Organic letters

Synthesis of Primary Amides via Copper-Catalyzed Aerobic Decarboxylative Ammoxidation of Phenylacetic Acids and α-Hydroxyphenylacetic Acids with Ammonia in …

Q Song, Q Feng, K Yang

Index: Song, Qiuling; Feng, Qiang; Yang, Kai Organic Letters, 2014 , vol. 16, # 2 p. 624 - 627

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Citation Number: 34

Abstract

A Cu2O-catalyzed aerobic oxidative decarboxylative ammoxidation to primary benzamides from phenylacetic acids and α-hydroxyphenylacetic acids is developed. A variety of primary benzamides could be prepared smoothly, in good to excellent yields, by means of a one-pot domino protocol combining decarboxylation, dioxygen activation, oxidative C–H bond functionalization, and amidation reactions.

~49%

~56%

~71%

~40%

~57%

~48%

~74%

~44%

~65%

~58%

~63%

~78%

~81%

~63%

~45%

~81%

~70%

~64%

~63%

~36%

~60%

~58%

~51%

~60%

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