title: Facile synthesis of 2-arylmethylindoles and 2-vinylic indoles through palladium-catalyzed heteroannulations of 2-(2-propynyl)aniline and 2-(2-propynyl)tosylanilide.
abstract: A facile method for the general synthesis of 2-arylmethylindoles has been developed through the reaction of 2-(2-propynyl)aniline or 2-(2-propynyl)tosylanilide with aryl iodides in the presence of Pd(OAc)2, PPh3, and DBU. 2-(2-Propynyl)tosylanilide is found to be reactive also towards electron deficient alkenes in the presence of Pd(OAc)2 and sodium iodide under an oxygen atmosphere, providing easy access to 2-vinylic indoles which possess exclusive E-stereochemistry in the side chain double bond. Operational simplicity, compatibility of the various functional groups, and ease of product formation are the hallmarks of these methods. A mechanism has been proposed to explain the product formation.
authors.affiliation: Chemistry Division, Indian Institute of Chemical Biology (CSIR), 4, Raja S. C. Mullick Road, Kolkata-700032, India. chinmay@iicb.res.in.
authors.forename: Bimolendu
authors.initials: B
authors.lastname: Das
authors.forename: Priyanka
authors.initials: P
authors.lastname: Kundu
authors.forename: Chinmay
authors.initials: C
authors.lastname: Chowdhury
mesh_terms: D000813:Anilides / Q000737:chemistry*; D000814:Aniline Compounds / Q000737:chemistry*; D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C000592073:2-(2-propynyl)aniline; C000592074:2-(2-propynyl)tosylanilide; D000813:Anilides; D000814:Aniline Compounds; D007211:Indoles; D010165:Palladium