Ruthenium-catalyzed functionalization of aryl carbon-oxygen bonds in aromatic ethers with organoboron compounds

被引:231
作者
Kakiuchi, F [1 ]
Usui, M
Ueno, S
Chatani, N
Murai, S
机构
[1] Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan
[2] JST, PRESTO, Kawaguchi, Saitama, Japan
关键词
D O I
10.1021/ja0393170
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The ruthenium-catalyzed reaction of aryl ethers having a carbonyl group at the ortho position to the ether group with organoboronates (R?B(OCH2CMe2CH2O), R = aryl, alkenyl, and alkyl) resulted in site-selective C?C bond formation. Among the transition metal complexes screened, the RuH2(CO)(PPh3)3 complex showed the highest activity. Several aromatic ketones having methoxy or phenoxy groups at the ortho position can also be used in this coupling reaction. A variety of arylboronates containing electron-donating (NMe2, OMe, methyl, and vinyl) and -withdrawing (F and CF3) groups reacted with methoxy ketones to give the corresponding coupling products in high yields. Copyright © 2004 American Chemical Society.
引用
收藏
页码:2706 / 2707
页数:2
相关论文
共 21 条
[1]   Bond dissociation energies of organic molecules [J].
Blanksby, SJ ;
Ellison, GB .
ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (04) :255-263
[2]  
Guari Y, 1999, EUR J INORG CHEM, P1047
[3]   Rhodium-catalyzed Si-F exchange reaction between fluorobenzenes and a disilane. Catalytic reaction involving cleavage of C-F bonds [J].
Ishii, Y ;
Chatani, N ;
Yorimitsu, S ;
Murai, S .
CHEMISTRY LETTERS, 1998, (02) :157-158
[4]  
Jun CH, 2002, CHEM-EUR J, V8, P2423, DOI 10.1002/1521-3765(20020603)8:11<2422::AID-CHEM2422>3.0.CO
[5]  
2-B
[6]   Catalytic methods for C-H bond functionalization: Application in organic synthesis [J].
Kakiuchi, F ;
Chatani, N .
ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (9-10) :1077-1101
[7]   A ruthenium-catalyzed reaction of aromatic ketones with arylboronates: A new method for the arylation of aromatic compounds via C-H bond cleavage [J].
Kakiuchi, F ;
Kan, S ;
Igi, K ;
Chatani, N ;
Murai, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (07) :1698-1699
[8]   Catalytic C-H/olefin coupling [J].
Kakiuchi, F ;
Murai, S .
ACCOUNTS OF CHEMICAL RESEARCH, 2002, 35 (10) :826-834
[9]   CATALYTIC ADDITION OF AROMATIC CARBON-HYDROGEN BONDS TO OLEFINS WITH THE AID OF RUTHENIUM COMPLEXES [J].
KAKIUCHI, F ;
SEKINE, S ;
TANAKA, Y ;
KAMATANI, A ;
SONODA, M ;
CHATANI, N ;
MURAI, S .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1995, 68 (01) :62-83
[10]  
Kakiuchi F., 1999, TOPICS ORGANOMETALLI, V3, P47, DOI DOI 10.1007/3-540-68525-1-3