K2CO3-accelerated amidation of carboxylic acids using α-oxo ketene-N, S-acetals as amine surrogates. Issue 3 (20th December 2022)

• Record Type: Journal Article
• Authors: Yu, Haifeng; Zhang, Xue; Li, Liangliang; Luo, Hui; Che, Guangbo
• Is Part Of: Organic chemistry frontiers. Volume 10:Issue 3(2023)
• Page Start: 686
• Page End: 698
• Publication Date: 2022-12-20
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d2qo01716d
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : A novel and efficient K2 CO3 -accelerated amidation of carboxylic acids with α-oxo ketene- N, S -acetals as amine surrogates is developed. Abstract : A novel and efficient K2 CO3 -accelerated amidation of carboxylic acids with α-oxo ketene- N, S -acetals as amine surrogates is developed. The amidation of carboxylic acids is achieved in the presence of 10 mol% of K2 CO3 using readily available ( E )-4-(alkylamino)-4-(ethylthio)but-3-en-2-ones as amine surrogates. The method represents the first example of the synthetic utility of C–N bond cleavage of α-oxo ketene- N, S -acetals. A plausible mechanism is proposed on the basis of the detailed studies, in which the base plays the key role during the transformation.