Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 1, Pages 42-52Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b01503
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Funding
- CSIR [02(0250)/15/EMR-II]
- UGC-JRF [CH/16-17/0018]
- SERB-NPDF [PDF/2015/000144]
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The N-heterocycle carbene (NHC)-catalyzed dual Stetter cascade reaction is discovered through coupling of beta-nitrostyrene with phthalaldehyde under mild conditions to furnish valuable arylnaphthoquinones. The generality of the new reaction is validated through the development of a C-C and O-C bond forming Stetter cascade reaction using salicylaldehydes to obtain functionalized dihydroisoflavanones. The mild NHC organocatalysis is successfully employed for the construction of optically pure sugar-based naphthoquinones and dihydroisoflavanones. Herein, NHC is found as a unique and powerful organocatalyst to construct homoatomic C-C cross-coupling, heteroatomic O-C bond formation, and cascade cyclization utilizing NO2 as a leaving group at ambient temperature. A mechanistic pathway of the new metal-free catalysis is predicted on the basis of our ESI-MS study of the ongoing reaction and literature.
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