Efficient synthesis of fluorinated benzimidazolines, benzothiazolines, benzoxazolines and dihydrobenzoxazinones using gallium (III) triflate as a catalyst

FLUO 2

G. K. Surya Prakash, gprakash@usc.edu, Thomas Mathew, Chiradeep Panja, Habiba Vaghoo, and George A. Olah, olah@usc.edu. Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, Los Angeles, CA 90089-1661
During our studies on the application of environmentally more benign, stable and reusable Lewis acid catalysts for various organic synthetic transformations we found that gallium(III) triflate is an effective water tolerant Lewis acid catalyst. Now we have extended our studies with this catalyst towards the synthesis of biologically active fluorinated heteroaromatics. We found that fluorinated benzimidazolines, benzothiazolines, benzoxazolines and dihydrobenzoxazinones can be synthesized very efficiently in high yields using gallium (III) triflate as a catalyst. The reactions can be tuned to form the corresponding heteroaromatics by proper selection of ortho-substituted anilines. The reactions are found to be very clean and the product work-up simple, requiring no further purification in most cases.
 

General Papers
1:30 PM-4:45 PM, Sunday, 10 September 2006 San Francisco Marriott -- Salon 5, Oral

Division of Fluorine Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006