Nonconventional Carbon Additions to Azomethines. Aryl Amination/Indoline Synthesis by Direct Aryl Radical Addition to Azomethine Nitrogen

Abstract

[reaction: see text]. The generality of a new method for aryl amination has been defined. Ketimines derived from o-bromophenethylamine cyclize to the N-substituted indoline when treated with nBu3SnH and a radical initiator. The pH-neutral conditions tolerate base- and acid-sensitive functionality. The observed regioselectivity is nonconventional for addition reactions involving carbon radicals and carbon-heteroatom pi-bonds.