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Amides as precursors of imidoyl radicals in cyclisation reactions
journal contribution
posted on 2007-11-15, 16:01 authored by W Bowman, Anthony J. Fletcher, Jan M. Pedersen, P.J. Lovell, Mark ElsegoodMark Elsegood, E.H. Lopez, Vickie McKee, G.B.S. PottsAmides 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. 191-203Publisher
© ElsevierPublication date
2007Notes
This article was published in the journal, Tetrahedron [© Elsevier] and is also available at: http://www.sciencedirect.com/science/journal/00404020ISSN
0040-4020Language
- en