N- versus O-Arylation of Aminoalcohols: Orthogonal Selectivity in Copper-Based Catalysts

Link: http://pubs.acs.org/cgi-bin/abstract.cgi/jacsat/asap/abs/ja068926f.html

From Prof. Stephen L. Buchwald's group at MIT

Orthogonal Copper-based catalyst systems which complement each other in the selective arylation of aminoalcohols was recently reported in JACS ASAP. The selectivity can be altered by switching the type of ligand used in the reaction. One major limitation is that if the O-arylated product is desired, the N and O in the chain of the aminoalcohol have to be at least four carbons apart to obtain good to excellent selectivity and yields. If the N-arylated product is desired, then the N and O have to be at least three carbons apart.