Aryl Boronic Acid Catalysed Dehydrative Substitution of Benzylic Alcohols for C-O Bond Formation

被引：41
|
作者：
Estopina-Duran, Susana [1 ]
Donnelly, Liam J. [1 ]
Mclean, Euan B. [1 ]
Hockin, Bryony M. [1 ]
Slawin, Alexandra M. Z. [1 ]
Taylor, James E. [1 ,2 ]
机构：
[1] Univ St Andrews, EaStCHEM, Sch Chem, St Andrews KY16 9ST, Fife, Scotland
[2] Univ Bath, Dept Chem, Bath BA2 7AY, Avon, England
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2019年 / 25卷 / 15期
基金：
英国工程与自然科学研究理事会;
关键词：
alcohols; boronic acids; etherification; homogeneous catalysis; substitution; FRIEDEL-CRAFTS REACTIONS; PI-ACTIVATED ALCOHOLS; NUCLEOPHILIC-SUBSTITUTION; ALLYLIC ALCOHOLS; MILD; MITSUNOBU; DERIVATIVES; AMINATION; TRIFLATE; AMINES;
D O I：
10.1002/chem.201806057
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A combination of pentafluorophenylboronic acid and oxalic acid catalyses the dehydrative substitution of benzylic alcohols with a second alcohol to form new C-O bonds. This method has been applied to the intermolecular substitution of benzylic alcohols to form symmetrical ethers, intramolecular cyclisations of diols to form aryl-substituted tetrahydrofuran and tetrahydropyran derivatives, and intermolecular crossed-etherification reactions between two different alcohols. Mechanistic control experiments have identified a potential catalytic intermediate formed between the aryl boronic acid and oxalic acid.
引用
收藏
页码：3950 / 3956
页数：7
相关论文
共 50 条
  • [41] Nucleophilic substitution of ferrocenyl alcohols by cerium ammonium nitrate: C-N, C-S, and C-O bonds formation
    Jiang, Ran
    Zhang, Ying
    Shen, Ye-Chen
    Zhu, Xu
    Xu, Xiao-Ping
    Ji, Shun-Jun
    TETRAHEDRON, 2010, 66 (23) : 4073 - 4078
  • [42] Microwave-assisted aromatic C-O bond formation: A rapid and efficient method for the synthesis of aryl ethers
    Xu, Boyan
    Xue, Jijun
    Zhu, Hanrong
    Li, Ying
    CHEMISTRY LETTERS, 2008, 37 (02) : 202 - 203
  • [43] Benzylic C(sp3)-H Functionalization for C-N and C-O Bond Formation via Visible Light Photoredox Catalysis
    Pandey, Ganesh
    Laha, Ramkrishna
    Singh, Deepak
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (16): : 7161 - 7171
  • [44] Arene Activation at Iridium Facilitates C-O Bond Cleavage of Aryl Ethers
    Miller, Alexander J. M.
    Kaminsky, Werner
    Goldberg, Karen I.
    ORGANOMETALLICS, 2014, 33 (05) : 1245 - 1252
  • [45] Arene activation promotes C-O bond cleavage in aryl alkyl ethers
    Miller, Alexander J. M.
    Goldberg, Karen I.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
  • [46] Unveiling the mechanism of triphos-Ru catalysed C-O bond disconnections in polymers
    Ahrens, Alexander
    Batista, Gabriel Martins Ferreira
    Hammershoj, Hans Christian D.
    Schwibinger, Emil Vincent
    Nova, Ainara
    Skrydstrup, Troels
    NATURE COMMUNICATIONS, 2024, 15 (01)
  • [47] Palladium-catalyzed C-O bond formation: direct synthesis of phenols and aryl/alkyl ethers from activated aryl halides
    Chen, Guoshu
    Chan, Albert S. C.
    Kwong, Fuk Yee
    TETRAHEDRON LETTERS, 2007, 48 (03) : 473 - 476
  • [48] Regiospecific Functionalization of Azacalixaromatics through Copper-Mediated Aryl C-H Activation and C-O Bond Formation
    Wang, Zu-Li
    Zhao, Liang
    Wang, Mei-Xiang
    ORGANIC LETTERS, 2011, 13 (24) : 6560 - 6563
  • [49] C-O Cross-Coupling of Activated Aryl and Heteroaryl Halides with Aliphatic Alcohols
    Maligres, Peter E.
    Li, Jing
    Krska, Shane W.
    Schreier, John D.
    Raheem, Izzat T.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (36) : 9071 - 9074
  • [50] Catalytic formation of C-O bonds by alkene activation:: Lewis acid-cycloisomerisation of olefinic alcohols
    Coulombel, L
    Favier, I
    Duñach, E
    CHEMICAL COMMUNICATIONS, 2005, (17) : 2286 - 2288
12345