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Silver‐Assisted Difunctionalization of Terminal Alkynes: Highly Regio‐ and Stereoselective Synthesis of Bromofluoroalkenes
Author(s) -
Li Yibiao,
Liu Xiaohang,
Ma Deyun,
Liu Bifu,
Jiang Huanfeng
Publication year - 2012
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201200250
Subject(s) - chemistry , regioselectivity , moiety , reagent , halogen , halide , reactivity (psychology) , stereoselectivity , halogenation , fluoride , triple bond , combinatorial chemistry , organic chemistry , medicinal chemistry , double bond , catalysis , inorganic chemistry , alkyl , medicine , alternative medicine , pathology
The difunctionalization of terminal alkynes was achieved with silver fluoride (AgF) and N ‐bromosuccinimide (NBS) as halogen sources. The presence of the halide moiety greatly enhances the reactivity of the vinyl fluoride compounds that can probably can be transformed into various products that are difficult or even impossible to obtain via direct fluorination. Meanwhile, the monofluoro<.>alkenes were facilely synthesized via a highly chemo‐ and regioselective fluorination of electron‐deficient CC triple bonds using AgF as fluorinating reagent in good yields.