One-Step Formation both of C-N and of C-O Bonds of N-Alkoxyamides through NHC-Catalyzed Three-Component Reactions of Enals, Nitrosoarenes, and Enones

• Published in: European journal of organic chemistry 2012-09, Vol.2012 (26), p.4982-4987
• Main Authors: Sun, Zhong-Xin, Cheng, Ying
• Format: Article
• Language: English
• Subjects: Carbenes; Cascade reactions; Catalysis; Catalysts: preparations and properties; Chemistry; Domino reactions; Enals; Enones; Exact sciences and technology; General and physical chemistry; Heterocyclic compounds; Multicomponent reactions; Nitrosoarenes; Organic chemistry; Preparations and properties; Synthetic methods; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201200525

NHC‐catalyzed three‐component reactions of α,β‐unsaturated aldehydes (enals), nitrosoarenes, and α,β‐unsaturated ketones (enones) were studied. The reactions proceeded through a cascade aza‐benzoin condensation/oxo‐Michael addition sequence to produce N,O‐bisfunctionalized N‐hydroxylacrylamides in moderate to good yields. This work not only provides an efficient method for the one‐step formation both of the C–N and of the C–O bonds in N‐alkoxyamides, but also advances the application of NHC organocatalysis in the field of multicomponent reactions. NHC‐catalyzed three‐component reactions of α,β‐unsaturated aldehydes (enals), nitrosoarenes, and α,β‐unsaturated ketones (enones) proceeded through a cascade aza‐benzoin condensation/oxo‐Michael addition sequence to produce N,O‐bisfunctionalized N‐hydroxylacrylamides in moderate to good yields.