Understanding the behavior of N-tosyl and N-2-pyridylsulfonyl imines in CuII-catalyzed aza-Friedel-Crafts reactions

J Org Chem. 2008 Aug 15;73(16):6401-4. doi: 10.1021/jo800986g. Epub 2008 Jul 9.

Abstract

The different behavior of N-tosyl imines and N-(2-pyridyl)sulfonyl imines in Cu (II)-catalyzed AFCR is described. DFT theoretical calculations on the mode of coordination of the copper atom to both types of substrates allow understanding this different reactivity.