Synthesis of isochromanes and isothiochromanes bearing fluorinated one-carbon units via intramolecular cyclizations of ortho-substituted α-(trifluoromethyl) styrenes

J Ichikawa, M Ikeda, M Hattori

Index: Ichikawa, Junji; Ikeda, Masahiro; Hattori, Masahiro Heterocycles, 2009 , vol. 77, # 2 p. 1285 - 1296

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Citation Number: 5

Abstract

抄録 α-(Trifluoromethyl) styrenes bearing a nucleophilic oxygen or sulfur atom tethered by a methylene or methyne unit at the ortho carbon were prepared by the coupling reaction of 2- bromo-3, 3, 3-trifluoropropene with aryl iodides via (3, 3, 3-trifluoroprop-1-en-2-yl) boronic acid. The styrenes thus obtained readily undergo an intramolecular nucleophilic addition or substitution (SN2'-type) of the oxygen and sulfur under basic conditions, leading to 4- ...