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Synthesis of Vinyl Sulfides and Vinylamines through Catalytic Intramolecular Hydroarylation in the Presence of FeCl 3 and AgOTf
Author(s) -
Eom Dahan,
Mo Juntae,
Lee Phil Ho,
Gao Zhiming,
Kim Sunggak
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201270
Subject(s) - chemistry , intramolecular force , catalysis , trifluoromethanesulfonate , medicinal chemistry , tosyl , organic chemistry , polymer chemistry
A synthetic method was developed for the preparation of vinyl sulfides and vinylamines from arylalkynyl phenyl sulfides and sulfonamides. Under mild conditions, a catalytic intramolecular hydroarylation reaction was carried out in the presence of FeCl 3 and AgOTf (OTf = trifluoromethanesulfonate) in 1,2‐dichloroethane. A variety of 1,2‐dihydronaphthalenes, 2 H ‐chromenes, and 1,2‐dihydroquinolines containing a phenylsulfenyl or N ‐phenyl‐ N ‐tosyl group on the sp 2 ‐hybridized benzylic carbon were prepared in good to excellent yields. The present method could be extended to the preparation of dihydropyrano[2,3‐ g ]chromenes through a twofold Fe‐catalyzed hydroarylation by a selective 6‐ endo mode.