Synthesis of Chloro(phenyl)trifluoromethyliodane and Catalyst-Free Electrophilic Trifluoromethylations

• DOI: 10.1021/acs.orglett.8b01510
• Publication Date: 2018-06-20T12:42:30Z
• Authors: Cong Xu; Xiaoning Song; Jia Guo; Sibao Chen; Jie Gao; Jing Jiang; Fengyun Gao; Yuxin Li; Mang Wang
• Keywords: Trifluoromethylation

The present work deals with a challenge in the synthesis of aryltrifluoromethyliodanes (ArICF3X) and develops direct route to PhICF3Cl via simple ligand-exchange reaction PhI(OCOCF3)2, Me3SiCF3, NaCl for first time. I-Cl bond length supports its iodonium character, which enables an enhanced CF3-transfer capability electrophilic S-, O-, N-, C-trifluoromethylations as well catalyst-free trifluoromethylation-cyclizations arylisonitriles.