7664-86-0Relevant articles and documents
Stable Boron Peroxides with a Subporphyrinato Ligand
Tsurumaki, Eiji,Sung, Jooyoung,Kim, Dongho,Osuka, Atsuhiro
, p. 2596 - 2599 (2016)
Subporphyrin B-peroxides have been synthesized in good yields by acid-catalyzed exchange reactions of subporphyrin B-methoxide with the corresponding hydroperoxides. Thermal dimerization of the subporphyrin B-hydroperoxide provided the peroxo-bridged bis(subporphyrin) quantitatively. These subporphyrin B-peroxides are fairly stable under ambient conditions, which allowed their isolation and full characterization as the first examples of structurally authenticated boron hydroperoxides, acyclic boron organylperoxides, and neutral peroxo-bridged diboron species. The subporphyrin B-peroxides thus prepared were investigated through their crystal structures, IR spectra, and cyclic voltammograms as well as by DFT calculations. The subporphyrin B-hydroperoxide oxidizes triphenylphosphine quantitatively to triphenylphosphine oxide. Acid-catalyzed exchange reactions of a subporphyrinatoboron methoxide with a range of hydroperoxides have resulted in the synthesis of a series of boron peroxides with a subporphyrinato ligand. The boron peroxides are prepared in good yields and are fairly stable under ambient conditions, thus allowing their isolation and full characterization as the first examples of structurally authenticated neutral and acyclic boron peroxides.
Merging Photoredox with Br?nsted Acid Catalysis: The Cross-Dehydrogenative C?O Coupling for sp3 C?H Bond Peroxidation
Xia, Qing,Wang, Qiang,Yan, Changcun,Dong, Jianyang,Song, Hongjian,Li, Ling,Liu, Yuxiu,Wang, Qingmin,Liu, Xiangming,Song, Haibin
supporting information, p. 10871 - 10877 (2017/08/18)
A photoredox and Br?nsted acid synergistically catalyzed cross-dehydrogenative C?O coupling reaction is developed in which isochroman peroxyacetals are formed through sp3 C?H bond peroxidation. The reported method is characterized by its extremely mild reaction conditions, excellent yields, and broad substrate scope. An oxocarbenium ion p-chlorobenzenesulfonate was speculated to be the reactive intermediate. The role of hemiacetals and oxygenated dimers on the effective stabilization of the oxocarbenium ion was investigated; the presence of acid appeared to establish equilibrium between hemiacetals and oxygenated dimers with the oxocarbenium ion pairs. The broad applicability of the method highlights the potential of the protocol for molecule synthesis.
A metal-free catalytic system for the oxidation of benzylic methylenes and primary amines under solvent-free conditions
Zhang, Jintang,Wang, Zhentao,Wang, Ye,Wan, Changfeng,Zheng, Xiaoqi,Wang, Zhiyong
scheme or table, p. 1973 - 1978 (2010/06/15)
Iodine-pyridine-tert-butylhydroperoxide is developed as a green and efficient catalytic system for the oxidation of benzylic methylenes to ketones and primary amines to nitriles. The reaction conditions are quite mild and environmentally benign, no transition metals, organic solvents or hazard reagents being needed. The oxidation of benzylic methylenes gave the corresponding ketones in excellent yields with complete chemoselectivity, while the oxidation of primary amines was complete in several minutes, affording various nitriles in moderate to good yields.
