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Synfacts 2013; 9(1): 0085
DOI: 10.1055/s-0032-1317737
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Phenanthridine Derivatives via Oxidative Cyclization

Contributor(s):
Paul Knochel
,
Christoph Sämann
Tobisu M, * Koh K, Furukawa T, Chatani N. * Osaka University, Japan
Modular Synthesis of Phenanthridine Derivatives by Oxidative Cyclization of 2-Isocyanobiphenyls with Organoboron Reagents.

Angew. Chem. Int. Ed. 2012;
51: 11363-11366
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Further Information

Publication History

Publication Date:
17 December 2012 (online)

 
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Key words

phenanthridine derivatives - organoboron reagents - oxidative cyclization - manganese

Significance

A straight-forward synthesis of a broad range of phenanthridine derivatives via a manganese-mediated annulation of 2-isocyano­biaryls with organoboronic acids has been disclosed. This rapid and divergent reaction furnishes the corresponding phenanthridine derivatives in good yield.


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Comment

The reported reaction shows a simple pathway for the synthesis of phenanthridine frameworks out of readily accessible starting materials. Furthermore, mechanistic studies indicate that the reaction proceeds by the intramolecular homolytic aromatic substitution of an imidoyl radical intermediate.


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