Visible‐Light‐Irradiated Multicomponent Reactions of Aliphatic Amines, Propiolate Acid Esters, and CF3SO2Na for Accessing β‐CF3 Enamines

Author:

Tang Yisong1,Huang Mingyang1,Jiang Liang1,Zhang Xiaotong1,Zheng Shaojun1,Yang Yong2,Chen Xiao Yun1ORCID

Affiliation:

1. School of Environmental and Chemical Engineering Jiangsu University of Science and Technology Zhenjiang 212003 P. R. China

2. College of Mechanical Engineering Suzhou University of Science and Technology Suzhou 320500 P. R. China

Abstract

AbstractA novel one‐pot two‐step multicomponent reaction has been achieved for the preparation of β‐CF3 enamines by using different aliphatic amines, propiolates, and CF3SO2Na as starting material. In this protocol, various aliphatic amines including primary amines, cyclic or acyclic secondary amines were demonstrated to be good coupling partners, and different β‐CF3 enamines were obtained in moderate to good yields. Among them, the primary aliphatic amines only gave pure (E)‐β‐CF3 enamines as products. The synthetic utility of the MCRs strategy was further demonstrated by mild conditions, gram‐scale synthesis and natural sunlight‐induced protocol. Preliminary mechanistic studies suggest that this trifluoromethylation of C(sp2)−H involves radical process.

Funder

National Natural Science Foundation of China

Publisher

Wiley

Subject

General Chemistry,Catalysis,Organic Chemistry

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