Nonconventional carbon additions to azomethines. aryl amination/indoline synthesis by direct aryl radical addition to azomethine nitrogen.
[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.
Department of Chemistry, Indiana University, Bloomington, Indiana 47405-7102, USA. jnjohnst@indiana.edu
J N
JN
Johnston
M A
MA
Plotkin
R
R
Viswanathan
E N
EN
Prabhakaran