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Amides as precursors of imidoyl radicals in cyclisation reactions

journal contribution
posted on 15.11.2007 by W Bowman, Anthony J. Fletcher, Jan M. Pedersen, P.J. Lovell, Mark Elsegood, E.H. Lopez, Vickie McKee, G.B.S. Potts
Amides have been successfully used as precursors of imidoyl radicals for radical cyclisation. The amides have been converted to imidoyl selanides via reaction with phosgene to yield imidoyl chlorides followed by reaction with potassium phenylselanide. Imidoyl selanides were reacted with tributyltin hydride (Bu3SnH) as the radical mediator with triethylborane or AIBN as initiators to yield imidoyl radicals for cyclisation reactions. Imidoyl radicals have been cyclised onto alkenes to yield 2,3-substituted-indoles and -quinolines and also onto pyrroles and indoles to give bi- and tricyclic heteroarenes.

History

School

  • Science

Department

  • Chemistry

Citation

BOWMAN et al, 2007. Amides as precursors of imidoyl radicals in cyclisation reactions. Tetrahedron, 63(1), pp. 191-203

Publisher

© Elsevier

Publication date

2007

Notes

This article was published in the journal, Tetrahedron [© Elsevier] and is also available at: http://www.sciencedirect.com/science/journal/00404020

ISSN

0040-4020

Language

en

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