IPSO-Hydroxylation of Boronic Acid via Ozonolysis: A Metal-, Ligand-, and Base-free Method

被引:18
作者
Bommegowda, Yadaganahalli K. [1 ]
Mallesha, Ningegowda [2 ]
Vinayaka, Ajjampura C. [1 ]
Sadashiva, Maralinganadoddi P. [1 ]
机构
[1] Univ Mysore, Dept Studies Chem, Mysuru, Karnataka, India
[2] R&D Ctr, Sri Ram Chem, Spl-52,Hebbal Ind Estate, Mysuru, Karnataka, India
关键词
Alcohol; Boronic acid; Ozonolysis; ARYLBORONIC ACIDS; FREE OXIDATION; PHENOLS; CONVERSION; MILD; MECHANISMS; ESTERS;
D O I
10.1246/cl.151087
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Here, we have developed a simple, efficient, and metal-, ligand-, and base-free method for the synthesis of functionalized aryl and alicyclic alcohols via ozonolysis of corresponding boronic acids in aqueous ethanol. The procedure is compatible with a variety of functional groups and can be utilized as an alternative method for the synthesis of hydroxy arenes and alicyclic alcohols.
引用
收藏
页码:268 / 270
页数:3
相关论文
共 29 条
[1]   AUTOXIDATION OF BIOLOGICAL MOLECULES .4. MAXIMIZING THE ANTIOXIDANT ACTIVITY OF PHENOLS [J].
BURTON, GW ;
DOBA, T ;
GABE, EJ ;
HUGHES, L ;
LEE, FL ;
PRASAD, L ;
INGOLD, KU .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (24) :7053-7065
[2]  
Chandel M., 2014, J ENV OCCUP SCI, V3, P204, DOI [10.5455/jeos.20140929042630, DOI 10.5455/JEOS.20140929042630]
[3]  
de la Lastra CA, 2005, MOL NUTR FOOD RES, V49, P405
[4]   C-H Functionalization at Sterically Congested Positions by the Platinum-Catalyzed Borylation of Arenes [J].
Furukawa, Takayuki ;
Tobisu, Mamoru ;
Chatani, Naoto .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (38) :12211-12214
[5]   SILVER-ASSISTED REACTIONS OF ORGANOTIN OXIDES - A MILD, NEUTRAL AND ANHYDROUS ONE-STEP CONVERSION OF PRIMARY ORGANIC HALIDES TO ALCOHOLS [J].
GINGRAS, M ;
CHAN, TH .
TETRAHEDRON LETTERS, 1989, 30 (03) :279-282
[6]   A mild and efficient protocol for the ipso-hydroxylation of arylboronic acids [J].
Gogoi, Ankur ;
Bora, Utpal .
TETRAHEDRON LETTERS, 2013, 54 (14) :1821-1823
[7]   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
[8]   Naturally Occurring Phenolic Antibacterial Compounds Show Effectiveness against Oral Bacteria by a Quantitative Structure-Activity Relationship Study [J].
Greenberg, Michael ;
Dodds, Michael ;
Tian, Minmin .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2008, 56 (23) :11151-11156
[9]   Base-Promoted, Mild and Highly Efficient Conversion of Arylboronic Acids into Phenols with tert-Butyl Hydroperoxide [J].
Guo, Shengmei ;
Lu, Lin ;
Cai, Hu .
SYNLETT, 2013, 24 (13) :1712-1714
[10]   Sandmeyer reactions. Part 7. An investigation into the reduction steps of Sandmeyer hydroxylation and chlorination reactions [J].
Hanson, P ;
Jones, JR ;
Taylor, AB ;
Walton, PH ;
Timms, AW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 2002, (06) :1135-1150