Aminocarbonylation of phenylacetylene catalysed by palladium acetate in combination with (2-pyridyl)diphenylphosphine and methanesulfonic acid

被引：40

作者：

Matteoli, U ^{[1
]}

Scrivanti, A ^{[1
]}

Beghetto, V ^{[1
]}

机构：

[1] Univ Venice, Dipartimento Chim, I-30123 Venice, Italy

来源：

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL | 2004年 / 213卷 / 02期

关键词：

alkynes; carbonylation; amides; palladium; aminocarbonylation;

D O I：

10.1016/j.molcata.2003.12.012

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The aminocarbonylation of phenylacetylene has been studied in the presence of the catalytic system formed by palladium acetate in combination with (2-pyridyl)diphenylphosphine and methanesulfonic acid. The catalytic activity is strongly influenced by the nature of the amine: good reaction rates are achieved using amines of low basicity such as aniline. The reaction solvent influences both the activity and the selectivity of the catalyst: the highest reaction rates accompanied by complete regioselectivity towards the branched amide are obtained working in dichloromethane/N-methylpyrrolidinone mixtures. Also the acid to palladium molar ratio and the P(CO) affect to a lower extent the process: the highest catalyst activity is obtained operating at a methanesulfonic acid/Pd molar ratio of 30:1 and at P(CO) = 20 atm. (C) 2004 Elsevier B.V. All rights reserved.

引用

页码：183 / 186

页数：4

共 18 条

[1]

[Anonymous], 1995, CRC HDB CHEM PHYS

[2]

Armarego W.L. F., 1996, PURIFICATION LAB CHE, V4th

[3]

BUCHOLZ FC, 1998, ULLMANS ENCY IND CHE

[4] EFFICIENT PALLADIUM CATALYSTS FOR THE CARBONYLATION OF ALKYNES [J].

DRENT, E ;

ARNOLDY, P ;

BUDZELAAR, PHM .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1993, 455 (1-2) :247-253

[5]

Drent E., 1996, APPL HOMOGENEOUS CAT

[6]

DRENT E, 1992, Patent No. 5128475

[7] Palladium(II) acetate catalyzed efficient synthesis of N-aryl-α,β-unsaturated amides via carbonylative addition of aniline derivatives to aromatic alkynes [J].

El Ali, B ;

Tijani, J ;

El-Ghanam, AM .

APPLIED ORGANOMETALLIC CHEMISTRY, 2002, 16 (07) :369-376

[8] Total regioselective control of the carbonylative coupling of 1-heptyne with aniline and N-methyl aniline catalyzed by palladium(II) and phosphine ligand [J].

El Ali, B ;

Tijani, J ;

El-Ghanam, AM .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2002, 187 (01) :17-33

[9] Palladium(II)-catalyzed regioselective carbonylative coupling of aniline derivatives with terminal aryl acetylenes to give acrylamides under syngas conditions [J].

El Ali, B ;

El-Ghanam, A ;

Fettouhi, M ;

Tijani, J .

TETRAHEDRON LETTERS, 2000, 41 (30) :5761-5764

[10] Esters and N,N-dialkylamides of 2-(trifluoromethyl)acrylic acid (TFMAA) through Pd-catalysed carbonylation of fluorinated unsaturated substrates [J].

Matteoli, U ;

Botteghi, C ;

Sbrogiò, F ;

Beghetto, V ;

Paganelli, S ;

Scrivanti, A .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1999, 143 (1-3) :287-295

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