Convenient copper- and solvent-free Sonogashira-type alkynylation of aryl iodides and bromides using Pd EnCat™

被引：43

作者：

Carpita, Adriano ^{[2
]}

Ribecai, Arianna ^{[1
]}

机构：

[1] GlaxoSmithKline SpA, Chem Dev Dept, I-37135 Verona, Italy

[2] Univ Pisa, Dipartimento Chim & Chim Ind, I-56126 Pisa, Italy

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 02期

关键词：

Pd EnCat (TM); Sonogashira-type alkynylations; Supported catalysts; Copper-free; Solvent less; Microwave; CROSS-COUPLING REACTIONS; POLYUREA-ENCAPSULATED PALLADIUM; AMINE-FREE; CATALYZED-REACTIONS; TERMINAL ALKYNES; SUZUKI-MIYAURA; EFFICIENT; CHLORIDES; PRECATALYSTS; PLATINUM;

D O I：

10.1016/j.tetlet.2008.10.130

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A straightforward methodology is described for the copper- and solvent-free alkynylations of aryl iodides and bromides using 0.1-0.01 mol% of Pd as Pd EnCat (TM) 40 or TPP30. High yielding reactions can be achieved under aerobic conditions for a variety of activated and deactivated aryl iodides: a few examples with aryl bromides are also described. Microwave irradiation is able to enhance yields and rates of these reactions. (c) 2008 Elsevier Ltd. All rights reserved.

引用

页码：204 / 207

页数：4

共 55 条

[1] General catalysts for the Suzuki-Miyaura and Sonogashira coupling reactions of aryl chlorides and for the coupling of challenging substrate combinations in water
Anderson, KW
Buchwald, SL
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (38) : 6173 - 6177
[2] Palladium nanoparticles as efficient green homogeneous and heterogeneous carbon-carbon coupling precatalysts: A unifying view
Astruc, Didier
[J]. INORGANIC CHEMISTRY, 2007, 46 (06) : 1884 - 1894
[3] Microwave-assisted Suzuki coupling reactions with an encapsulated palladium catalyst for batch and continuous-flow transformations
Baxendale, Ian R.
Griffiths-Jones, Charlotte M.
Ley, Steven V.
Tranmer, Geoffrey K.
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (16) : 4407 - 4416
[4] Poly(aryleneethynylene)s: Syntheses, properties, structures, and applications
Bunz, UHF
[J]. CHEMICAL REVIEWS, 2000, 100 (04) : 1605 - 1644
[5] A copper- and amine-free sonogashira reaction employing aminophosphines as ligands
Cheng, J
Sun, YH
Wang, F
Guo, MJ
Xu, JH
Pan, Y
Zhang, ZG
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (16) : 5428 - 5432
[6] The sonogashira reaction:: A booming methodology in synthetic organic chemistry
Chinchilla, Rafael
Najera, Carmen
[J]. CHEMICAL REVIEWS, 2007, 107 (03) : 874 - 922
[7] A simple and efficient copper-free catalytic system based on a palladacycle for the arylation of alkynes
Consorti, CS
Flores, FR
Rominger, F
Dupont, J
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (1-2) : 133 - 141
[8] A copper-free Sonogashira reaction using a Pd/MgLa mixed oxide
Cwik, A
Hell, Z
Figueras, F
[J]. TETRAHEDRON LETTERS, 2006, 47 (18) : 3023 - 3026
[9] Natural product inspired design of enediyne prodrugs via rearrangement of an allylic double bond
Dai, WM
[J]. CURRENT MEDICINAL CHEMISTRY, 2003, 10 (21) : 2265 - 2283
[10] Palladium-based catalytic systems for the synthesis of conjugated enynes by Sonogashira reactions and related alkynylations
Doucet, Henri
Hierso, Jean-Cyrille
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (06) : 834 - 871

← 1 2 3 4 5 6 →