Facile and effective approach for oxidation of boronic acids

被引:20
作者
Wagh, Ravindra B. [1 ]
Nagarkar, Jayashree M. [1 ]
机构
[1] Inst Chem Technol, Dept Chem, Mumbai 400019, Maharashtra, India
关键词
Oxidation; Synthetic organic; Boronic acid; Dimethyl carbonate; Peroxides; ARYLBORONIC ACIDS; IPSO-HYDROXYLATION; DIMETHYL CARBONATE; PHENOLIC-COMPOUNDS; SULFIDE COMPOUNDS; ROOM-TEMPERATURE; ARYL HALIDES; CATALYST; MILD; CONVERSION;
D O I
10.1016/j.tetlet.2017.10.059
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This present work illustrates facile and effective approach for oxidation of boronic acids using environmentally benign dimethyl carbonate (DMC) as a solvent with H2O2 as an oxidant at room temperature. In contrast to previous reaction reports, which make use of metal catalyst, hazardous reagent and oxidants that creates environmental concern. This method provides good to excellent yield of products and showed better tolerance towards various functional groups present on boronic acids. Moreover, this developed process is an alternative in terms of inexpensive, non toxic and easy reaction conditions. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4572 / 4575
页数:4
相关论文
共 33 条
[1]   The selective reaction of aryl halides with KOH: Synthesis of phenols, aromatic ethers, and benzofurans [J].
Anderson, Kevin W. ;
Ikawa, Takashi ;
Tundel, Rachel E. ;
Buchwald, Stephen L. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (33) :10694-10695
[2]   Dimethylcarbonate: a modern green reagent and solvent [J].
Arico, F. ;
Tundo, P. .
RUSSIAN CHEMICAL REVIEWS, 2010, 79 (06) :479-489
[3]  
Benjamin R., 2002, EUR J ORG CHEM, V20, P3429
[4]   A Mild and Highly Efficient Conversion of Arylboronic Acids into Phenols by Oxidation with MCPBA [J].
Chen, Dong-Song ;
Huang, Jing-Mei .
SYNLETT, 2013, 24 (04) :499-501
[5]   Hydroboration with pyridine borane at room temperature [J].
Clay, JM ;
Vedejs, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (16) :5766-5767
[6]   Alcohols, ethers and phenols [J].
George, T ;
Mabon, R ;
Sweeney, G ;
Sweeney, JB ;
Tavassoli, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (16) :2529-2574
[7]   A mild and efficient protocol for the ipso-hydroxylation of arylboronic acids [J].
Gogoi, Ankur ;
Bora, Utpal .
TETRAHEDRON LETTERS, 2013, 54 (14) :1821-1823
[8]   An Iodine-Promoted, Mild and Efficient Method for the Synthesis of Phenols from Arylboronic Acids [J].
Gogoi, Ankur ;
Bora, Utpal .
SYNLETT, 2012, (07) :1079-1081
[9]   Boric Acid as Highly Efficient Catalyst for the Synthesis of Phenols from Arylboronic Acids [J].
Gogoi, Kongkona ;
Dewan, Anindita ;
Gogoi, Ankur ;
Borah, Geetika ;
Bora, Utpal .
HETEROATOM CHEMISTRY, 2014, 25 (02) :127-130
[10]   Grafting of Ru(III) complex onto nanosilica and its implication as heterogeneous catalyst for aerobic oxidative hydroxylation of arylboronic acids [J].
Gogoi, Nibedita ;
Gogoi, Pradip K. ;
Borah, Geetika ;
Bora, Utpal .
TETRAHEDRON LETTERS, 2016, 57 (36) :4050-4052