Synthesis of vinyl sulfides and vinylamines through catalytic intramolecular hydroarylation in the presence of FeCl3 and AgOTf

• Main Authors: Eom, Dahan., Mo, Juntae., Lee, Phil Ho., Gao, Zhiming., Kim, Sunggak.
• Other Authors: School of Physical and Mathematical Sciences
• Format: Article
• Language: English
• Published: 2013
• Subjects: DRNTU::Science::Chemistry::Organic chemistry
• Online Access: https://hdl.handle.net/10356/99757; http://hdl.handle.net/10220/17643
• Institution: Nanyang Technological University

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.