Tetrahedron

Bu 3 SnH-mediated radical cyclisation onto azoles

…, WR Bowman, E Bridge, MRJ Elsegood, T McInally…

Index: Allin, Steven M.; Barton, William R.S.; Russell Bowman; Bridge (nee Mann), Emma; Elsegood, Mark R.J.; McInally, Tom; McKee, Vickie Tetrahedron, 2008 , vol. 64, # 33 p. 7745 - 7758

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Citation Number: 40

Abstract

Alkyl radicals have been cyclised onto pyrroles, imidazoles and pyrazoles, and acyl radicals cyclised onto pyrroles, using Bu3SnH-,(TMS) 3SiH-and Bu3GeH-mediated aromatic homolytic substitution for the synthesis of bicyclic N-heterocycles. The reactions yield intermediate π-radicals that lose hydrogen in the rearomatisation step of the aromatic homolytic substitution. Mechanistic studies of these rearomatisation steps indicate ...