A fluorobenzene adduct of Ti(IV), and catalytic carboamination to prepare alpha,beta-unsaturated imines and triaryl-substituted quinolines

Falguni Basuli; Halikhedkar Aneetha; John C Huffman; Daniel J Mindiola

doi:10.1021/ja0566026

A fluorobenzene adduct of Ti(IV), and catalytic carboamination to prepare alpha,beta-unsaturated imines and triaryl-substituted quinolines

J Am Chem Soc. 2005 Dec 28;127(51):17992-3. doi: 10.1021/ja0566026.

Authors

Falguni Basuli¹, Halikhedkar Aneetha, John C Huffman, Daniel J Mindiola

Affiliation

¹ Department of Chemistry and Molecular Structure Center, Indiana University, Bloomington, Indiana 47405, USA.

PMID: 16366536
DOI: 10.1021/ja0566026

Abstract

A rare fluorobenzene adduct of group 4, [(nacnac)Ti=NAr(FC6H5)][B(C6F5)4] (nacnac- = [ArNC(tBu)]2CH, Ar = 2,6-iPr2C6H3), 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 alpha,beta-unsaturated imines as well as triaryl-substituted quinolines. The latter product results from cyclization of the corresponding electron-rich alpha,beta-unsaturated imine.