{Reference Type}: Journal Article
{Title}: NHC Catalysis for Umpolung Pyridinium Alkylation via Deoxy-Breslow Intermediates.
{Author}: Wu T;Tatton MR;Greaney MF;
{Journal}: Angew Chem Int Ed Engl
{Volume}: 61
{Issue}: 15
{Year}: 04 2022 4
{Factor}: 16.823
{DOI}: 10.1002/anie.202117524
{Abstract}: Umpolung N-heterocyclic carbene (NHC) catalysis of non-aldehyde substrates offers new pathways for C-C bond formation, but has proven challenging to develop in terms of viable substrate classes. Here, we demonstrate that pyridinium ions can undergo NHC addition and subsequent intramolecular C-C bond formation through a deoxy-Breslow intermediate. The alkylation demonstrates, for the first time, that deoxy-Breslow intermediates are viable for catalytic umpolung of areniums.