Site-specific preparation of 3-fluoro-1-substituted-naphthalenes via a novel base-catalyzed cyclization reaction from (E)-monofluoroenynes.
A novel cyclization reaction for the preparation of 3-fluoro-1-substituted-naphthalenes is reported. (E)-Monofluoroenynes, which are prepared by Sonogashira coupling reaction from (Z)-1-bromo-1-fluoroalkenes, undergo cyclization to afford 3-fluoro-1-substituted-naphthalenes in good to excellent yields when treated with DABCO or DBU in refluxing N-methyl-2-pyrrolidinone (NMP). [reaction: see text]
Xu
Jianjun
J
Department of Chemistry, University of Iowa, Iowa City, IA 52242, USA.
Wang
Yi
Y
Burton
Donald J
DJ