A Simple One-pot Organometallic Formylation/Trapping Sequence Using N-Formylcarbazole
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.
carbinols - enynes - formylation - heterocycles - N-formylcarbazole