A ruthenium-catalyzed reaction of aromatic ketones with arylboronates: A new method for the arylation of aromatic compounds via C-H bond cleavage

被引：328

作者：

Kakiuchi, F ^{[1
]}

Kan, S ^{[1
]}

Igi, K ^{[1
]}

Chatani, N ^{[1
]}

Murai, S ^{[1
]}

机构：

[1] Osaka Univ, Dept Appl Chem, Fac Engn, Suita, Osaka 5650871, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2003年 / 125卷 / 07期

关键词：

D O I：

10.1021/ja029273f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The ruthenium-catalyzed reaction of aromatic ketones with arylboronic acid esters (arylboronates) gave the ortho arylation product. For this coupling reaction, a RuH2(CO)(PPh3)3 complex exhibited the highest catalytic activity among the complexes screened. Several aromatic ketones, for example, acetophenones, acetonaphthone, α-tetralone, and benzosuberone, can be used in this coupling reaction. A variety of arylboronates containing electron-donating (OMe and NMe2) and -withdrawing (F and CF3) groups were found to react with aromatic ketones to give the corresponding aylation products. The corresponding arylboronic acids could be used in this coupling reaction, but the yields were slightly lower, as compared to those of the reaction using the corresponding arylboronates. Copyright © 2003 American Chemical Society.

引用

页码：1698 / 1699

页数：2

共 42 条

[1] Iridium(I)-catalyzed asymmetric intermolecular hydroarylation of norbornene with benzamide
Aufdenblatten, R
Diezi, S
Togni, A
[J]. MONATSHEFTE FUR CHEMIE, 2000, 131 (12): : 1345 - 1350
[2] ORGANOBORANES .53. A HIGH-FIELD VARIABLE-TEMPERATURE H-1 AND B-11 NMR-STUDY OF THE EFFECTS OF SOLVENT AND STRUCTURE ON REACTIVITY IN ALLYLBORATION
BROWN, HC
RACHERLA, US
PELLECHIA, PJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (06) : 1868 - 1874
[3] Convenient preparation of mononuclear and dinuclear ruthenium hydride complexes for catalytic application
Busch, S
Leitner, W
[J]. CHEMICAL COMMUNICATIONS, 1999, (22) : 2305 - 2306
[4] Ru3(CO)12-catalyzed C-H/CO/olefin coupling of N-pyridylindolines.: Direct carbonylation at a C-H bond δ to the pyridine nitrogen
Chatani, N
Yorimitsu, S
Asaumi, T
Kakiuchi, F
Murai, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (21) : 7557 - 7560
[5] Ru-3(CO)(12)-catalyzed reaction of pyridylbenzenes with carbon monoxide and olefins. Carbonylation at a C-H bond in the benzene ring
Chatani, N
Ie, Y
Kakiuchi, F
Murai, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (08) : 2604 - 2610
[6] Carbonylation at sp3 C-H bonds adjacent to a nitrogen atom in alkylamines catalyzed by rhodium complexes
Chatani, N
Asaumi, T
Ikeda, T
Yorimitsu, S
Ishii, Y
Kakiuchi, F
Murai, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (51) : 12882 - 12883
[7] Ru-3(CO)(12)-catalyzed coupling of heteroaromatic C-H/CO/olefins. Regioselective acylation of the imidazole ring
Chatani, N
Fukuyama, T
Kakiuchi, F
Murai, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (02) : 493 - 494
[8] Ru3(CO)12- and Rh4(CO)12-catalyzed reactions of pyridylolefins or N-(2-pyridyl)enamines with CO and olefins.: Carbonylation at olefinic C-H bonds
Chatani, N
Ishii, Y
Ie, Y
Kakiuchi, F
Murai, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (15) : 5129 - 5136
[9] Durr U, 1997, SYNLETT, P1335
[10] Dyker G, 1999, ANGEW CHEM INT EDIT, V38, P1699, DOI 10.1002/(SICI)1521-3773(19990614)38:12<1698::AID-ANIE1698>3.0.CO

← 1 2 3 4 5 →