Mechanistic Insights into the One-Pot Synthesis of Propargylamines from Terminal Alkynes and Amines in Chlorinated Solvents Catalyzed by Gold Compounds and Nanoparticles

被引：65

作者：

Aguilar, David ^{[3
]}

Contel, Maria ^{[1
,2
]}

Urriolabeitia, Esteban P. ^{[3
]}

机构：

[1] CUNY, Brooklyn Coll, Dept Chem, Brooklyn, NY 11210 USA

[2] CUNY, Grad Ctr, Brooklyn, NY 11210 USA

[3] Univ Zaragoza, CSIC, Inst Ciencia Mat Aragon, Dept Compuestos Organometal, E-50009 Zaragoza, Spain

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2010年 / 16卷 / 30期

关键词：

alkynes; C-C coupling; C-Cl activation; catalysis; gold; 3-COMPONENT COUPLING REACTION; DICHLOROMETHANE ACTIVATION; IMINOPHOSPHORANE COMPLEXES; BOND ACTIVATION; DIRECT-ADDITION; ALDEHYDE; COPPER; SILVER; 2,3,4,5-TETRAHYDROPYRIDINES; 5-ALKYNYLAMINES;

D O I：

10.1002/chem.201000587

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Propargylamines can be obtained from secondary amines and terminal alkynes in chlorinated solvents by a three- and two-component synthesis catalyzed by gold compounds and nanoparticles (Au-NP) under mild conditions. The use of dichloromethane allows for the activation of two C-Cl bonds and a clean transfer of the methylene fragment to the final product. The scope of the reaction as well as the influence of different gold(III) cycloaurated complexes and salts has been investigated. The involvement of gold nanoparticles generated in situ in the process is discussed and a plausible reaction mechanism is proposed on the basis of the data obtained.

引用

页码：9287 / 9296

页数：10

共 78 条

[1] Organogold(III) iminophosphorane complexes as efficient catalysts in the addition of 2-methylfuran and electron-rich arenes to methyl vinyl ketone [J].

Aguilar, David ;

Contel, Maria ;

Navarro, Rafael ;

Urriolabeitia, Esteban P. .

ORGANOMETALLICS, 2007, 26 (18) :4604-4611

[2] Gold(III) iminophosphorane complexes as catalysts in C-C and C-O bond formations [J].

Aguilar, David ;

Contel, Maria ;

Navarro, Rafael ;

Soler, Tatiana ;

Urriolabeitia, Esteban P. .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2009, 694 (04) :486-493

[3] Alternative synthetic methods through new developments in catalysis by gold [J].

Arcadi, Antonio .

CHEMICAL REVIEWS, 2008, 108 (08) :3266-3325

[4] Novel one-step synthesis of amine-stabilized aqueous colloidal gold nanoparticles [J].

Aslam, M ;

Fu, L ;

Su, M ;

Vijayamohanan, K ;

Dravid, VP .

JOURNAL OF MATERIALS CHEMISTRY, 2004, 14 (12) :1795-1797

[5] Productive chloroarene C-Cl bond activation: Palladium/phosphine-catalyzed methods for oxidation of alcohols and hydrodechlorination of chloroarenes [J].

Bei, XH ;

Hagemeyer, A ;

Volpe, A ;

Saxton, R ;

Turner, H ;

Guram, AS .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (25) :8626-8633

[6] Mild and efficient synthesis of propargylamines by copper-catalyzed Mannich reaction [J].

Bieber, LW ;

da Silva, MF .

TETRAHEDRON LETTERS, 2004, 45 (45) :8281-8283

[7] SYNTHESIS OF BIS(PHOSPHA-LAMDA-5-AZENES) BY A REDOX-CONDENSATION REACTION - FORMATION OF AN ANOMALOUS N-CYANOPHOSPHA-LAMDA-5-AZENE FROM UREA [J].

BITTNER, S ;

POMERANTZ, M ;

ASSAF, Y ;

KRIEF, P ;

XI, SK ;

WITCZAK, MK .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (01) :1-5

[8]

Brunet JJ, 1998, EUR J INORG CHEM, P349

[9] SYNTHESIS OF THIOL-DERIVATIZED GOLD NANOPARTICLES IN A 2-PHASE LIQUID-LIQUID SYSTEM [J].

BRUST, M ;

WALKER, M ;

BETHELL, D ;

SCHIFFRIN, DJ ;

WHYMAN, R .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (07) :801-802

[10] Hydroxyapatite supported copper catalyst for effective three-component coupling [J].

Choudary, BM ;

Sridhar, C ;

Kantam, ML ;

Sreedhar, B .

TETRAHEDRON LETTERS, 2004, 45 (39) :7319-7321

← 1 2 3 4 5 6 7 8 →