The first general palladium catalyst for the Suzuki-Miyaura and carbonyl enolate coupling of aryl arenesulfonates

被引：382

作者：

Nguyen, HN ^{[1
]}

Huang, XH ^{[1
]}

Buchwald, SL ^{[1
]}

机构：

[1] MIT, Dept Chem, Cambridge, MA 02139 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2003年 / 125卷 / 39期

关键词：

D O I：

10.1021/ja036947t

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first general method for the palladium-catalyzed Suzuki-Miyaura and carbonyl enolate coupling of unactivated aryl arenesulfonates was developed utilizing XPhos, 1, and Pd(OAc)2. This is of significant interest because aryl tosylates and aryl benzenesulfonates are more easily handled and considerably less expensive than aryl triflates. This catalyst system effects the coupling of a variety of aryl, heteroaryl, and extremely hindered arylboronic acids with different aryl tosylates, under mild conditions. The same catalyst was employed in the first carbonyl enolate coupling of aryl arensulfonates. Copyright © 2003 American Chemical Society.

引用

收藏

页码：11818 / 11819

页数：2

相关论文

共 29 条

[1] PALLADIUM-CATALYZED COUPLING OF ARYL ARENESULFONATES WITH ORGANOSTANNANES [J].

BADONE, D ;

CECCHI, R ;

GUZZI, U .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (23) :6321-6323

[2]

Bolm C, 2000, SYNTHESIS-STUTTGART, P911

[3] Palladium-catalyzed α-arylation of carbonyl compounds and nitriles [J].

Culkin, DA ;

Hartwig, JF .

ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (04) :234-245

[4]

DIEDRICH F, 1998, METAL CATALYZED CROS

[5] Highly active and selective catalysts for the formation of α-aryl ketones [J].

Fox, JM ;

Huang, XH ;

Chieffi, A ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (07) :1360-1370

[6] First examples of a tosylate in the palladium-catalyzed Heck cross coupling reaction [J].

Fu, XY ;

Zhang, SY ;

Yin, JG ;

McAllister, TL ;

Jiang, SA ;

Tann, CH ;

Thiruvengadam, TK ;

Zhang, FC .

TETRAHEDRON LETTERS, 2002, 43 (04) :573-576

[7] A copper-free palladium catalyzed cross coupling reaction of vinyl tosylates with terminal acetylenes [J].

Fu, XY ;

Zhang, SY ;

Yin, JG ;

Schumacher, DP .

TETRAHEDRON LETTERS, 2002, 43 (37) :6673-6676

[8] Iron-catalyzed cross-coupling reactions [J].

Fürstner, A ;

Leitner, A ;

Méndez, M ;

Krause, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (46) :13856-13863

[9] Sterically hindered chelating alkyl phosphines provide large rate accelerations in palladium-catalyzed amination of aryl iodides, bromides, and chlorides, and the first amination of aryl tosylates [J].

Hamann, BC ;

Hartwig, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (29) :7369-7370

[10] Expanding Pd-catalyzed C-N bond-forming processes: The first amidation of aryl sulfonates, aqueous amination, and complementarity with Cu-catalyzed reactions [J].

Huang, XH ;

Anderson, KW ;

Zim, D ;

Jiang, L ;

Klapars, A ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (22) :6653-6655