Room-temperature Cannizzaro reaction under mild conditions facilitated by magnesium bromide ethyl etherate and triethylamine

被引:48
作者
Abaee, MS [1 ]
Sharifi, R [1 ]
Mojtahedi, MM [1 ]
机构
[1] Chem & Chem Engn Res Ctr Iran, Organ Chem Lab, Tehran, Iran
关键词
D O I
10.1021/ol052506y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A room-temperature convenient Cannizzaro reaction prompted by magnesium bromide ethyl etherate and triethylamine is described for smooth conversion of aromatic aldehydes into their respective alcohols, and carboxylic acids. The methodology is applicable to both inter- and intramolecular reactions and could be directed to obtain the carboxylic moiety in the form of an acid, an amide, or an ester compound depending on the selected reaction conditions or workup procedure.
引用
收藏
页码:5893 / 5895
页数:3
相关论文
共 33 条
[1]   First highly efficient synthesis of bis(arylmethylidene)pyranones mediated by lithium perchlorate [J].
Abaee, MS ;
Mojtahedi, MM ;
Zahedi, MM ;
Bolourtchian, SM .
SYNTHETIC COMMUNICATIONS, 2006, 36 (02) :199-206
[2]   An efficient and improved method for the synthesis of bis(arylmethylidene)thiopyranones [J].
Abaee, MS ;
Mojtahedi, MM ;
Zahedi, MM .
SYNLETT, 2005, (15) :2317-2320
[3]   INTRAMOLECULAR CATALYSIS .4. THE INTRAMOLECULAR CANNIZZARO REACTION OF BIPHENYL-2,2'-DICARBALDEHYDE, [ALPHA,ALPHA'-(H-2)2]BIPHENYL-2,2'-DICARBALDEHYDE AND 4,4' OR 5,5' OR 6,6'-DISUBSTITUTED BIPHENYL-2,2'-DICARBALDEHYDES [J].
ABBASZADEH, MR ;
BOWDEN, K .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1990, (12) :2081-2087
[4]   INTRAMOLECULAR CATALYSIS .5. THE INTRAMOLECULAR CANNIZZARO REACTION OF ORTHO-PHTHALALDEHYDE AND [ALPHA,ALPHA'-H-2(2)]-ORTHO-PHTHALALDEHYDE [J].
BOWDEN, K ;
ELKAISSI, FA ;
RANSON, RJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1990, (12) :2089-2092
[5]   INTRAMOLECULAR CATALYSIS .8. THE INTRAMOLECULAR CANNIZZARO REACTION OF NAPHTHALENE-1,8-DICARBALDEHYDE AND [ALPHA,ALPHA'-(H-2)2]NAPHTHALENE-1,8-DICARBALDEHYDE [J].
BOWDEN, K ;
BUTT, AM ;
STREATER, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1992, (04) :567-571
[6]  
Cannizzaro S., 1853, LIEBIGS ANN CHEM, V88, P129
[7]  
CHANDRASEKHAR S, 1995, J CHEM RES-S, P170
[8]   Ytterbium triflate-promoted tandem one-pot oxidation-Cannizzaro reaction of aryl methyl ketones [J].
Curini, M ;
Epifano, F ;
Genovese, S ;
Marcotullio, MC ;
Rosati, O .
ORGANIC LETTERS, 2005, 7 (07) :1331-1333
[9]  
ELNIMR AE, 1983, PHARMAZIE, V38, P728
[10]   Phase-transfer catalysis and ultrasonic waves I. Cannizzaro reaction [J].
Entezari, MH ;
Shameli, AA .
ULTRASONICS SONOCHEMISTRY, 2000, 7 (04) :169-172