Synthesis of Vinyl Sulfides and Vinylamines through Catalytic Intramolecular Hydroarylation in the Presence of FeCl3and AgOTf

Autor: Sunggak Kim, Dahan Eom, Phil Ho Lee, Juntae Mo, Zhiming Gao
Rok vydání: 2012
Předmět:
Zdroj: European Journal of Organic Chemistry. 2013:533-540
ISSN: 1434-193X
DOI: 10.1002/ejoc.201201270
Popis: 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 FeCl3 and AgOTf (OTf = trifluoromethanesulfonate) in 1,2-dichloroethane. A variety of 1,2-dihydronaphthalenes, 2H-chromenes, and 1,2-dihydroquinolines containing a phenylsulfenyl or N-phenyl-N-tosyl group on the sp2-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.
Databáze: OpenAIRE