Synthesis of phenanthridines by radical C(aryl)-C(aryl) coupling

Ana M. Rosa, Ana M. Lobo, Paula S. Branco, Sundaresan Prabhakar, António M. D. L. Pereira

Research output: Contribution to journalArticle

Abstract

Treatment of N-(o-bromobenzyl)anilines with 1-3 equivalent amounts of n-tributylinhydride, in the presence of 0.5 to 0.6 mol equiv. of AIBN, results in the formation of phenanthridines in good yields. The mechanism of the oxidation step is probed with a deuterated aniline derivative and azobiscyclohexylcarbanonitrile (ABCN) as the initiator. It is shown that the carbon centred radical derived from the latter does not act as the hydrogen abstracting species.

Original languageEnglish
Pages (from-to)269-284
Number of pages16
JournalTetrahedron
Volume53
Issue number1
DOIs
Publication statusPublished - 6 Jan 1997

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