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

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2004年 / 126卷 / 09期

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

页码：2706 / 2707

页数：2

共 21 条

[11] ACTIVATION OF CARBON FLUORINE BONDS BY METAL-COMPLEXES [J].

KIPLINGER, JL ;

RICHMOND, TG ;

OSTERBERG, CE .

CHEMICAL REVIEWS, 1994, 94 (02) :373-431

[12]

Miura M, 2002, TOP CURR CHEM, V219, P211

[13] CATALYTIC C-H OLEFIN COUPLING [J].

MURAI, S ;

KAKIUCHI, F ;

SEKINE, S ;

TANAKA, Y ;

KAMATANI, A ;

SONODA, M ;

CHATANI, N .

PURE AND APPLIED CHEMISTRY, 1994, 66 (07) :1527-1534

[14]

Murakami M., 1999, TOP ORGANOMETAL CHEM, V3, P97, DOI DOI 10.1007/3-540-68525-1_5

[15]

RICHMOND TG, 1999, TOPICS ORGANOMETALLI, V3, P233

[16] Ru-, Rh-, and Pd-catalyzed C-C bond formation involving C-H activation and addition on unsaturated substrates: Reactions and mechanistic aspects [J].

Ritleng, V ;

Sirlin, C ;

Pfeffer, M .

CHEMICAL REVIEWS, 2002, 102 (05) :1731-1769

[17]

Rybtchinski B, 1999, ANGEW CHEM INT EDIT, V38, P870, DOI 10.1002/(SICI)1521-3773(19990401)38:7<870::AID-ANIE870>3.0.CO

[18]

2-3

[19] Alkyl- and aryl-oxygen bond activation in solution by rhodium(I), palladium(II), and nickel(II). Transition-metal-based selectivity [J].

van der Boom, ME ;

Liou, SY ;

Ben-David, Y ;

Shimon, LJW ;

Milstein, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (26) :6531-6541

[20] NICKEL-INDUCED CONVERSION OF CARBON-OXYGEN INTO CARBON-CARBON BONDS - ONE-STEP TRANSFORMATIONS OF ENOL ETHERS INTO OLEFINS AND ARYL ETHERS INTO BIARYLS [J].

WENKERT, E ;

MICHELOTTI, EL ;

SWINDELL, CS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (08) :2246-2247

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