Synthesis of novel palladacycles and their application in Heck and Suzuki reactions under aerobic conditions

被引：121

作者：

Xiong, ZC

Wang, ND

Dai, MJ

Li, A

Chen, JH

Yang, Z ^{[1
]}

机构：

[1] Coll Chem, Key Lab Bioorgan Chem & Mol Engn, Minist Educ, Beijing 100871, Peoples R China

[2] Peking Univ, Lab Chem Genet, Shenzhen Grad Sch, Shenzhen 518055, Peoples R China

[3] VivoQuest Inc, Valley Cottage, NY 10989 USA

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 19期

关键词：

D O I：

10.1021/ol048749s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Design and synthesis of a novel family of furancarbothioamide-based palladacycles are reported herein. These palladacycles are thermally stable, not sensitive to air or moisture, and are applied effectively in the Heck reaction of aryl halides with terminal olefins and in the Suzuki reaction of aryl halides with arylboronic acids. These reactions were performed under aerobic conditions, leading to turnover numbers (TONs) up to 1 x 10(5).

引用

收藏

页码：3337 / 3340

页数：4

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共 44 条

[21] METAL-COMPLEXES OF N-HETEROCYCLIC CARBENES - A NEW STRUCTURAL PRINCIPLE FOR CATALYSTS IN HOMOGENEOUS CATALYSIS [J].

HERRMANN, WA ;

ELISON, M ;

FISCHER, J ;

KOCHER, C ;

ARTUS, GRJ .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (21) :2371-2374

[22] Application of palladacycles in Heck type reactions [J].

Herrmann, WA ;

Böhm, VPW ;

Reisinger, CP .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 576 (1-2) :23-41

[23] Heck reaction catalyzed by phospha-palladacycles in non-aqueous ionic liquids [J].

Herrmann, WA ;

Böhm, VPW .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 572 (01) :141-145

[24] Palladium-mediated intramolecular carbonylative annulation of o-alkynylphenols to synthesize benzo[b]furo[3,4-d]furan-1-ones [J].

Hu, YH ;

Yang, Z .

ORGANIC LETTERS, 2001, 3 (09) :1387-1390

[25] HIGHLY STEREOSPECIFIC PALLADIUM-CATALYZED VINYLATION OF VINYLIC HALIDES UNDER SOLID-LIQUID PHASE-TRANSFER CONDITIONS [J].

JEFFERY, T .

TETRAHEDRON LETTERS, 1985, 26 (22) :2667-2670

[26] First Heck reaction with arenediazonium cations with recovery of Pd-triolefinic macrocyclic catalyst [J].

Masllorens, J ;

Moreno-Mañas, M ;

Pla-Quintana, A ;

Roglans, A .

ORGANIC LETTERS, 2003, 5 (09) :1559-1561

[27] Donor-functionalized heterocyclic carbene complexes of palladium(II): Efficient catalysts for C-C coupling reactions [J].

McGuinness, DS ;

Cavell, KJ .

ORGANOMETALLICS, 2000, 19 (05) :741-748

[28] Regiospecific carbonylative annulation of iodophenol acetates and acetylenes to construct the flavones by a new catalyst of palladium-thiourea-dppp complex [J].

Miao, H ;

Yang, Z .

ORGANIC LETTERS, 2000, 2 (12) :1765-1768

[29] THIOPHENE RING CYCLOPALLADATION OF N,N-DIMETHYL-2(OR 3)-THIOPHENECARBOTHIOAMIDE [J].

MIZUNO, H ;

NONOYAMA, M .

POLYHEDRON, 1990, 9 (10) :1287-1292

[30] Di-2-pyridylmethylamine-based palladium complexes as new catalysts for Heck, Suzuki, and Sonogashira reactions in organic and aqueous solvents [J].

Nájera, C ;

Gil-Moltó, J ;

Karlstrom, S ;

Falvello, LR .

ORGANIC LETTERS, 2003, 5 (09) :1451-1454

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