We report the Lewis acid catalysis of aryldiazonium salts,and their Lewis acidity applications in photogeneration of aryl radicals under additive-,photocatalyst-and transition metal-free conditions.In this visible lig...We report the Lewis acid catalysis of aryldiazonium salts,and their Lewis acidity applications in photogeneration of aryl radicals under additive-,photocatalyst-and transition metal-free conditions.In this visible light-mediated transformation,the Lewis acidic character of aryldiazonium salts enables access to the photoactive charge transfer complex with dichalcogenides.The usefulness and versatility of this new protocol are demonstrated through the chalcogenation of a variety of aryldiazonium salts.展开更多
Asymmetric synthesis of enantioenriched azo compounds bearing tetrasubstituted stereocenter was achieved through chiral N,N′-dioxide/metal Lewis acid promoted interrupted Japp-Klingemann reaction of aryldiazonium tet...Asymmetric synthesis of enantioenriched azo compounds bearing tetrasubstituted stereocenter was achieved through chiral N,N′-dioxide/metal Lewis acid promoted interrupted Japp-Klingemann reaction of aryldiazonium tetrafluoroborate salts with nucleophiles under mild conditions. This protocol features wide substrate scope and good functional group compatibility.Azaarene-containing chiral azo compounds were stable enough in Japp-Klingemann reaction condition. The key to success of the reaction was the employment of metal salt/N,N′-dioxide ligand and the dual-task roles of the base. Moreover, the X-ray crystal structure of Ni(II)/N,N′-dioxide/substrate complex confirmed that the substrate was activated by bidentate coordination, which shed light on the origin of chiral control of the reaction.展开更多
A visible-light-catalyzed synthesis of indol-3-yl aryl ketones from aryldiazonium salts, CO and indoles at room temperature was developed. This process provides a useful method for the preparation of diverse indol-3-y...A visible-light-catalyzed synthesis of indol-3-yl aryl ketones from aryldiazonium salts, CO and indoles at room temperature was developed. This process provides a useful method for the preparation of diverse indol-3-yl aryl ketones from readily accessible reactants under base-free, acid-free and transition-metalfree conditions.展开更多
Generation of 3-sulfonated 2 H-pyrrol-2-ones through a three-component reaction of allenoic amides,sulfur dioxide,and aryldiazonium tetrafluoroborates under metal-free conditions is achieved.This transformation procee...Generation of 3-sulfonated 2 H-pyrrol-2-ones through a three-component reaction of allenoic amides,sulfur dioxide,and aryldiazonium tetrafluoroborates under metal-free conditions is achieved.This transformation proceeds under mild conditions without the addition of catalysts or additives,giving rise to 3-sulfonated 2 H-pyrrol-2-ones in moderate to good yields.Good functional group compatibility is observed.A plausible mechanism is proposed,which is initiated by aryl radicals formed in situ from aryldiazonium tetrafluoroborates and DABCO·(SO2)2.Additionally,excellent chemoselectivity and regioselectivity are presented in this transformation.展开更多
基金financial support from the National Natural Science Foundation of China(Nos.22001248 and 22173103)the Fundamental Research Funds for the Central Universities and the University of the Chinese Academy of Sciences。
文摘We report the Lewis acid catalysis of aryldiazonium salts,and their Lewis acidity applications in photogeneration of aryl radicals under additive-,photocatalyst-and transition metal-free conditions.In this visible light-mediated transformation,the Lewis acidic character of aryldiazonium salts enables access to the photoactive charge transfer complex with dichalcogenides.The usefulness and versatility of this new protocol are demonstrated through the chalcogenation of a variety of aryldiazonium salts.
基金supported by the National Natural Science Foundation of China(21890723,21921002)。
文摘Asymmetric synthesis of enantioenriched azo compounds bearing tetrasubstituted stereocenter was achieved through chiral N,N′-dioxide/metal Lewis acid promoted interrupted Japp-Klingemann reaction of aryldiazonium tetrafluoroborate salts with nucleophiles under mild conditions. This protocol features wide substrate scope and good functional group compatibility.Azaarene-containing chiral azo compounds were stable enough in Japp-Klingemann reaction condition. The key to success of the reaction was the employment of metal salt/N,N′-dioxide ligand and the dual-task roles of the base. Moreover, the X-ray crystal structure of Ni(II)/N,N′-dioxide/substrate complex confirmed that the substrate was activated by bidentate coordination, which shed light on the origin of chiral control of the reaction.
基金supported by the National Key Research and Development Program of China(No.2021YFA1500703 to Ganglong Cui)Distinguished Professorship of Chang Jiang Scholars of Ministry of Education of China(Ganglong Cui)+1 种基金the Fundamental Research Funds for the Central Universitiesthe National Natural Science Foundation of China(No.22233001 to Ganglong Cui,No.22003043 to Xiang-Yang Liu)。
基金We thank Prof. Yang Gan of Harbin Institute of Technology, and Prof. Fu-long Yuan of Heilongjiang University for the help in the experiments. This work was supported by the Center for Precision Engineering of Harbin Institute of Technology, the Youth the Colleges and Universities in Heilongjiang Province in 2010 （No.1155G54）, the Training Fund Project of Jiamusi University （No.RC2009-037）, and the National Natural Science Foundation of China （No.51105174）.
基金the financial support from the Educational Bureau of Yunnan Province (No. 2010Y431)the State Ethnic Affairs Commission (No. 12YNZ05)
文摘A visible-light-catalyzed synthesis of indol-3-yl aryl ketones from aryldiazonium salts, CO and indoles at room temperature was developed. This process provides a useful method for the preparation of diverse indol-3-yl aryl ketones from readily accessible reactants under base-free, acid-free and transition-metalfree conditions.
基金the National Natural Science Foundation of China(Nos.21871053 and 21532001)the Leading Innovative and Entrepreneur Team Introduction Program of Zhejiang(No.2019R01005)。
文摘Generation of 3-sulfonated 2 H-pyrrol-2-ones through a three-component reaction of allenoic amides,sulfur dioxide,and aryldiazonium tetrafluoroborates under metal-free conditions is achieved.This transformation proceeds under mild conditions without the addition of catalysts or additives,giving rise to 3-sulfonated 2 H-pyrrol-2-ones in moderate to good yields.Good functional group compatibility is observed.A plausible mechanism is proposed,which is initiated by aryl radicals formed in situ from aryldiazonium tetrafluoroborates and DABCO·(SO2)2.Additionally,excellent chemoselectivity and regioselectivity are presented in this transformation.
