot process for the synthesis of amides through Pd-catalyzed dehydroxylative coupling of phenols and amines with the insertion of carbon monoxide was developed. This protocol afforded exclusive chemical selectivity for accessing arylcarboxylic amides from phenols by using acyclic amines. The same reaction provided sulfonamides if cyclic amines were used. The reaction proceeds smoothly under mild conditions and tolerates a variety of functional groups. The versatility of this method represents an alternative to the known processes for the preparation of amides.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.201800037