Bioinspired Synthesis of Nitriles from Primary Amides via Zinc/Anhydride Catalysis

• Published in: Asian journal of organic chemistry Vol. 7; no. 2; pp. 367 - 370
• Main Authors: Wang, Yuanyuan, Fu, Liyan, Qi, Huimin, Chen, Shu‐Wei, Li, Yuehui
• Format: Journal Article
• Language: English
• Published: Weinheim Wiley Subscription Services, Inc 01-02-2018
• Subjects: Aliphatic compounds; Amides; Amines; Anhydrides; Carboxylic acids; Catalysis; Chemical synthesis; Condensates; cooperative catalysis; Dehydration; hydrosilanes; Nitriles; Organic chemistry; Substrates
• ISSN: 2193-5807; 2193-5815
• DOI: 10.1002/ajoc.201700664

A broad scope of aromatic and aliphatic primary amides were converted to their corresponding nitriles in high yields by using polymethylhydrosiloxane (PMHS) in the presence of catalytic amounts of ZnBr2 and propylphosphonic anhydride (T3P). As an example of dehydration reaction promoted by anhydrides, ZnBr2 and T3P cooperatively activate the amide substrate and the silane to allow the desired dehydration to occur smoothly under mild conditions. Moreover, this method is suitable for the condensation reaction of carboxylic acids with amines to give the corresponding amide products, including a key intermediate of cinacalcet.
Thirsty? You must be dehydrated… As an example of dehydration reaction promoted by anhydrides, primary amides were efficiently converted to the corresponding nitriles by using polymethylhydrosiloxane (PMHS), and catalytic amounts of ZnBr2 and propylphosphonic anhydride (T3P).