4.7 Article

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

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JOURNAL OF ORGANIC CHEMISTRY
卷 88, 期 17, 页码 12821-12825

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AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.3c01089

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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.
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.

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