Synlett 2004(6): 1092-1094  
DOI: 10.1055/s-2004-822896
© Georg Thieme Verlag Stuttgart · New York

A Simple One-pot Organometallic Formylation/Trapping Sequence Using N-Formylcarbazole

Darren J. Dixon*, Amanda C. Lucas
University Chemical Laboratory, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, UK
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Further Information

Publication History

Received 30 January 2004
Publication Date:
25 March 2004 (eFirst)


Treatment of a range of sp3-, sp2- and sp-nucleophiles with N-formyl carbazole leads to the formation of the metastable anionic carbazole carbinols. In the presence of a second nucleophilic reagent such as phosphonoacetate or an organolithium, these collapse on warming to the aldehyde which is trapped in situ to afford the α,β-unsaturated esters or secondary carbinols respectively.