Iridium-catalyzed reductive etherification of α,β-unsaturated ketones and aldehydes with alcohols

被引：12
|
作者：
Ouyang, Lu [1 ]
Xia, Yanping [1 ]
Miao, Rui [1 ]
Liao, Jianhua [1 ]
Luo, Renshi [1 ]
机构：
[1] Gannan Med Univ, Sch Pharm, Ganzhou 341000, Jiangxi, Peoples R China
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2022年 / 20卷 / 13期
基金：
中国国家自然科学基金;
关键词：
CHEMOSELECTIVE TRANSFER HYDROGENATION; CARBONYL-COMPOUNDS; C-O; SYMMETRICAL ETHERS; SILANE REDUCTIONS; GENERAL-SYNTHESIS; SYNTHETIC METHODS; ACIDIC MEDIA; SECONDARY; METHANOL;
D O I：
10.1039/d2ob00122e
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An iridium complex-catalyzed reductive etherification of alpha,beta-unsaturated ketones and aldehydes with primary alcohols is presented, affording allyl ethers in excellent yields. Deuterated and control experiments showed that this etherification transformation proceeded through a cascade transfer hydrogenation and alcohol condensation process. Moreover, the utility of this protocol is evidenced by the gram-scale performance.
引用
收藏
页码：2621 / 2625
页数：5
相关论文
共 50 条
  • [1] Iridium-catalyzed enantioselective reductive amination of aromatic ketones
    Liu, Ruixia
    Li, Bin
    Han, Jingkuo
    Zhang, Dongxu
    Li, Muqiong
    Yao, Lin
    Zhao, Wei
    Wang, Qiaofeng
    Jiang, Ru
    Nie, Huifang
    CATALYSIS SCIENCE & TECHNOLOGY, 2020, 10 (16) : 5448 - 5452
  • [2] Ru(dppbsa)-catalyzed hydrodeoxygenation and reductive etherification of ketones and aldehydes
    Sun, Rui
    Hon-Yu Guo
    Shuang-Shuang Ma
    Yao-Feng Wang
    Zheng-Kun Yu
    Bao-Hua Xu
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (07): : 1943 - 1954
  • [3] Mechanistic Insights into the Iridium-Catalyzed Hydrogenations of α,β-Unsaturated Ketones
    Engel, Julien
    Mersmann, Stefanie
    Norrby, Per-Ola
    Bolm, Carsten
    CHEMCATCHEM, 2016, 8 (19) : 3099 - 3106
  • [4] Direct, iridium-catalyzed enantioselective and regioselective allylic etherification with aliphatic alcohols
    Ueno, Satoshi
    Hartwig, John F.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (10) : 1928 - 1931
  • [5] Iridium-catalyzed direct asymmetric reductive amination of aromatic ketones
    Huang, Haizhou
    Wu, Zitong
    Gao, Guorui
    Zhou, Le
    Chang, Mingxin
    ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (10): : 1976 - 1980
  • [6] Cobalt/Lewis acid cooperative catalysis for reductive etherification of ketones and aldehydes with alcohols
    Liu, Bingxue
    Li, Yibiao
    Liu, Qiang
    CHEM CATALYSIS, 2022, 2 (04): : 883 - 897
  • [7] Iridium-catalyzed chemoselective transfer hydrogenation of α, β-unsaturated ketones to saturated ketones in water
    Jiang, Xiaolan
    Cui, Xiaofeng
    Chen, Jinxun
    Liu, Qixing
    Chen, Yongsheng
    Zhou, Haifeng
    TETRAHEDRON LETTERS, 2022, 90
  • [8] Iridium-catalyzed asymmetric reductive amination of ketones using an amidophosphite ligand
    S. E. Lyubimov
    D. V. Ozolin
    P. Yu. Ivanov
    K. B. Maiorov
    V. S. Velezheva
    V. A. Davankov
    Russian Chemical Bulletin, 2015, 64 : 318 - 321
  • [9] Iridium-catalyzed asymmetric reductive amination of ketones using an amidophosphite ligand
    Lyubimov, S. E.
    Ozolin, D. V.
    Ivanov, P. Yu.
    Maiorov, K. B.
    Velezheva, V. S.
    Davankov, V. A.
    RUSSIAN CHEMICAL BULLETIN, 2015, 64 (02) : 318 - 321
  • [10] Iridium-Catalyzed Alkylation of Secondary Alcohols with Primary Alcohols: A Route to Access Branched Ketones and Alcohols
    Genc, Sertac
    Gulcemal, Suleyman
    Gunnaz, Salih
    Cetinkaya, Bekir
    Gulcemal, Derya
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (14): : 9139 - 9152
12345