Synthesis of 2-ynamides by direct palladium-catalyzed oxidative aminocarbonylation of alk-1-ynes

被引：72

作者：

Gabriele, B ^{[1
]}

Salerno, G

Veltri, L

Costa, M

机构：

[1] Univ Calabria, Dipartimento Chim, I-87030 Rende, Italy

[2] Univ Parma, Dipartimento Chim Organ & Ind, I-43100 Parma, Italy

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2001年 / 622卷 / 1-2期

关键词：

alk-1-ynes; amides; aminocarbonylation; carbonylation; palladium; 2-ynamides;

D O I：

10.1016/S0022-328X(00)00795-6

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A novel synthesis of 2-ynamides (3) by palladium-catalyzed oxidative aminocarbonylation of alk-1-ynes (1) is reported. Reactions are catalyzed by PdI2/KI and are carried out at 100 degreesC in dioxane as the solvent in the presence of dialkylamines (2) as nucleophiles (amine/alk-1-yne molar ratio = 1/1) using a 4/1 CO/air mixture (20 atm total pressure at 25 degreesC). (C) 2001 Elsevier Science B.V. All rights reserved.

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页码：84 / 88

页数：5

相关论文

共 30 条

[1] Nitrogen heterocycles by palladium-catalysed oxidative cyclization-alkoxycarbonylation of acetylenic ureas [J].

Bacchi, A ;

Chiusoli, GP ;

Costa, M ;

Sani, C ;

Gabriele, B ;

Salerno, G .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1998, 562 (01) :35-43

[2] VERSATILE SYNTHESIS OF BETA-LACTAMS, GAMMA-LACTAMS OR OXAZOLINES BY PALLADIUM-CATALYSED OXIDATIVE CARBONYLATION OF 1-SUBSTITUTED PROP-2-YNYLAMINES [J].

BONARDI, A ;

COSTA, M ;

GABRIELE, B ;

SALERNO, G ;

CHIUSOLI, GP .

TETRAHEDRON LETTERS, 1995, 36 (41) :7495-7498

[3] Oxidative carbonylation of phenylacetylene catalyzed by Pd(II) and Cu(I): Experimental tests of forty-one computer-generated mechanistic hypotheses [J].

Bruk, LG ;

Gorodskii, SN ;

Zeigarnik, AV ;

Valdes-Perez, RE ;

Temkin, ON .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1998, 130 (1-2) :29-40

[4] Sequential reaction of carbon dioxide and carbon monoxide with acetylenic amines in the presence of a palladium catalyst [J].

Chiusoli, GP ;

Costa, M ;

Gabriele, B ;

Salerno, G .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1999, 143 (1-3) :297-310

[5] ALKYNES FORM CARBAMOYL PRODUCTS IN THE PRESENCE OF NICKEL(II) SALTS [J].

FANANAS, FJ ;

HOBERG, H .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1984, 277 (01) :135-142

[6] Synthesis of 3,4-bis[(methoxycarbonyl)methyl]thiophene and bis-, ter- and and pentathiophenes with alternating 3,4-bis[(methoxycarbonyl)methyl]-substituted rings [J].

Fazio, A ;

Gabriele, B ;

Salerno, G ;

Destri, S .

TETRAHEDRON, 1999, 55 (02) :485-502

[7]

Fomum Z. T., 1985, J CHEM RES MINIPRINT, V3, P901

[8] An efficient and general synthesis of furan-2-acetic esters by palladium-catalyzed oxidative carbonylation of (Z)-2-en-4-yn-1-ols [J].

Gabriele, B ;

Salerno, G ;

De Pascali, F ;

Costa, M ;

Chiusoli, GP .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (21) :7693-7699

[9] Palladium-catalyzed synthesis of 2E-[(methoxycarbonyl)methylene] tetrahydrofurans:: oxidative cyclization-methoxycarbonylation of 4-yn-1-ols versus cycloisomerization-hydromethoxylation [J].

Gabriele, B ;

Salerno, G ;

De Pascali, F ;

Costa, M ;

Chiusoli, GP .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2000, 593 :409-415

[10] Stereoselective synthesis of (Z)-alpha-(alkoxycarbonyl)methylene beta- and gamma-lactones by palladium-catalysed oxidative carbonylation of alkynols [J].

Gabriele, B ;

Salerno, G ;

DePascali, F ;

Costa, M ;

Chiusoli, GP .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (02) :147-154