Synthesis of β‐Trifluoromethylated Ketones by Photocatalyzed Deoxygenative Coupling of Aromatic Acids with α‐CF3‐Substituted Styrenes

Author:

Zhang Lili1,Yu Xiaoyu1,Ouyang Shenmao1,Zhu Chengjian1,Li Weipeng1,Xie Jin1ORCID

Affiliation:

1. State Key Laboratory of Coordination Chemistry Jiangsu Key Laboratory of Advanced Organic Materials Chemistry and Biomedicine Innovation Center (ChemBIC) School of Chemistry and Chemical Engineering Nanjing University 210023 Nanjing China

Abstract

Abstractα‐Trifluoromethyl alkenes are versatile CF3‐containing feedstocks. They have been widely used to construct gem‐difluoroalkene scaffolds through β−F elimination. The application of α−CF3 alkenes as trifluoromethylating reagents has been less explored. Herein, we report an efficient route for the synthesis of β‐trifluoromethylated ketones from readily accessed α−CF3 styrenes and aromatic carboxylic acids under photoredox catalysis. The reactions proceed by phosphoranyl radical promoted deoxygenation of aromatic acids, generating acyl radicals for subsequent hydroacylation of α−CF3 styrenes. The valuable trifluoromethyl‐containing compounds could be produced in good yields under mild conditions.

Funder

National Natural Science Foundation of China

National Key Research and Development Program of China

Fundamental Research Funds for the Central Universities

Publisher

Wiley

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