Sulfur-containing palladacycles: Efficient phosphine-free catalyst precursors for the Suzuki cross-coupling reaction at room temperature

被引：219

作者：

Zim, D ^{[1
]}

Gruber, AS ^{[1
]}

Ebeling, G ^{[1
]}

Dupont, J ^{[1
]}

Monteiro, AL ^{[1
]}

机构：

[1] UFRGS, Inst Quim, Lab Mol Catalysis, BR-91501970 Porto Alegre, RS, Brazil

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 18期

关键词：

D O I：

10.1021/ol0063048

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyclopalladated compounds derived from the ortho-metalation of benzylic tert-butyl thioethers are excellent catalyst precursors for the Suzuki cross-coupling reaction of aryl bromides and chlorides with phenylboronic acid under mild reaction conditions. A broad range of substrates and functional groups are tolerated in this protocol, and highly catalytic activity is attained.

引用

页码：2881 / 2884

页数：4

共 53 条

[1] Insertion of alkenyl sulfides into a palladium-aryl bond .2. Stabilization of sigma-yl-kS chelates and decomposition reactions through C-S cleavage [J].

Albeniz, AC ;

Espinet, P ;

Lin, YS .

ORGANOMETALLICS, 1996, 15 (23) :5010-5017

[2] Orthopalladated triaryl phosphite complexes as highly active catalysts in biaryl coupling reactions [J].

Albisson, DA ;

Bedford, RB ;

Lawrence, SE ;

Scully, PN .

CHEMICAL COMMUNICATIONS, 1998, (19) :2095-2096

[3] Anionic Pd(0) and Pd(II) intermediates in palladium-catalyzed Heck and cross-coupling reactions [J].

Amatore, C ;

Jutand, A .

ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (05) :314-321

[4] Investigations into ambient temperature biaryl coupling reactions [J].

Anderson, JC ;

Namli, H ;

Roberts, CA .

TETRAHEDRON, 1997, 53 (44) :15123-15134

[5] Highly efficient palladium-catalyzed boronic acid coupling reactions in water: Scope and limitations [J].

Badone, D ;

Baroni, M ;

Cardamone, R ;

Ielmini, A ;

Guzzi, U .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (21) :7170-7173

[6] Palladium/P,O-ligand-catalyzed Suzuki cross-coupling reactions of arylboronic acids and aryl chlorides. Isolation and structural characterization of (P,O)-Pd(dba) complex [J].

Bei, XH ;

Turner, HW ;

Weinberg, WH ;

Guram, AS ;

Petersen, JL .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (18) :6797-6803

[7] PALLADACYCLES AS EFFICIENT CATALYSTS FOR ARYL COUPLING REACTIONS [J].

BELLER, M ;

FISCHER, H ;

HERRMANN, WA ;

OFELE, K ;

BROSSMER, C .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (17) :1848-1849

[8] Tridentate SCS palladium(II) complexes: New, highly stable, recyclable catalysts for the heck reaction [J].

Bergbreiter, DE ;

Osburn, PL ;

Liu, YS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (41) :9531-9538

[9] Microwave-assisted aqueous Suzuki cross-coupling reactions [J].

Blettner, CG ;

König, WA ;

Stenzel, W ;

Schotten, T .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (11) :3885-3890

[10] Ligandless palladium catalyzed reactions of arylboronic acids and sodium tetraphenylborate with aryl halides in aqueous media [J].

Bumagin, NA ;

Bykov, VV .

TETRAHEDRON, 1997, 53 (42) :14437-14450

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