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Fluorohalogenation of gem ‐Difluoroalkenes: Synthesis and Applications of α‐Trifluoromethyl Halides
Author(s) -
Liu Chi,
Zhu Chuanle,
Cai Yingying,
Yang Zhiyi,
Zeng Hao,
Chen Fulin,
Jiang Huanfeng
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201905445
Subject(s) - trifluoromethyl , halide , chemistry , nucleophile , electrophile , halogenation , carbanion , fluoride , combinatorial chemistry , trifluoromethylation , organic chemistry , medicinal chemistry , photochemistry , alkyl , catalysis , inorganic chemistry
A novel strategy for 1,2‐dihalogenation of alkenes is reported that occurs through a sequential nucleophilic halide addition and electrophilic halogenation. By trapping the in situ generated unstable α‐trifluoromethyl carbanion intermediates derived from the nucleophilic fluoride addition to electron‐poor gem ‐difluoroalkenes, this fluorohalogenation of gem ‐difluoroalkenes with electrophilic haloalkynes affords various useful α‐trifluoromethyl halides in high yields. A pesticidal active compound and various attractive trifluromethylated molecules could be smoothly synthesized from these obtained α‐trifluoromethyl halides.