Iridium Complex-Catalyzed C2-Extension of Primary Alcohols with Ethanol via a Hydrogen Autotransfer Reaction

被引：15
|
作者：
Kobayashi, Masaki [1 ]
Itoh, Satoshi [1 ]
Yoshimura, Keisuke [1 ]
Tsukamoto, Yuya [1 ]
Obora, Yasushi [1 ]
机构：
[1] Kansai Univ, Dept Chem & Mat Engn, Fac Chem Mat & Bioengn, Suita, Osaka 5648680, Japan
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 18期
关键词：
ONE-POT SYNTHESIS; ALPHA-ALKYLATION; BORROWING HYDROGEN; CARBOXYLIC-ACIDS; GUERBET REACTION; C-H; KETONES; DEHYDROGENATION; ACTIVATION; SECONDARY;
D O I：
10.1021/acs.joc.0c01540
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The development of a C2-extension of primary alcohols with ethanol as the C2 source and catalysis by [Cp*IrCl2](2) (where Cp* = pentamethylcyclopentadiene) is described. This new extension system was used for a range of benzylic alcohol substrates and for aliphatic alcohols with ethanol as an alkyl reagent to generate the corresponding C2-extended linear alcohols. Mechanistic studies of the reaction by means of intermediates and deuterium labeling experiments suggest the reaction is based on hydrogen autotransfer.
引用
收藏
页码：11952 / 11958
页数：7
相关论文
共 38 条
  • [1] Nickel(II)-NΛNΛO Pincer Type Complex-Catalyzed N-alkylation of Amines with Alcohols via the Hydrogen Autotransfer Reaction
    Balamurugan, Gunasekaran
    Ramesh, Rengan
    Malecki, Jan Grzegorz
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (11): : 7125 - 7135
  • [2] Cobalt-Catalyzed Alkylation of Secondary Alcohols with Primary Alcohols via Borrowing Hydrogen/Hydrogen Autotransfer
    Freitag, Frederik
    Irrgang, Torsten
    Kempe, Rhett
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (50) : 12110 - 12113
  • [3] Iridium complex catalyzed hydrogen transfer reaction of unsaturated alcohols
    LIN Ying-Rui
    MA Da-Wei
    LU Xi-Yan*
    [J]. Chinese Journal of Chemistry, 1988, (03) : 272 - 274
  • [4] Cyclometalated Iridium Complex-Catalyzed N-Alkylation of Amines with Alcohols via Borrowing Hydrogen in Aqueous Media
    Luo, NianHua
    Zhong, YuHong
    Wen, HuiLing
    Luo, Renshi
    [J]. ACS OMEGA, 2020, 5 (42): : 27723 - 27732
  • [5] C-Alkylation of Secondary Alcohols by Primary Alcohols through Manganese-Catalyzed Double Hydrogen Autotransfer
    El-Sepelgy, Osama
    Matador, Esteban
    Brzozowska, Aleksandra
    Rueping, Magnus
    [J]. CHEMSUSCHEM, 2019, 12 (13) : 3099 - 3102
  • [6] IRIDIUM COMPLEX CATALYZED HYDROGEN TRANSFER-REACTION OF UNSATURATED SECONDARY ALCOHOLS
    LIN, YR
    MA, DW
    LU, XY
    [J]. ACTA CHIMICA SINICA, 1988, 46 (01) : 93 - 95
  • [7] Manganese-Catalyzed Hydrogen-Autotransfer C-C Bond Formation: α-Alkylation of Ketones with Primary Alcohols
    Pena-Lopez, Miguel
    Piehl, Patrick
    Elangovan, Saravanakumar
    Neumann, Helfried
    Beller, Matthias
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (48) : 14967 - 14971
  • [8] Direct couplings of secondary alcohols with primary alkenyl alcohols to ?-alkylated ketones via a tandem transfer hydrogenation/hydrogen autotransfer process catalyzed by a metal-ligand bifunctional iridium catalyst
    Xu, Xiangchao
    Li, Shun
    Luo, Shiyuan
    Yang, Jiazhi
    Li, Feng
    [J]. JOURNAL OF CATALYSIS, 2022, 413 : 365 - 373
  • [9] Nickel-catalyzed C-alkylation of thioamide, amides and esters by primary alcohols through a hydrogen autotransfer strategy
    Yang, Peng
    Wang, Xiuhua
    Ma, Yu
    Sun, Yaxin
    Zhang, Li
    Yue, Jieyu
    Fu, Kaiyue
    Zhou, Jianrong Steve
    Tang, Bo
    [J]. CHEMICAL COMMUNICATIONS, 2020, 56 (90) : 14083 - 14086
  • [10] Iridium-CNP complex catalyzed cross-coupling of primary alcohols and secondary alcohols by a borrowing hydrogen strategy
    Wang, Dawei
    Zhao, Keyan
    Yu, Xin
    Miao, Hongyan
    Ding, Yuqiang
    [J]. RSC ADVANCES, 2014, 4 (81): : 42924 - 42929
1234