Direct intermolecular hydroacylation of N,N-dialkylacrylamides with aldehydes catalyzed by a cationic rhodium(I)/dppb complex

被引：84
|
作者：
Tanaka, Ken [1 ]
Shibata, Yu
Suda, Takeshi
Hagiwara, Yuji
Hirano, Masao
机构：
[1] Tokyo Univ Agr & Technol, Dept Appl Chem, Grad Sch Engn, Koganei, Tokyo 1848588, Japan
[2] Tokyo Univ Agr & Technol, Instrumentat Anal Ctr, Koganei, Tokyo 1848588, Japan
来源：
ORGANIC LETTERS | 2007年 / 9卷 / 07期
关键词：
D O I：
10.1021/ol070153s
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A cationic rhodium(I)/dppb complex catalyzed direct intermolecular hydroacylation of N,N-dialkylacrylamides with both aliphatic and aromatic aldehydes has been achieved through the stabilization of acylrhodium intermediates by alkene chelation to rhodium. This method represents a versatile new route to gamma-ketoamides in view of the high atom economy and commercial availability of substrates.
引用
收藏
页码：1215 / 1218
页数：4
相关论文
共 50 条
  • [1] A theoretical study on the intermolecular hydroacylation of alkyne catalyzed by cationic rhodium complex
    Chung, LW
    Wu, YD
    JOURNAL OF THEORETICAL & COMPUTATIONAL CHEMISTRY, 2005, 4 : 737 - 749
  • [2] Rhodium (I) catalyzed intermolecular hydroacylation.
    Sapmaz, S
    Willis, MC
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2001, 222 : U59 - U59
  • [3] Rhodium(I)-Catalyzed Intermolecular Hydroacylation of α-Keto Amides and Isatins with Non-Chelating Aldehydes
    Kou, Kevin G. M.
    Longobardi, Lauren E.
    Dong, Vy M.
    ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (10) : 2233 - 2237
  • [4] Mechanism of intermolecular hydroacylation of vinylsilanes catalyzed by a rhodium(I) olefin complex: a DFT study
    Meng, Qingxi
    Shen, Wei
    Li, Ming
    JOURNAL OF MOLECULAR MODELING, 2012, 18 (03) : 1229 - 1239
  • [5] Mechanism of intermolecular hydroacylation of vinylsilanes catalyzed by a rhodium(I) olefin complex: a DFT study
    Qingxi Meng
    Wei Shen
    Ming Li
    Journal of Molecular Modeling, 2012, 18 : 1229 - 1239
  • [6] RUTHENIUM COMPLEX CATALYZED INTERMOLECULAR HYDROACYLATION AND TRANSHYDROFORMYLATION OF OLEFINS WITH ALDEHYDES
    KONDO, T
    AKAZOME, M
    TSUJI, Y
    WATANABE, Y
    JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (04): : 1286 - 1291
  • [7] Rhodium-Catalyzed Highly Enantioselective Direct Intermolecular Hydroacylation of 1,1-Disubstituted Alkenes with Unfunctionalized Aldehydes
    Shibata, Yu
    Tanaka, Ken
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (35) : 12552 - +
  • [8] 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
  • [9] 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
  • [10] 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
12345