Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

OMS-2-Supported Cu Hydroxide-Catalyzed Benzoxazoles Synthesis from Catechols and Amines via Domino Oxidation Process at Room Temperature

OMS-2-Supported Cu Hydroxide-Catalyzed Benzoxazoles Synthesis from Catechols and Amines via Domino Oxidation Process at Room Temperature
Peiqing Zhao, Xu Meng, Yuanguang Wang, Zhenqiang Jing, Yanmin Wang, Baohua Chen, Gexin Chen
In the presence of manganese oxide octahedral molecular sieve (OMS-2) supported copper hydroxide Cu(OH)x/OMS-2, aerobic synthesis of benzoxazoles from catechols and amines via domino oxidation/cyclization at room temperature is achieved. This heterogeneous benzoxazoles synthesis initiated by the efficient oxidation of catechols over Cu(OH)x/OMS-2 tolerates a variety of substrates, especially amines containing sensitive groups (hydroxyl, cyano, amino, vinyl, ethynyl, ester, and even acetyl groups) and heterocycles, which affords functionalized benzoxazoles in good to excellent yields by employing low catalyst loading (2 mol % Cu). The characterization and plausible catalytic mechanism of Cu(OH)x/OMS-2 are described. The notable features of our catalytic protocol such as the use of air as the benign oxidant and EtOH as the solvent, mild conditions, ease of product separation, being scalable up to the gram level, and superior reusability of catalyst (up to 10 cycles) make it more practical and environmentally friendly for organic synthesis.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01119

DOI: 10.1021/acs.joc.7b01119

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