18690-79-4Relevant articles and documents
An Organotransition-Metal Synthesis of Naphthoquinones
Liebeskind, Lanny S.,Baysdom, Sherrol L.,South, Mivhael S.
, p. 7397 - 7398 (1980)
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New, simple and selective synthesis of perfluoroalkylquinones by perfluoroalkyl radicals - Enthalpic and polar effects
Antonietti, Fabrizio,Gambarotti, Cristian,Mele, Andrea,Minisci, Francesco,Paganelli, Roberto,Punta, Carlo,Recupero, Francesco
, p. 4434 - 4440 (2005)
Perfluoroalkyl radicals (Rf), generated by iodine abstraction from perfluoroalkyl iodides by phenyl radicals, react selectively with quinone rings in spite of their electrophilic character. In the presence of electron-rich alkenes, Rf/sub
NHC-Catalyzed Dual Stetter Reaction: A Mild Cascade Annulation for the Syntheses of Naphthoquinones, Isoflavanones, and Sugar-Based Chiral Analogues
Mitra, Rajendra N.,Show, Krishanu,Barman, Debabrata,Sarkar, Satinath,Maiti, Dilip K.
, p. 42 - 52 (2019/01/10)
The N-heterocycle carbene (NHC)-catalyzed dual Stetter cascade reaction is discovered through coupling of β-nitrostyrene with phthalaldehyde under mild conditions to furnish valuable aryl-naphthoquinones. 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.
CuI/Cu(OTf)2/DMSO system-catalyzed intramolecular oxidative cyclization of (o-alkynyl)arylketones: Efficient synthesis of 1,4-naphthoquinones
Zhou, Bingwei,Liu, Qian,Wang, Heng,Jin, Hongwei,Liu, Yunkui
, p. 3815 - 3821 (2019/06/14)
A concise and efficient method for the synthesis of 1,4-naphthoquinones has been successfully developed involving a CuI/Cu(OTf)2/DMSO system-catalyzed intramolecular oxidative cyclization of (o-alkynyl)arylketones. The present protocol provided a novel approach to access functionalized 1,4-naphthoquinones from non-naphthoquinone precursors with good selectivity and functional group tolerance.