Intermolecular Markovnikov-Selective Hydroacylation of Olefins Catalyzed by a Cationic Ruthenium-Hydride Complex

被引:26
|
作者
Kim, Junghwa [1 ]
Yi, Chae S. [1 ]
机构
[1] Marquette Univ, Dept Chem, Milwaukee, WI 53201 USA
来源
ACS CATALYSIS | 2016年 / 6卷 / 05期
基金
美国国家科学基金会;
关键词
hydroacylation; alkene; aldehyde; ruthenium catalyst; branched ketone; ALDEHYDE OXIDATION LEVEL; C-H ALKYLATION; INTRAMOLECULAR HYDROACYLATION; BETA; GAMMA-UNSATURATED KETONES; ASYMMETRIC CATALYSIS; BOND ACTIVATION; ALCOHOLS; ALKENES; FUNCTIONALIZATION; MECHANISM;
D O I
10.1021/acscatal.6b00856
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The cationic Ru-H complex was found to be an effective catalyst for the intermolecular hydroacylation of aryl-substituted olefins with aldehydes to form branched ketone products. The preliminary kinetic and spectroscopic studies elucidated a ruthenium-acyl complex as the key intermediate species. The catalytic method directly afforded branched ketone products in a highly regioselective manner while tolerating a number of heteroatom functional groups.
引用
收藏
页码:3336 / 3339
页数:4
相关论文
共 50 条
  • [31] Theoretical Studies for Switching Regioselectivity in Ruthenium Hydride-Catalyzed Alkyne Hydroacylation
    Wang, Fen
    Meng, Qingxi
    CHEMISTRYSELECT, 2017, 2 (09): : 2858 - 2865
  • [32] Direct intermolecular hydroacylation of N,N-dialkylacrylamides with aldehydes catalyzed by a cationic rhodium(I)/dppb complex
    Tanaka, Ken
    Shibata, Yu
    Suda, Takeshi
    Hagiwara, Yuji
    Hirano, Masao
    ORGANIC LETTERS, 2007, 9 (07) : 1215 - 1218
  • [33] Intermolecular Dehydrative Coupling Reaction of Aryl Ketones with Cyclic Alkenes Catalyzed by a Well-Defined Cationic Ruthenium-Hydride Complex: A Novel Ketone Olefination Method via Vinyl C-H Bond Activation
    Yi, Chae S.
    Lee, Do W.
    ORGANOMETALLICS, 2010, 29 (08) : 1883 - 1885
  • [34] Homogeneous hydrogenation of alkenes catalyzed by the ruthenium-hydride complex (PCy3)2(CO)(Cl)RuH:: Spectroscopic observation of the ruthenium-ethylene-hydride intermediate species
    Yi, CS
    Lee, DW
    ORGANOMETALLICS, 1999, 18 (24) : 5152 - 5156
  • [35] Nickel-Catalyzed Markovnikov-Selective Hydrodifluoromethylation of Alkynes Using BrCF2H
    Pan, Shiwei
    Chen, Fan
    Zhang, Yanyan
    Shao, Liang
    Chu, Lingling
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (31)
  • [36] Cobalt-catalyzed intermolecular hydroacylation of aldehydes: initiation of hydride transfer enables turnover
    Li, Ting
    Xu, Bao-Hua
    Zhu, De-Ping
    Wang, Yao-Feng
    Zhang, Suo-Jiang
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (12): : 1933 - 1939
  • [37] A theoretical study on the mechanisms of intermolecular hydroacylation of aldehyde catalyzed by neutral and cationic rhodium complexes
    WANG Min
    ZHANG Xin
    CHEN Zhuo
    TANG YanHui
    LEI Ming
    Science China Chemistry, 2014, (09) : 1264 - 1275
  • [38] A theoretical study on the mechanisms of intermolecular hydroacylation of aldehyde catalyzed by neutral and cationic rhodium complexes
    Min Wang
    Xin Zhang
    Zhuo Chen
    YanHui Tang
    Ming Lei
    Science China Chemistry, 2014, 57 : 1264 - 1275
  • [39] A theoretical study on the mechanisms of intermolecular hydroacylation of aldehyde catalyzed by neutral and cationic rhodium complexes
    WANG Min
    ZHANG Xin
    CHEN Zhuo
    TANG YanHui
    LEI Ming
    Science China(Chemistry), 2014, 57 (09) : 1264 - 1275
  • [40] A theoretical study on the mechanisms of intermolecular hydroacylation of aldehyde catalyzed by neutral and cationic rhodium complexes
    Wang Min
    Zhang Xin
    Chen Zhuo
    Tang YanHui
    Lei Ming
    SCIENCE CHINA-CHEMISTRY, 2014, 57 (09) : 1264 - 1275