OMS-2-Supported Cu Hydroxide-Catalyzed Benzoxazoles Synthesis from Catechols and Amines via Domino Oxidation Process at Room Temperature
DepartmentERC国家工程研究中心
Meng X(孟旭)1; Wang YG(王圆广)1; Wang YM(王艳敏)1; Chen BH(陈保华)2; Jing ZQ(景震强)3; Chen GX(陈革新)1; Zhao PQ(赵培庆)1; Zhao PQ(赵培庆)
The second department苏州研究院;osso国家重点实验室
2017
Source PublicationThe Journal of Organic Chemistry
ISSN0022-3263
Volume82Issue:13Pages:6922-6931
Abstract

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.

Subject Area物理化学与绿色催化
DOI10.1021/acs.joc.7b01119
Funding Organizationthe National Natural Science Foundation of China (Grants 21403256 ; 21573261 ; 21372102) ; the Suzhou Industrial Technology and Innovation Project (Grant SYG201531)
Indexed BySCI
If4.805
Language英语
Funding Project催化新工艺研究组
compositor第一作者单位
Citation statistics
Cited Times:48[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.licp.cn/handle/362003/21920
Collection精细石油化工中间体国家工程研究中心(ERC)
羰基合成与选择氧化国家重点实验室(OSSO)
苏州研究院
Corresponding AuthorZhao PQ(赵培庆)
Affiliation1.State Key Laboratory for Oxo Synthesis and Selective Oxidation, Suzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou 730000, P. R. China
2.State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. China
3.Suzhou Institute of Nano-Tech and Nano-Bionic (SINANO), Chinese Academy of Sciences, Suzhou 215123, P. R. China
Recommended Citation
GB/T 7714
Meng X,Wang YG,Wang YM,et al. OMS-2-Supported Cu Hydroxide-Catalyzed Benzoxazoles Synthesis from Catechols and Amines via Domino Oxidation Process at Room Temperature[J]. The Journal of Organic Chemistry,2017,82(13):6922-6931.
APA Meng X.,Wang YG.,Wang YM.,Chen BH.,Jing ZQ.,...&Zhao PQ.(2017).OMS-2-Supported Cu Hydroxide-Catalyzed Benzoxazoles Synthesis from Catechols and Amines via Domino Oxidation Process at Room Temperature.The Journal of Organic Chemistry,82(13),6922-6931.
MLA Meng X,et al."OMS-2-Supported Cu Hydroxide-Catalyzed Benzoxazoles Synthesis from Catechols and Amines via Domino Oxidation Process at Room Temperature".The Journal of Organic Chemistry 82.13(2017):6922-6931.
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