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