Mo(VI)-catalyzed conversion of nitriles to amides with hydrogen peroxide in ethanol

被引:6
作者
Ma, Xiaoyun [1 ]
Liu, Dan [2 ]
Wan, Xiaoyan [1 ]
Zhao, Jun [1 ]
机构
[1] Guizhou Educ Univ, Sch Chem & Mat Sci, Guiyang, Peoples R China
[2] Guizhou Univ, Res & Dev Ctr Fine Chem, Guiyang, Peoples R China
关键词
Amide; nitrile; hydration; hydrogen peroxide; sodium molybdate; CATALYZED OXIDATION; SINGLET OXYGEN; HYDRATION; HYDROLYSIS; GENERATION; COMPLEX; FACILE; MILD;
D O I
10.1080/00397911.2023.2178012
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A method for the preparation of primary amides from nitriles using hydrogen peroxide and a catalytic amount of sodium molybdate in ethanol is described. Using this method, nitriles including aromatic nitriles, aromatic heterocyclic nitriles and aliphatic nitriles were converted into the corresponding amides in moderate to high yields. Electronic and steric effects of substituent have a significant effect on the reactivity of nitrile, nitriles with electron-withdrawing group at the para or meta position show high reactivities and they can be converted into the corresponding amide in good to high yield at room temperature.
引用
收藏
页码:503 / 510
页数:8
相关论文
共 23 条
[11]   THE TRANSFORMATION OF NITRILES INTO AMIDES USING SODIUM PERCARBONATE [J].
KABALKA, GW ;
DESHPANDE, SM ;
WADGAONKAR, PP ;
CHATLA, N .
SYNTHETIC COMMUNICATIONS, 1990, 20 (10) :1445-1451
[12]   CONVERSION OF NITRILES TO AMIDES AND ESTERS TO ACIDS BY THE ACTION OF SODIUM SUPEROXIDE [J].
KORNBLUM, N ;
SINGARAM, S .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (25) :4727-4729
[13]   Strengthening the Combination between Enzymes and Metals in Aqueous Medium: Concurrent Ruthenium-Catalyzed Nitrile Hydration - Asymmetric Ketone Bioreduction [J].
Liardo, Elisa ;
Gonzalez-Fernandez, Rebeca ;
Rios-Lombardia, Nicolas ;
Moris, Francisco ;
Garcia-Alvarez, Joaquin ;
Cadierno, Victorio ;
Crochet, Pascale ;
Rebolledo, Francisca ;
Gonzalez-Sabin, Javier .
CHEMCATCHEM, 2018, 10 (20) :4676-4682
[14]   Environmentally friendly Baeyer-Villiger oxidation with H2O2/nitrile over Mg(OH)2 and MgO [J].
Llamas, Rafael ;
Jimenez-Sanchidrian, Cesar ;
Rafael Ruiz, Jose .
APPLIED CATALYSIS B-ENVIRONMENTAL, 2007, 72 (1-2) :18-25
[15]   EFFICIENT Mo(VI)-CATALYZED HYDRATION OF NITRILE WITH ACETALDOXIME [J].
Ma, Xiaoyun ;
He, Ying ;
Lu, Ming .
SYNTHETIC COMMUNICATIONS, 2014, 44 (04) :474-480
[16]   A mild hydration of nitriles catalysed by copper(II) acetate [J].
Marce, Patricia ;
Lynch, James ;
Blacker, A. John ;
Williams, Jonathan M. J. .
CHEMICAL COMMUNICATIONS, 2016, 52 (07) :1436-1438
[17]  
McMaster L, 1917, J AM CHEM SOC, V39, pA103
[18]   Facile and highly selective conversion of nitriles to amides via indirect acid-catalyzed hydration using TFA or AcOH-H2SO4 [J].
Moorthy, JN ;
Singhal, N .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (05) :1926-1929
[19]   REACTIONS OF HYDROGEN PEROXIDE .7. ALKALI-CATALYZED EPOXIDATION AND OXIDATION USING A NITRILE AS CO-REACTANT [J].
PAYNE, GB ;
WILLIAMS, PH ;
DEMING, PH .
JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (03) :659-&
[20]  
Radziszewski B., 1884, BER, V17, P1289