Facile N-arylation of amines and sulfonamides and O-arylation of phenols and carboxylic acids

ORGN 304

Zhijian Liu and Richard C. Larock. Department of Chemistry, Iowa State University, 1605 Gilman Hall, Ames, IA 50011
A facile transition-metal free N-arylation of amines, amides and sulfonamides and O-arylation of phenols and acids has been developed using ó-trimethylsilylaryl triflates and CsF. This affords good to excellent yields of arylated products under very mild reaction conditions. A methoxy-substituted silylaryl triflate reacts with various nucleophiles to afford O-and N-arylated products with high yield and excellent regioselectivity. This chemistry tolerates a variety of functional groups and can be extended to the synthesis of a variety of potentially biologically active products.

 

New Reactions and Methodology
8:00 AM-12:00 PM, Tuesday, September 9, 2003 Sheraton New York -- Royal Ballroom B, Oral

Division of Organic Chemistry
The 226th ACS National Meeting, New York, NY, September 7-11, 2003