Direct Synthesis of α-Alkoxy Ketones by Oxidative C-O Bond Formation

被引:15
作者
Yu, Hui [1 ]
Xu, Yilan [1 ]
Fang, Yan [1 ]
Dong, Rui [1 ]
机构
[1] Tongji Univ, Dept Chem, Siping Rd 1239, Shanghai 200092, Peoples R China
关键词
Synthetic methods; Ketones; C-O bond formation; Oxidation; Oxidative coupling; LEWIS-ACID CONDITIONS; N-TOSYLHYDRAZONES; METAL-FREE; TRANSFER HYDROGENATION; ASYMMETRIC-SYNTHESIS; INSERTION REACTIONS; CONSTRUCTION; TBAI/TBHP; CATALYST; ACCESS;
D O I
10.1002/ejoc.201600723
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A convenient method to prepare alpha-alkoxy ketones has been developed by oxidative coupling of aryl methyl ketones and alcohols. With aqueous tert-butyl hydroperoxide (6.0 equiv.) as the oxidant, tetrabutylammonium iodide (20 mol-%) as the catalyst, and TsNHNH2 (1.0 equiv.) as the additive, ketones underwent direct alkoxylation to give alpha-methoxy or alpha-ethoxy ketones in moderate to good yields.
引用
收藏
页码:5257 / 5262
页数:6
相关论文
共 55 条
[51]   Transition-metal-free decarboxylation of dimethyl malonate: an efficient construction of α-amino acid esters using TBAI/TBHP [J].
Zhang, Jie ;
Shao, Ying ;
Wang, Yaxiong ;
Li, Huihuang ;
Xu, Dongmei ;
Wan, Xiaobing .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (13) :3982-3987
[52]   Dual Roles of Sulfonyl Hydrazides: A Three-Component Reaction To Construct Fully Substituted Pyrazoles Using TBAI/TBHP [J].
Zhang, Jie ;
Shao, Ying ;
Wang, Hongxiang ;
Luo, Qiang ;
Chen, Jijun ;
Xu, Dongmei ;
Wan, Xiaobing .
ORGANIC LETTERS, 2014, 16 (12) :3312-3315
[53]   Ruthenium ONO-Type Pincer Complex: Synthesis, Structural Characterization, and Catalysis [J].
Zhang, Yao ;
Li, Xingwei ;
Hong, Soon Hyeok .
ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (10) :1779-1783
[54]   Electrochemical Synthesis of the Aryl α-Ketoesters from Acetophenones Mediated by KI [J].
Zhang, Zhenlei ;
Su, Jihu ;
Zha, Zhenggen ;
Wang, Zhiyong .
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (52) :17711-17714
[55]   Sodium Iodide-Catalyzed Direct α-Alkoxylation of Ketones with Alcohols via Oxidation of α-Iodo Ketone Intermediates [J].
Zhu, Cuiju ;
Zhang, Yuanfei ;
Zhao, Huaiqing ;
Huang, Shijun ;
Zhang, Min ;
Su, Weiping .
ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (2-3) :331-338