Use of gallium(III) triflate as an efficient Lewis acid catalyst for multicomponent and cyclization reactions

ORGN 539

G. K. Surya Prakash, gprakash@usc.edu, Thomas Mathew, Habiba Vaghoo, Chiradeep Panja, and George A. Olah, olah@usc.edu. Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, Los Angeles, CA 90089-1661
Application of gallium(III) triflate as stable, environmentally benign, and reusable Lewis acid catalysts for various organic synthetic transformations has been recently explored in our laboratory. We found that gallium(III) triflate is an effective catalyst for multicomponent reactions such as Strecker reaction and Biginelli reaction. We have also achieved the convergent synthesis of fluorinated heteroaromatics such as fluorinated benzimidazolines, benzothiazolines, benzoxazolines and dihydrobenzoxazinones. 1,5-Benzodiazepine derivative was obtained when acetone was used instead of the fluorinated ketones. Simplicity, catalytic efficiency and the mechanistic aspects of both fluorinated and nonfluorinated version of these reactions will be depicted in detail.