Journal
ORGANIC LETTERS
Volume 23, Issue 5, Pages 1572-1576Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c04281
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Funding
- MEXT [20H04818]
- Iketani Science and Technology Foundation
- JSPS
- Grants-in-Aid for Scientific Research [20H04818] Funding Source: KAKEN
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This study reports on the N-heterocyclic carbene (NHC)-catalyzed Truce-Smiles rearrangement of aniline derivatives, where an unactivated C(aryl)-N bond is cleaved to form a new C(aryl)-C bond. The key to the success of this reaction lies in the utilization of highly nucleophilic NFIC, which enables the formation of a highly nucleophilic ylide intermediate generated from an alpha,beta-unsaturated amide.
We report on the N-heterocyclic carbene (NHC)-catalyzed Truce-Smiles rearrangement of aniline derivatives, in which an unactivated C(aryl)-N bond is cleaved, leading to the formation of a new C(aryl)-C bond. The key to the success of this reaction is the utilization of a highly nucleophilic NFIC, which enables the formation of a highly nucleophilic ylide intermediate that is generated from an alpha,beta-unsaturated amide.
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