Nonconventional carbon additions to azomethines. Aryl amination/indoline synthesis by direct aryl radical addition to azomethine nitrogen

…, MA Plotkin, R Viswanathan, EN Prabhakaran

Index: Johnston, Jeffrey N.; Plotkin, Michael A.; Viswanathan, Rajesh; Prabhakaran, Erode N. Organic Letters, 2001 , vol. 3, # 7 p. 1009 - 1011

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Citation Number: 51

Abstract

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 n Bu3SnH 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 π-bonds.