title: Catalytic activation of the leaving group in the S(N)2 reaction.
abstract: A novel catalytic activation of the leaving group in the S(N)2 reaction is achieved as an extension of our mercuric triflate-catalyzed reactions. Derivatives of anilinoethyl 4-pentynoate reacted smoothly with catalytic amounts of Hg(OTf)(2) to give indoline derivatives in excellent yield with efficient catalytic turnovers under very mild conditions. The reaction of optically pure secondary alcohol derivatives resulted in inversion of stereochemistry, which is a definitive feature of the S(N)2 reaction. The procedure is applicable for benzoazepine synthesis.
authors.affiliation: Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan.
authors.forename: Hirofumi
authors.initials: H
authors.lastname: Yamamoto
authors.forename: Ghanshyam
authors.initials: G
authors.lastname: Pandey
authors.forename: Yumiko
authors.initials: Y
authors.lastname: Asai
authors.forename: Mayo
authors.initials: M
authors.lastname: Nakano
authors.forename: Atsushi
authors.initials: A
authors.lastname: Kinoshita
authors.forename: Kosuke
authors.initials: K
authors.lastname: Namba
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Imagawa
authors.forename: Mugio
authors.initials: M
authors.lastname: Nishizawa
mesh_terms: D002384:Catalysis; D017669:Mercury Compounds / Q000737:chemistry; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*
chemical_list: D017669:Mercury Compounds; D009584:Nitrogen