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Synthesis of α-aminoketones from N-sulfonyl-1,2,3-triazoles via N-sulfinyl imines generated by intramolecular oxygen transfer
Literature Information
Publication Date
2019-03-05
DOI
10.1039/C9QO00126C
Impact Factor
5.281
Authors
Ze-Feng Xu, Lihong Shan, Wan Zhang, Mengjie Cen, Chuan-Ying Li
View Original
Abstract
A general procedure for intramolecular oxygen transfer from sulfonyl to a carbenoid carbon was established, extending the reaction mode of the corresponding common N-sulfonyl-1,2,3-triazoles. Indoles, and some other arenes, were employed as nucleophiles to react with the resulting key N-sulfinyl imine intermediate, and valuable α-aminoketones could be synthesized conveniently. The synthetic utility of the products was further exhibited by convenient synthesis of gem-diaryl ketones and densely substituted pyrrole. A tentative reaction mechanism was proposed according to control experiments.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
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