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

Abstract

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.

Key words

carbinols - enynes - formylation - heterocycles - N-formylcarbazole

References

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