Flavin-catalyzed generation of diimide: An environmentally friendly method for the aerobic hydrogenation of olefins

被引:99
作者
Imada, Y [1 ]
Iida, H [1 ]
Naota, T [1 ]
机构
[1] Osaka Univ, Grad Sch Engn Sci, Dept Chem, Toyonaka, Osaka 5608531, Japan
关键词
D O I
10.1021/ja053976q
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The first green and practical method for aerobic hydrogenation" involving the use of hydrazine and an organocatalyst is described. Olefins can be hydrogenated by treatment with hydrazine in the presence of a 5-ethyl-3-methyllumiflavinium perchlorate (FlEt+·ClO4-) catalyst under O2 atmosphere to give the corresponding hydrogenated products in excellent yields along with environmentally benign water and molecular nitrogen as the only waste products. Copyright © 2005 American Chemical Society."
引用
收藏
页码:14544 / 14545
页数:2
相关论文
共 24 条
[1]  
Chaloner P A., 1994, Homogeneous Hydrogenation, DOI [DOI 10.1007/978-94-017-1791-5, 10.1007/978-94-017-1791-5]
[2]   CHEMISTRY OF DIIMIDE .2. STEREOCHEMISTRY OF HYDROGEN TRANSFER TO CARBON-CARBON MULTIPLE BONDS [J].
COREY, EJ ;
PASTO, DJ ;
MOCK, WL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (13) :2957-&
[3]  
COREY EJ, 1961, TETRAHEDRON LETT, V2, P347
[4]   5-BETA, 12-ALPHA-CHOLAJERVANE AND RELATED COMPOUNDS [J].
EBERSOLE, RC ;
CHANG, FC .
JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (15) :2579-2587
[5]   FACTORS DETERMINING NUCLEOPHILIC REACTIVITIES [J].
EDWARDS, JO ;
PEARSON, RG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (01) :16-&
[6]   THE ALPHA EFFECT - ON THE ORIGIN OF TRANSITION-STATE STABILIZATION [J].
HOZ, S .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (18) :3545-3547
[7]   CHEMISTRY OF DIIMINE [J].
HUNIG, S ;
MULLER, HR ;
THIER, W .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1965, 4 (04) :271-&
[8]   An aerobic, organocatalytic, and chemoselective method for Baeyer-Villiger oxidation [J].
Imada, Y ;
Iida, H ;
Murahashi, S ;
Naota, T .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (11) :1704-1706
[9]   Flavin catalyzed oxidations of sulfides and amines with molecular oxygen [J].
Imada, Y ;
Iida, H ;
Ono, S ;
Murahashi, SI .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (10) :2868-2869
[10]   REACTION OF 3O2 WITH DIHYDROFLAVINS .1. "N3,5-DIMETHYL-1,5-DIHYDROLUMIFLAVIN AND 1,5-DIHYDROISOALLOXAZINES [J].
KEMAL, C ;
CHAN, TW ;
BRUICE, TC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (22) :7272-7286