Copper-Catalyzed Methyl Esterification Reactions via C-C Bond Cleavage

被引:102
作者
Zhu, Yan [1 ]
Yan, Hong [1 ]
Lu, Linhua [1 ]
Liu, Defu [1 ]
Ron, Guangwei [1 ]
Mao, Jincheng [1 ]
机构
[1] Soochow Univ, Key Lab Organ Synth Jiangsu Prov, Coll Chem Chem Engn & Mat Sci, Suzhou 215123, Peoples R China
关键词
BENZYLIC ALCOHOLS; OXIDATIVE ESTERIFICATION; COUPLING REACTIONS; ARYL HALIDES; CARBOXYLIC-ACIDS; ALPHA-DDB; BETA-DDB; ALDEHYDES; ESTERS; ACTIVATION;
D O I
10.1021/jo4016387
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The highly effective synthesis of methyl esters from benzylic alcohols, aldehydes, or acids via copper-catalyzed C-C cleavage from tert-butyl hydroperoxide is reported in this paper for the first time. Our protocol is easily accessible and practical, making it a possible supplement for the traditional way.
引用
收藏
页码:9898 / 9905
页数:8
相关论文
共 60 条
[1]  
Abhilasha Mittal Abhilasha Mittal, 2012, Der Pharmacia Lettre, V4, P1461
[2]   Facile open air oxidation of benzylic alcohols in distilled water by in situ made copper(II) complexes [J].
Ahmad, Jahir Uddin ;
Raisanen, Minna T. ;
Kemell, Marianna ;
Heikkila, Mikko J. ;
Leskela, Markku ;
Repo, Timo .
APPLIED CATALYSIS A-GENERAL, 2012, 449 :153-162
[3]   Multi-functionalization of gallic acid towards improved synthesis of α- and β-DDB [J].
Alam, A ;
Takaguchi, Y ;
Ito, H ;
Yoshida, T ;
Tsuboi, S .
TETRAHEDRON, 2005, 61 (07) :1909-1918
[4]   Hydrosilane and bismuth-accelerated palladium catalyzed aerobic oxidative esterification of benzylic alcohols with air [J].
Bai, Xing-Feng ;
Ye, Fei ;
Zheng, Long-Sheng ;
Lai, Guo-Qiao ;
Xia, Chun-Gu ;
Xu, Li-Wen .
CHEMICAL COMMUNICATIONS, 2012, 48 (68) :8592-8594
[5]  
Chandrasekaran A, 2012, ABSTR PAP AM CHEM S, V244
[6]   Synthesis, separation, and theoretical studies of chiral biphenyl lignans (α- and β-DDB) [J].
Chang, JB ;
Chen, RF ;
Guo, RY ;
Dong, CH ;
Zhao, K .
HELVETICA CHIMICA ACTA, 2003, 86 (06) :2239-2246
[7]   Bu4NI-Catalyzed C-O Bond Formation by Using a Cross-Dehydrogenative Coupling (CDC) Reaction [J].
Chen, Long ;
Shi, Erbo ;
Liu, Zhaojun ;
Chen, Shulin ;
Wei, Wei ;
Li, Hong ;
Xu, Kai ;
Wan, Xiaobing .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (15) :4085-4089
[8]   Reaction of CuI with Dialkyl Peroxides: CuII-Alkoxides, Alkoxy Radicals, and Catalytic C-H Etherification [J].
Gephart, Raymond T., III ;
McMullin, Claire L. ;
Sapiezynski, Nicholas G. ;
Jang, Eun Sil ;
Aguila, Mae Joanne B. ;
Cundari, Thomas R. ;
Warren, Timothy H. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (42) :17350-17353
[9]   Peroxovanadium-catalyzed oxidative esterification of aldehydes [J].
Gopinath, R ;
Barkakaty, B ;
Talukdar, B ;
Patel, BK .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (07) :2944-2947
[10]   A catalytic oxidative esterification of aldehydes using V2O5-H2O2 [J].
Gopinath, R ;
Patel, BK .
ORGANIC LETTERS, 2000, 2 (05) :577-579