Indium as a reducing agent.: Chemoselective reduction of α-halocarbonyl compounds and benzyl halides by indium metal in water under sonication

被引:48
作者
Ranu, BC [1 ]
Dutta, P [1 ]
Sarkar, A [1 ]
机构
[1] Indian Assoc Cultivat Sci, Dept Organ Chem, Calcutta 700032, W Bengal, India
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1999年 / 09期
关键词
D O I
10.1039/a901493d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Indium metal in water reduces a-halocarbonyl compounds and benzyl iodides to the corresponding dehalogenated products in excellent yields under sonication although simple alkyl and aryl iodides remained inert under these conditions.
引用
收藏
页码:1139 / 1140
页数:2
相关论文
共 20 条
[1]   Stereodivergent allylindation of cyclopropenes. Remarkable stereodirection and acceleration by neighbouring carboxyl and hydroxyl groups [J].
Araki, S ;
Nakano, H ;
Subburaj, K ;
Hirashita, T ;
Shibutani, K ;
Yamamura, H ;
Kawai, M ;
Butsugan, Y .
TETRAHEDRON LETTERS, 1998, 39 (35) :6327-6330
[2]   CARBOINDATION OF ALKYNES - REGIOSELECTIVE AND STEREOSELECTIVE ALLYLATION OF CARBON-CARBON TRIPLE BONDS OF ALKYNOLS BY ALLYLIC INDIUM REAGENTS [J].
ARAKI, S ;
IMAI, A ;
SHIMIZU, K ;
YAMADA, M ;
MORI, A ;
BUTSUGAN, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (06) :1841-1847
[3]   Indium mediated intramolecular carbocyclization in aqueous media. A facile and stereoselective synthesis of fused alpha-methylene-gamma-butyrolactones [J].
Bryan, VJ ;
Chan, TH .
TETRAHEDRON LETTERS, 1996, 37 (30) :5341-5342
[4]   Indium-promoted preparation of substituted α-methylene-γ-lactones from 2-(bromomethyl)acrylic acid and carbonyl compounds [J].
Choudhury, PK ;
Foubelo, F ;
Yus, M .
TETRAHEDRON LETTERS, 1998, 39 (21) :3581-3584
[5]  
CINTAS P, 1995, SYNLETT, P1087
[6]   NOVEL FREE-RADICAL RING-EXPANSION REACTIONS [J].
DOWD, P ;
CHOI, SC .
TETRAHEDRON, 1989, 45 (01) :77-90
[7]   Allylation of unactivated and/or functionalized alkynes with allylindiums [J].
Fujiwara, N ;
Yamamoto, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (08) :2318-2319
[8]   Experimental test of setting three contiguous stereogenic centers in water. Diastereoselective coupling of geometrically biased allylic bromides to alpha-oxy aldehydes with indium [J].
Isaac, MB ;
Paquette, LA .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (16) :5333-5338
[9]  
JONES GCL, 1998, SYUNLETT, P903
[10]  
Li C. -J., 1997, ORGANIC REACTIONS AQ