Terpyridine Ruthenium-Catalyzed One-Pot Conversion of Aldehydes into Amides

被引:104
|
作者
Gnanamgari, Dinakar [1 ]
Crabtree, Robert H. [1 ]
机构
[1] Yale Univ, Dept Chem, New Haven, CT 06520 USA
关键词
HIGHLY EFFICIENT; OXO COMPLEXES; ALDOXIMES; ALCOHOLS; OXIDATION; NITRILES; TRANSFORMATION; HYDROGEN; LIGANDS; CYCLOPROPANATION;
D O I
10.1021/om8010678
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
TerpyRu(PPh3)Cl-2 is an efficient catalyst for rearranging aldoximes to amides without the need for chelating phosphines or additives as in prior examples. The catalyst is also useful in converting aldehydes into amides in a one-pot process using NaHCO3 as an additive. A mechanism involving nucleophilic attack of deprotonated oxime on an adjacent nitrile is suggested.
引用
收藏
页码:922 / 924
页数:3
相关论文
共 50 条
  • [1] Ruthenium-catalyzed one-pot synthesis of primary amides from aldehydes in water
    Garcia-Alvarez, Rocio
    Diaz-Alvarez, Alba E.
    Crochet, Pascale
    Cadierno, Victorio
    [J]. RSC ADVANCES, 2013, 3 (17): : 5889 - 5894
  • [2] A ruthenium-catalyzed one-pot method for α-alkylation of ketones with aldehydes
    Cho, Chan Sik
    Shim, Sang Chul
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2006, 691 (20) : 4329 - 4332
  • [3] Palladium-Catalyzed One-Pot Conversion of Aldehydes to Amides
    Ali, Md Ashif
    Punniyamurthy, Tharmalingam
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (2-3) : 288 - 292
  • [4] Facile One-Pot Conversion of Aldehydes into Amides
    Chill, Samuel T.
    Mebane, Robert C.
    [J]. SYNTHETIC COMMUNICATIONS, 2010, 40 (13) : 2014 - 2017
  • [5] A mild general procedure for the one-pot conversion of amides to aldehydes
    Bower, S
    Kreutzer, KA
    Buchwald, SL
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (13-14): : 1515 - 1516
  • [6] Ruthenium-catalyzed one-pot β-alkylation of secondary alcohols with primary alcohols
    Cho, CS
    Kim, BT
    Kim, HS
    Kim, TJ
    Shim, SC
    [J]. ORGANOMETALLICS, 2003, 22 (17) : 3608 - 3610
  • [7] Ruthenium-Catalyzed One-Pot Synthesis of Quinolines from Nitroarenes and Trialkylamines
    Yang, Huiqiong
    Chen, Ru
    Deng, Guojun
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2012, 32 (09) : 1725 - 1731
  • [8] One-pot sequential conversion of aldehydes to N-alkyl hindered amides
    Mebane, Robert
    Cecil, Rebekah
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 251
  • [9] Ruthenium-catalyzed one-pot hydroformylation of alkenes using carbon dioxide as a reactant
    Tominaga, K
    Sasaki, Y
    [J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2004, 220 (02) : 159 - 165
  • [10] Ruthenium(II) carbonyl complexes containing benzhydrazone ligands: synthesis, structure and facile one-pot conversion of aldehydes to amides
    Prabhu, Rupesh Narayana
    Ramesh, Rengan
    [J]. RSC ADVANCES, 2012, 2 (10) : 4515 - 4524