Ipso-Nitration of arylboronic acids: Chlorotrimethylsilane-nitrate salt as an efficient reagent system

ORGN 50

G. K. Surya Prakash, Chiradeep Panja, Vijayalakshmi Surampudi, Nicos A. Petasis, Thomas Mathew, and George A. Olah. Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, Los Angeles, CA 90089-1661
A mixture of nitrate salt and chlorotrimethylsilane is found to be an efficient regioselctive nitrating agent for the ipso-nitration of arylboronic acids to produce the nitroarenes in good to excellent yields often with 95-98% purity in the crude product itself. High selectivity, simplicity and cleanness of the reaction are the key features. The reactions are easy to perform and work up, avoiding further purification in most cases. Formation of dinitro products is absent.

 

New Reactions and Methodology, Metal-Mediated Reactions, Heterocycles and Aromatics
8:00 PM-10:00 PM, Sunday, March 28, 2004 Anaheim Convention Center -- Hall A, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, March 29, 2004 Anaheim Convention Center -- Hall A, Sci-Mix

Division of Organic Chemistry

The 227th ACS National Meeting, Anaheim, CA, March 28-April 1, 2004