An NHC-Catalyzed Desulfonylative Smiles Rearrangement of Pyrrole and Indole Carboxaldehydes

The use of catalysismethods to enable Smiles rearrangementopensup new substrate classes for arylation under mild conditions. Here,we describe an N-heterocyclic carbene (NHC) catalysis system thataccesses indole and pyrrole aldehyde substrates in a desulfonylativeSmiles process. The reaction proceeds under mild, transition-metal-freeconditions and captures acyl anion reactivity for the synthesis ofa diverse array of 2-aroyl indoles and pyrroles from readily availablesulfonamide starting materials.

Automated summary

The use of catalysis methods enables the Smiles rearrangement and opens up new substrate classes under mild conditions. In this study, a N-heterocyclic carbene (NHC) catalysis system is described, which allows for the access of indole and pyrrole aldehyde substrates in a desulfonylative Smiles process. The reaction proceeds under mild, transition-metal-free conditions and synthesizes a diverse array of 2-aroyl indoles and pyrroles from readily available sulfonamide starting materials.