Lanthanum(III) Isopropoxide Catalyzed Chemoselective Transesterification of Dimethyl Carbonate and Methyl Carbamates

被引:42
|
作者
Hatano, Manabu [1 ]
Kamiya, Sho [1 ]
Moriyama, Katsuhiko [1 ]
Ishihara, Kazuaki [1 ,2 ]
机构
[1] Nagoya Univ, Grad Sch Engn, Chikusa Ku, Nagoya, Aichi 4648603, Japan
[2] CREST, Japan Sci & Technol Agcy JST, Chikusa Ku, Nagoya, Aichi 4648603, Japan
关键词
TETRANUCLEAR-ZINC-CLUSTER; TERT-BUTYL ESTERS; LANTHANOID TRI-2-PROPOXIDES; INTERCHANGE REACTION; CARBOXYLIC ESTERS; EFFICIENT METHOD; ALCOHOLS; ESTERIFICATION; MILD; METHANOLYSIS;
D O I
10.1021/ol102754y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A practical transesterification of less reactive dimethyl carbonate and much less reactive methyl carbamates with primary (1 degrees), secondary (2 degrees), and tertiary (3 degrees) alcohols was established with the use of a lanthanum(III) complex, which was prepared in situ from lanthanum(III) isopropoxide (3 mol %) and 2-(2-methoxyethoxy)ethanol (6 mol %). In particular, corresponding carbonates and carbamates obtained were of synthetic utility from the viewpoint of the selective protection and/or deprotection of 1 degrees-, 2 degrees-, and 3 degrees-alcohols.
引用
收藏
页码:430 / 433
页数:4
相关论文
共 50 条
  • [1] Lanthanum Oxide-catalyzed Transesterification of Dimethyl Carbonate with Glycerol: Effect of Surfactant
    Lim, Seung Rok
    Lee, Sang Deuk
    Kim, Hoon Sik
    Simanjuntak, Fidelis Stefanus Hubertson
    Lee, Hyunjoo
    [J]. BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2014, 35 (11): : 3163 - 3168
  • [2] Ligand-Assisted Rate Acceleration in Lanthanum(III) Isopropoxide Catalyzed Transesterification of Carboxylic Esters
    Hatano, Manabu
    Furuya, Yoshiro
    Shimmura, Takumi
    Moriyama, Katsuhiko
    Kamiya, Sho
    Maki, Toshikatsu
    Ishihara, Kazuaki
    [J]. ORGANIC LETTERS, 2011, 13 (03) : 426 - 429
  • [3] Lanthanum(III) catalysts for highly efficient and chemoselective transesterification
    Hatano, Manabu
    Ishihara, Kazuaki
    [J]. CHEMICAL COMMUNICATIONS, 2013, 49 (20) : 1983 - 1997
  • [4] Chemoselective synthesis of asymmetrical carbonate from alcohol and dimethyl carbonate catalyzed by ytterbium(III) triflate
    Yu, Chuanming
    Zhou, Baocheng
    Su, Weike
    Xu, Zhenyuan
    [J]. SYNTHETIC COMMUNICATIONS, 2007, 37 (4-6) : 645 - 651
  • [5] KF/MgO catalyzed transesterification of glycerol and dimethyl carbonate to glycerol carbonate
    Chen, Danyang
    Zhu, Jianyu
    Wu, Qin
    Wang, Ziqing
    Zhang, Jinli
    [J]. Huagong Jinzhan/Chemical Industry and Engineering Progress, 2022, 41 (04): : 2082 - 2089
  • [6] Transesterification of dimethyl carbonate and phenol to diphenyl carbonate catalyzed by titanocene complexes
    Niu Hong-Ying
    Guo Hai-Ming
    Yao Jie
    Wang Yue
    Wang Gong-Ying
    [J]. ACTA CHIMICA SINICA, 2006, 64 (12) : 1269 - 1272
  • [7] Transesterification of dimethyl carbonate and phenol to diphenyl carbonate catalyzed by samariurn diiodide
    Niu, Hongying
    Guo, Haiming
    Yao, He
    Wang, Yue
    Wang, Gongying
    [J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2006, 259 (1-2) : 292 - 295
  • [8] Transesterification of dimethyl carbonate and phenol to diphenyl carbonate catalyzed by titanocene complexes
    Niu, Hongying
    Yao, Jie
    Wang, Yue
    Wang, Gongying
    [J]. CATALYSIS COMMUNICATIONS, 2007, 8 (03) : 355 - 358
  • [9] Production of dimethyl carbonate via alkylene carbonate transesterification catalyzed by basic salts
    De Filippis, P
    Scarsella, M
    Borgianni, C
    Pochetti, F
    [J]. ENERGY & FUELS, 2006, 20 (01) : 17 - 20
  • [10] Transesterification of Dimethyl Carbonate with Ethanol Catalyzed by Guanidine: A Theoretical Analysis
    Gilassi, Sina
    Kaliaguine, Serge
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (10): : 7004 - 7019