Triphenylphosphine-mediated reductive cyclization of 2-nitrobiphenyls: a practical and convenient synthesis of carbazoles

AW Freeman, M Urvoy, ME Criswell

Index: Freeman, Adam W.; Urvoy, Marie; Criswell, Megan E. Journal of Organic Chemistry, 2005 , vol. 70, # 13 p. 5014 - 5019

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Citation Number: 162

Abstract

The synthesis of a series of substituted carbazoles from the corresponding 2-nitrobiphenyl derivatives using a novel modification of the Cadogan reaction is described. Cyclization of the 2-nitrobiphenyls was achieved via reductive deoxygenation of the nitro groups using a slight excess of triphenylphosphine in a suitable solvent. We have observed a temperature dependence on the extent of conversion under these conditions, with higher boiling ...

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