Ruthenium-catalyzed propargylation of aromatic compounds with propargylic alcohols

被引:186
作者
Nishibayashi, Y
Yoshikawa, M
Inada, Y
Hidai, M [1 ]
Uemura, S
机构
[1] Sci Univ Tokyo, Dept Mat Sci & Technol, Noda, Chiba 2788510, Japan
[2] Kyoto Univ, Dept Energy & Hydrocarbon Chem, Sakyo Ku, Kyoto 6068501, Japan
基金
日本科学技术振兴机构;
关键词
D O I
10.1021/ja027023t
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel ruthenium-catalyzed propargylation of aromatic compounds with propargylic alcohols has been found to afford the corresponding propargylated aromatic products in good yields with complete regioselectivity. The catalytic reaction provides a potential usefulness for practical application in organic synthesis, because the selective propargylation of aromatic compounds with an aromatic C-H bond cleavage is generally difficult. Copyright © 2002 American Chemical Society.
引用
收藏
页码:11846 / 11847
页数:2
相关论文
共 25 条
[1]   A THEORETICAL-STUDY OF THE MEYER-SCHUSTER REACTION-MECHANISM - MINIMUM-ENERGY PROFILE AND PROPERTIES OF TRANSITION-STATE STRUCTURE [J].
ANDRES, J ;
CARDENAS, R ;
SILLA, E ;
TAPIA, O .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (03) :666-674
[2]  
Barclay LRC, 1964, FREIDEL CRAFTS REL, VII, P785
[3]   Transition metal complexes containing allenylidene, cumulenylidene, and related ligands [J].
Bruce, MI .
CHEMICAL REVIEWS, 1998, 98 (08) :2797-2858
[4]   Alkenylvinylidene and allenylidene complexes: Evidence for the formation of a metal-trienylidene intermediate [J].
Bruce, MI ;
Hinterding, P ;
Low, PJ ;
Skelton, BW ;
White, AH .
CHEMICAL COMMUNICATIONS, 1996, (09) :1009-1010
[5]  
Cadierno V, 2001, EUR J INORG CHEM, P571
[6]  
CAFFYN AJM, 1995, COMPREHENSIVE ORGANO, V12
[7]   Infrared spectra of C3H3+-N2 dimers:: Identification of proton-bound c-C3H3+-N2 and H2CCCH+-N2 isomers [J].
Dopfer, O ;
Roth, D ;
Maier, JP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (03) :494-502
[8]   MECHANISM OF MEYER-SCHUSTER REARRANGEMENT [J].
EDENS, M ;
BOERNER, D ;
CHASE, CR ;
NASS, D ;
SCHIAVELLI, MD .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (21) :3403-3408
[9]  
Hegedus L.S., 1999, TRANSITION METALS SY, V2nd
[10]   STABLE CARBOCATION .266. STUDY OF C-13-C-13 NMR COUPLING-CONSTANTS IN ALPHA-CYANODIARYLMETHYL AND 1,1-DIARYL-2-BUTYNYL CATIONS [J].
KRISHNAMURTHY, VV ;
PRAKASH, GKS ;
IYER, PS ;
OLAH, GA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (07) :1575-1579