A Highly Selective Nucleophilic and Radical Relay Difluorination of Cyclopropanes and Alkenes
Abstract
Abstract Fluoro‐containing organic compounds have been found wide application in pharmaceutical and agrochemical industries and in medical diagnostics. In this field, the construction of C─F bonds through nucleophilic fluorination strategies remains highly challenging. Herein, we have developed a radical‐polar strategy for visible‐light‐induced nucleophilic fluorination and subsequent radical fluorination, allowing for direct difluorination of cyclopropanes and styrenes under mild reaction conditions. It affords a series of structurally diverse, both 1,3‐ and 1,2‐difluorinated products in synthetically useful yields by means of ∼0.1 mol% of 4CzIPN as catalyst. Furthermore, only 3 equivalents of Et 3 N·3HF are required to realize an efficient nucleophilic fluorination, while 1.7 equivalents of Selectfluor are used as the radical fluorinating source, demonstrating good functional group compatibility and thus can be applied in late‐stage difluorination of complex molecules.
Article Details
Authors (10)
Junheng Liu
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 Nanjing 210023 China
Haonan Bai
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 Nanjing 210023 China
Zhehan Liang
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 Nanjing 210023 China
Yuxi Gao
Weipeng Li
State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing Drum Tower Hospital, Jiangsu Key Laboratory of Advanced Organic Materials, Chemistry and Biomedicine Innovation Center (ChemBIC)
Li‐Qu Huang
Children's Hospital of Nanjing Medical University Nanjing 210008 China
Tao Zhong
Institute of Fundamental and Frontier Sciences
Guichao Dong
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 Nanjing 210023 China
Chengjian Zhu
State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing Drum Tower Hospital, Jiangsu Key Laboratory of Advanced Organic Materials, Chemistry and Biomedicine Innovation Center (ChemBIC)
Jin Xie