A Fluorobenzene Adduct of Ti(IV), and Catalytic Carboamination to Prepare α,β-Unsaturated Imines and Triaryl-Substituted Quinolines

• Published in: Journal of the American Chemical Society Vol. 127; no. 51; pp. 17992 - 17993
• Main Authors: Basuli, Falguni, Aneetha, Halikhedkar, Huffman, John C, Mindiola, Daniel J
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 28.12.2005; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Multidisciplinary; Exact sciences and technology; Kinetics and mechanisms; Organic chemistry; Physical Sciences; Reactivity and mechanisms; Science & Technology; IMIDO COMPLEXES; ALKENES; MECHANISM; INTERMOLECULAR HYDROAMINATION; REGIOCHEMISTRY; REACTIVITY; ALKYNES; TITANIUM; MARKOVNIKOV; CATIONS; Catalytic reaction; Nitrogen heterocycle; Catalyst selectivity; Quinoline derivatives; Transition metal Complexes; Complex catalyst; Experimental study; Tolan; Aldimine; Titanium Complexes; Imido complex; Bicyclic compound; Reaction mechanism; Aromatic compound; Catalyst activity
• ISSN: 0002-7863; 1520-5126
• DOI: 10.1021/ja0566026

A rare fluorobenzene adduct of group 4, [(nacnac)TiNAr(FC6H5)][B(C6F5)4] (nacnac- = [ArNC( t Bu)]2CH, Ar = 2,6- i Pr2C6H3), has been isolated and structurally characterized. This highly electron-deficient system engages readily in imine metathesis and catalyzes carboamination reactions involving diphenylacetylene and aldimines to afford α,β-unsaturated imines as well as triaryl-substituted quinolines. The latter product results from cyclization of the corresponding electron-rich α,β-unsaturated imine.