Rhenium-Catalyzed Formation of Indene Frameworks via C−H Bond Activation:  [3+2] Annulation of Aromatic Aldimines and Acetylenes

• Published in: Journal of the American Chemical Society Vol. 127; no. 39; pp. 13498 - 13499
• Main Authors: Kuninobu, Yoichiro, Kawata, Atsushi, Takai, Kazuhiko
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 05.10.2005; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Multidisciplinary; Exact sciences and technology; Kinetics and mechanisms; Organic chemistry; Physical Sciences; Reactivity and mechanisms; Science & Technology; FUNCTIONALIZATION; KETONES; COMPLEXES; ESTERS; ALDEHYDES; ALKYNES; DERIVATIVES; Catalytic reaction; Aliphatic compound; Catalyst selectivity; Transition metal Carbonyl Complexes; Complex catalyst; Experimental study; Aldimine; Acetylene derivatives; Annelation; Rhenium Carbonyl Complexes; Bicyclic compound; Reaction mechanism; Benzenic compound; Chloro complex; Aromatic compound; Indene derivatives; Catalyst activity; Benzaldehyde derivatives
• ISSN: 0002-7863; 1520-5126
• DOI: 10.1021/ja0528174

A rhenium complex, [ReBr(CO)3(thf)]2, catalyzes the reaction of an aromatic aldimine with an acetylene to give an indene derivative in a quantitative yield. The reaction proceeds via C−H bond activation, insertion of the acetylene, intramolecular nucleophilic cyclization, and reductive elimination. In contrast to ruthenium and rhodium catalysts, which are usually employed in this type of reaction, the rhenium catalyst promotes the intramolecular nucleophilic cyclization of the alkenylmetal species generated by insertion of the acetylene.