HIGHLY SELECTIVE INSERTION INTO AROMATIC C-H BONDS IN RHODIUM(II) TRIPHENYLACETATE-CATALYZED DECOMPOSITION OF ALPHA-DIAZOCARBONYL COMPOUNDS

被引:71
作者
HASHIMOTO, S [1 ]
WATANABE, N [1 ]
IKEGAMI, S [1 ]
机构
[1] TEIKYO UNIV,FAC PHARMACEUT SCI,SAGAMIKO,KANAGAWA 19901,JAPAN
关键词
D O I
10.1039/c39920001508
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Rhodium(II) triphenylacetate, which features a bulky bridging ligand, has been demonstrated to exhibit an exceptionally high order of selectivity for aromatic C-H insertion over aliphatic C-H insertion or cyclopropanation in catalytic decompositions of alpha-diazocarbonyl compounds, thus providing an expedient and general entry to variously substituted indan-2-ones.
引用
收藏
页码:1508 / 1510
页数:3
相关论文
共 13 条
[1]   RHODIUM (II) CATALYZED-REACTIONS OF DIAZO-CARBONYL COMPOUNDS [J].
ADAMS, J ;
SPERO, DM .
TETRAHEDRON, 1991, 47 (10-11) :1765-1808
[2]   CATALYTIC METHODS FOR METAL CARBENE TRANSFORMATIONS [J].
DOYLE, MP .
CHEMICAL REVIEWS, 1986, 86 (05) :919-939
[4]   RHODIUM(II) ACETATE AND NAFION-H CATALYZED DECOMPOSITION OF N-ARYLDIAZOAMIDES - AN EFFICIENT SYNTHESIS OF 2(3H)-INDOLINONES [J].
DOYLE, MP ;
SHANKLIN, MS ;
PHO, HQ ;
MAHAPATRO, SN .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (05) :1017-1022
[5]   PREPARATION OF 3-ACETYL-2-HYDROXYINDOLES VIA RHODIUM CARBENOID AROMATIC C-H INSERTION [J].
ETKIN, N ;
BABU, SD ;
FOOKS, CJ ;
DURST, T .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (03) :1093-1096
[6]   DIRHODIUM(II) TETRA(TRIPHENYLACETATE) - A HIGHLY EFFICIENT CATALYST FOR THE SITE-SELECTIVE INTRAMOLECULAR C-H INSERTION REACTIONS OF ALPHA-DIAZO BETA-KETO-ESTERS [J].
HASHIMOTO, S ;
WATANABE, N ;
IKEGAMI, S .
TETRAHEDRON LETTERS, 1992, 33 (19) :2709-2712
[7]   THE STUDIES OF METAL-ION CATALYZED CARBON-HYDROGEN INSERTION OF ALPHA-ALKOXY-ALPHA'-DIAZOKETONES DERIVED FROM MANDELIC AND LACTIC ACIDS [J].
HON, YS ;
CHANG, RC ;
CHAU, TY .
HETEROCYCLES, 1990, 31 (10) :1745-1750
[8]   INTRAMOLECULAR RHODIUM CARBENOID INSERTIONS INTO AROMATIC C-H BONDS - PREPARATION OF 1-CARBOALKOXY-1,3-DIHYDROBENZO[C]THIOPHENE 2,2-DIOXIDES [J].
HRYTSAK, M ;
ETKIN, N ;
DURST, T .
TETRAHEDRON LETTERS, 1986, 27 (47) :5679-5682
[9]   PREPARATION OF 3-ACETYLBENZOFURAN-2(3H)-ONES AND 3-ACETYLNAPHTHOFURAN-2(3H)-ONES VIA INTRAMOLECULAR RHODIUM CARBENOID INSERTION [J].
HRYTSAK, M ;
DURST, T .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (15) :1150-1151
[10]  
KIRKIACHARIAN BS, 1990, SYNTHESIS-STUTTGART, P815