Selectfluor promoted NHC–oxazoline gold(i) complex catalyzed cycloaddition/oxidation reaction of enynones with alkenes

文献情報

出版日 2015-09-02

DOI 10.1039/C5QO00155B

インパクトファクター 5.281

著者

Qin Xu, Peng Gu, Feijun Wang

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要旨

The ortho- and meta-substituted NHC–oxazoline ligands based on a phenyl scaffold have been synthesized in a six-step pathway, and their coordination with Au(Me2S)Cl gave the corresponding NHC–gold(I) complexes in good yields. Resulting from restricted rotation between the phenyl ring and the benzimidazole ring, the ortho-substituted NHC–oxazoline gold(I) complexes exhibited as a pair of diastereomers, and their structures have been further confirmed by X-ray diffraction analysis. Moreover, combination of these gold(I) complexes with Selectfluor in situ was used to catalyze the reaction of enynone with alkenes using air as an oxidant to give naphthalene derivatives in moderate to excellent yields. Some controlled experiments were carried out to reveal the active species as a chelated NHC–oxazoline gold(I) species and the role Selecfluor played in this reaction.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

Selectfluor promoted NHC–oxazoline gold(i) complex catalyzed cycloaddition/oxidation reaction of enynones with alkenes

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