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

ABSTRACT: The use of catalysis methods to enable Smiles rearrangement opens up new substrate classes for arylation under mild conditions. Here, we describe an N-heterocyclic carbene (NHC) catalysis system that accesses indole and pyrrole aldehyde substrates in a desulfonylative Smiles process. The reaction proceeds under mild, transition-metal-free conditions and captures acyl anion reactivity for the synthesis of a diverse array of 2-aroyl indoles and pyrroles from readily available sulfonamide starting materials.

SUBMITTER: Swaby C

PROVIDER: S-EPMC10476196 | biostudies-literature | 2023 Sep

REPOSITORIES: biostudies-literature

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

Swaby Caitlin C Taylor Alfie A Greaney Michael F MF

The Journal of organic chemistry 20230817 17

The use of catalysis methods to enable Smiles rearrangement opens up new substrate classes for arylation under mild conditions. Here, we describe an N-heterocyclic carbene (NHC) catalysis system that accesses indole and pyrrole aldehyde substrates in a desulfonylative Smiles process. The reaction proceeds under mild, transition-metal-free conditions and captures acyl anion reactivity for the synthesis of a diverse array of 2-aroyl indoles and pyrroles from readily available sulfonamide starting ...[more]

PMID: 37589318

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