title: Palladium-catalyzed approach for the general synthesis of (E)-2-arylmethylidene-N-tosylindolines and (E)-2-arylmethylidene-N-tosyl/nosyltetrahydroquinolines: access to 2-substituted indoles and quinolines.
abstract: A facile and efficient method for the synthesis of (E)-2-arylmethylidene-N-tosylindolines and (E)-2-arylmethylidene-N-tosyl/nosyltetrahydroquinoline variants has been developed through palladium-catalyzed cyclocondensation of aryl iodides with readily available 1-(2-tosylaminophenyl)prop-2-yn-1-ols and their higher homologues, respectively. The proposed reaction mechanism invokes the operation of trans-aminopalladation during cyclization (5/6-exo-dig), which ensures exclusive (E)-stereochemistry in the products. The method is fast, operationally simple, totally regio- and stereoselective, and versatile enough to access a variety of 2-substituted indoles and quinolines. The reactions proceeded efficiently with a wide variety of substrates and afforded the corresponding products in moderate to excellent yields.
authors.affiliation: Chemistry Division, Indian Institute of Chemical Biology (CSIR), 4, Raja S. C. Mullick Road, Jadavpur, Kolkata-700032, India. chinmay@iicb.res.in
authors.forename: Chinmay
authors.initials: C
authors.lastname: Chowdhury
authors.forename: Bimolendu
authors.initials: B
authors.lastname: Das
authors.forename: Sanjukta
authors.initials: S
authors.lastname: Mukherjee
authors.forename: Basudeb
authors.initials: B
authors.lastname: Achari
mesh_terms: D002384:Catalysis; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014105:Tosyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D007211:Indoles; D011804:Quinolines; D014105:Tosyl Compounds; D010165:Palladium