Palladium(0) nanoparticle-catalyzed sp2 C-H activation: a convenient route to alkyl-aryl ketones by direct acylation of aryl bromides and iodides with aldehydes

被引：44

作者：

Adak, Laksmikanta ^{[1
]}

Bhadra, Sukalyan ^{[1
]}

Ranu, Brindaban C. ^{[1
]}

机构：

[1] Indian Assoc Cultivat Sci, Dept Organ Chem, Kolkata 700032, India

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 29期

关键词：

C-H activation; Palladium nanoparticles; Aryl halides; Aldehydes; Alkyl-aryl ketone; COOPERATIVE CATALYSIS; COUPLING REACTION; BOND ACTIVATION; EFFICIENT; HALIDES; ARENES; ACIDS; PD;

D O I：

10.1016/j.tetlet.2010.05.067

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Palladium(0) nanoparticles efficiently catalyze aliphatic aldehyde C H functionalization by aryl halides to produce alkyl aryl ketones in good yields. A wide range of substituted aryl and hetero-aryl bromides/iodides and open-chain aldehydes of varied chain length participated in this reaction. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：3811 / 3814

页数：4

共 41 条

[1] Assisted ruthenium-catalyzed C-H bond activation: Carboxylic acids as cocatalysts for generally applicable direct arylations in apolar solvents [J].

Ackermann, Lutz ;

Vicente, Ruben ;

Althammer, Andreas .

ORGANIC LETTERS, 2008, 10 (11) :2299-2302

[2] Palladium Nanoparticle-Catalyzed C-N Bond Formation. A Highly Regio- and Stereoselective Allylic Amination by Allyl Acetates [J].

Adak, Laksmikanta ;

Chattopadhyay, Kalicharan ;

Ranu, Brindaban C. .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (10) :3982-3985

[3] Nanoparticles as recyclable catalysts: The frontier between homogeneous and heterogeneous catalysis [J].

Astruc, D ;

Lu, F ;

Aranzaes, JR .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (48) :7852-7872

[4] Palladium nanoparticles as efficient green homogeneous and heterogeneous carbon-carbon coupling precatalysts: A unifying view [J].

Astruc, Didier .

INORGANIC CHEMISTRY, 2007, 46 (06) :1884-1894

[5] Oxidative Conversion of α,α-Disubstituted Acetamides to Corresponding One-Carbon-Shorter Ketones Using Hypervalent Iodine (λ5) Reagents in Combination with Tetraethylammonium Bromide [J].

Bellale, Eknath V. ;

Bhalerao, Dinesh S. ;

Akamanchi, Krishnacharya G. .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (23) :9473-9475

[6] Palladium-Nanoparticle-Catalysed Ullmann Reactions in Ionic Liquids with Aldehydes as the Reductants: Scope and Mechanism [J].

Calo, Vincenzo ;

Nacci, Angelo ;

Monopoli, Antonio ;

Cotugno, Pietro .

CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (05) :1272-1279

[7] Insights into directing group ability in palladium-catalyzed C-H bond functionalization [J].

Desai, Lopa V. ;

Stowers, Kara J. ;

Sanford, Melanie S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (40) :13285-13293

[8] Palladium(0) Nanoparticle Catalyzed Cross-Coupling of Allyl Acetates and Aryl and Vinyl Siloxanes [J].

Dey, Raju ;

Chattopadhyay, Kalicharan ;

Ranu, Brinclaban C. .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (23) :9461-9464

[9] An overview of palladium nanocatalysts:: Surface and molecular reactivity [J].

Durand, Jerome ;

Teuma, Emmanuelle ;

Gomez, Montserrat .

EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2008, (23) :3577-3586

[10] Nickel-catalyzed coupling of aryl iodides with aromatic aldehydes: Chemoselective synthesis of ketones [J].

Huang, YC ;

Majumdar, KK ;

Cheng, CH .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (05) :1682-1684

← 1 2 3 4 5 →