Palladium-catalyzed alkynylcarbonylation of aryl iodides with the use of Mo(CO)6 in the presence of tBu3P ligand

被引：56

作者：

Iizuka, Muneaki ^{[1
]}

Kondo, Yoshinori ^{[1
]}

机构：

[1] Tohoku Univ, Grad Sch Pharmaceut Sci, Sendai, Miyagi 9808578, Japan

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 2007卷 / 31期

关键词：

alkynylcarbonylation; palladium; molybdenum; aryl iodides; phosphane ligands;

D O I：

10.1002/ejoc.200700700

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Palladium-catalyzed alkynylcarbonylation of aryl iodides was accomplished by using MO(CO)6 as a CO source. The reaction was conducted at room temperature with the use of tBu(3)P as a ligand, which was found to be essential for smooth carbonylation. One-pot construction of pyrazoles by using aryl iodides with electron-withdrawing groups was also accomplished under these reaction conditions in the presence of methylhydrazine. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007).

引用

页码：5180 / 5182

页数：3

共 43 条

[1] One-pot construction of pyrazoles and isoxazoles with palladium-catalyzed four-component coupling [J].

Ahmed, MSM ;

Kobayashi, K ;

Mori, A .

ORGANIC LETTERS, 2005, 7 (20) :4487-4489

[2] Carbonylative Sonogashira coupling of terminal alkynes with aqueous ammonia [J].

Ahmed, MSM ;

Mori, A .

ORGANIC LETTERS, 2003, 5 (17) :3057-3060

[3] Mechanism of aryl chloride amination: Base-induced oxidative addition [J].

Alcazar-Roman, LM ;

Hartwig, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (51) :12905-12906

[4] Studies on copper(I) catalysed cross-coupling reactions:: A convenient and facile method for the synthesis of diversely substituted α,β-acetylenic ketones [J].

Chowdhury, C ;

Kundu, NG .

TETRAHEDRON, 1999, 55 (22) :7011-7016

[5] Palladium-catalyzed carbonylative coupling of pyridine halides with aryl boronic acids [J].

Couve-Bonnaire, S ;

Carpentier, JF ;

Mortreux, A ;

Castanet, Y .

TETRAHEDRON, 2003, 59 (16) :2793-2799

[6] Direct carbamoylation of aryl halides [J].

Cunico, RF ;

Maity, MC .

ORGANIC LETTERS, 2002, 4 (24) :4357-4359

[7] The first general method for palladium-catalyzed Negishi cross-coupling of aryl and vinyl chlorides:: Use of commercially available Pd(P(t-BU)3)2 as a catalyst [J].

Dai, CY ;

Fu, GC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (12) :2719-2724

[8]

HECK RF, 1995, PALLADIUM REAGENTS O

[9] PREPARATION AND REACTIONS OF TRANS-PD(COPH)(CONR2)(PME3)2 AND TRANS-PDPH(CONR2)(PME3)2 COMPLEXES AS MODELS FOR INTERMEDIATES INVOLVED IN THE PALLADIUM-CATALYZED DOUBLE-CARBONYLATION AND SINGLE-CARBONYLATION REACTIONS OF PHENYL HALIDES [J].

HUANG, L ;

OZAWA, F ;

YAMAMOTO, A .

ORGANOMETALLICS, 1990, 9 (09) :2603-2611

[10] Pd(PhCN)2Cl2/P(t-Bu)3:: A versatile catalyst for sonogashira reactions of aryl bromides at room temperature [J].

Hundertmark, T ;

Littke, AF ;

Buchwald, SL ;

Fu, GC .

ORGANIC LETTERS, 2000, 2 (12) :1729-1731

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