Electrochemically induced Henry reaction of nitromethane and carbonyl compounds

被引:38
作者
Elinson, Michail N. [1 ]
Ilovaisky, Alexey I. [1 ]
Merkulova, Valentina M. [1 ]
Barba, Fructuoso [2 ]
Batanero, Belen [2 ]
机构
[1] ND Zelinskii Inst Organ Chem, Leninsky Prospect 47, Moscow 119991, Russia
[2] Univ Alcala De Henares, Dept Organ Chem, Madrid 28871, Spain
关键词
electrolysis; electrocatalysis; carbonyl compounds; nitromethane; Henry reaction; beta-nitroalcohols;
D O I
10.1016/j.tet.2008.04.039
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The electrolysis of carbonyl compounds and nitromethane in methanol or in the mixture of methanol and DMF in an undivided cell results in the formation of corresponding beta-nitroalcohols in 60-75% yields. Thus, the simple electrocatalytic system can produce under mild conditions an electrochemically induced Henry reaction. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5915 / 5919
页数:5
相关论文
共 50 条
[1]   NEW AND CONVENIENT SYNTHESIS OF (Z)-HENEICOS-6-EN-11-ONE, THE DOUGLAS-FIR TUSSOCK MOTH (ORGYIA-PSEUDOTSUGATA) SEX-PHEROMONE, AND (Z)-NON-6-EN-2-ONE, THE IMMEDIATE PRECURSOR FOR THE SYNTHESIS OF BREVICOMIN, THE SEX ATTRACTANT OF THE WESTERN PINE-BEETLE DENTROCTONUS-BREVICOMIS [J].
BALLINI, R .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (06) :1419-1421
[2]   Nitroaldol (Henry) reaction catalyzed by Amberlyst A-21 as a far superior heterogeneous catalyst. [J].
Ballini, R ;
Bosica, G ;
Forconi, P .
TETRAHEDRON, 1996, 52 (05) :1677-1684
[3]   A NEW STEREOSELECTIVE SYNTHESIS OF (E)-ALPHA,BETA-UNSATURATED-GAMMA-DICARBONYL COMPOUNDS BY THE HENRY REACTION [J].
BALLINI, R ;
BOSICA, G .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (18) :5466-5467
[4]   Nitroaldol reaction in aqueous media: An important improvement of the Henry reaction [J].
Ballini, R ;
Bosica, G .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (02) :425-427
[5]   CHEMOSELECTIVE SYNTHESIS OF FUNCTIONALIZED CONJUGATED NITROALKENES [J].
BALLINI, R ;
CASTAGNANI, R ;
PETRINI, M .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (07) :2160-2162
[6]  
Bandgar BP, 1996, SYNLETT, P149
[7]  
Brittain R T, 1970, Adv Drug Res, V5, P197
[8]   Synthesis of 2-nitroalkanols by Mg-Al-O-t-Bu hydrotalcite [J].
Choudary, BM ;
Kantam, ML ;
Kavita, B .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2001, 169 (1-2) :193-197
[9]   Efficient nitro-aldol reaction using SmI2:: A new route to nitro alcohols under very mild conditions [J].
Concellon, Jose M. ;
Rodriguez-Solla, Humberto ;
Concellon, Carmen .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (20) :7919-7922
[10]   Oxindole amines from isatin [J].
Conn, WR ;
Lindwall, HG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1936, 58 :1236-1239