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Synthesis of Trifluoromethanesulfanylbenzofulvenes via a Cascade Electrophilic Cyclization under Mild Conditions
Author(s) -
Xiao Qing,
Zhu Hui,
Li Guangming,
Chen Zhiyuan
Publication year - 2014
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.201400561
Subject(s) - chemistry , electrophile , moiety , nucleophile , combinatorial chemistry , thio , ring (chemistry) , cascade , chloride , trifluoromethyl , organic chemistry , medicinal chemistry , catalysis , alkyl , chromatography
The introduction of the (trifluoromethyl)thio moiety into organic molecules has aroused comprehensive interest recently. We describe herein an efficient and chemoselective synthesis of trifluoromethanesulfanylbenzofulvenes through BiCl 3 ‐ or TsOH‐promoted cascade electrophilic cyclization reactions. The presence of the trifluoromethanesulfanyl cation (CF 3 S + ) would facilitate the electrophilic ring closure and nucleophilic attack of chloride or TsOH. This reaction provides a concise method for the synthesis of chlorine‐ or tosyloxy‐substituted trifluoromethanesulfanylbenzofulvenes in good to excellent yields.