Homogeneous catalytic aminocarbonylation of iodoalkenes and iodobenzene with amino acid esters under conventional conditions and in ionic liquids

Erno Müller, Gábor Péczely, R. Skoda-Földes, Eszter Takács, George Kokotos, Evagelos Bellis, L. Kollár

Research output: Contribution to journalArticle

58 Citations (Scopus)

Abstract

Amino acid methyl esters were used as amine nucleophiles in palladium catalysed aminocarbonylation of iodobenzene and iodoalkenes (1-iodo-cyclohexene and 17-iodo-androst-16-ene). 2-Oxo-carboxamide type derivatives can be isolated as a result of double CO insertion by using iodobenzene as a substrate at elevated carbon monoxide pressure. On the contrary, carboxamides of expected structure were obtained exclusively in excellent yields in the whole pressure range by using iodoalkenes. The aminocarbonylation of 17-iodo-androst-16-ene in [bmim][PF 6] or [bmim][BF 4] (where bmim=1-butyl-3-methyl- imidazolium cation) ionic liquids was also carried out and the ionic liquid-catalyst mixtures have been reused several times with only a small loss of activity.

Original languageEnglish
Pages (from-to)797-802
Number of pages6
JournalTetrahedron
Volume61
Issue number4
DOIs
Publication statusPublished - Jan 24 2005

Fingerprint

Ionic Liquids
Carbon Monoxide
Esters
Amino Acids
Pressure
Nucleophiles
Palladium
Amines
Cations
Derivatives
Catalysts
Substrates
16-androstene
iodobenzene
cyclohexene

Keywords

  • Amino acid
  • Aminocarbonylation
  • Carbon monoxide
  • Ionic liquid
  • Palladium

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Homogeneous catalytic aminocarbonylation of iodoalkenes and iodobenzene with amino acid esters under conventional conditions and in ionic liquids. / Müller, Erno; Péczely, Gábor; Skoda-Földes, R.; Takács, Eszter; Kokotos, George; Bellis, Evagelos; Kollár, L.

In: Tetrahedron, Vol. 61, No. 4, 24.01.2005, p. 797-802.

Research output: Contribution to journalArticle

Müller, Erno ; Péczely, Gábor ; Skoda-Földes, R. ; Takács, Eszter ; Kokotos, George ; Bellis, Evagelos ; Kollár, L. / Homogeneous catalytic aminocarbonylation of iodoalkenes and iodobenzene with amino acid esters under conventional conditions and in ionic liquids. In: Tetrahedron. 2005 ; Vol. 61, No. 4. pp. 797-802.
@article{cc35267bf4aa4c6596f1393e4792e9d0,
title = "Homogeneous catalytic aminocarbonylation of iodoalkenes and iodobenzene with amino acid esters under conventional conditions and in ionic liquids",
abstract = "Amino acid methyl esters were used as amine nucleophiles in palladium catalysed aminocarbonylation of iodobenzene and iodoalkenes (1-iodo-cyclohexene and 17-iodo-androst-16-ene). 2-Oxo-carboxamide type derivatives can be isolated as a result of double CO insertion by using iodobenzene as a substrate at elevated carbon monoxide pressure. On the contrary, carboxamides of expected structure were obtained exclusively in excellent yields in the whole pressure range by using iodoalkenes. The aminocarbonylation of 17-iodo-androst-16-ene in [bmim][PF 6] or [bmim][BF 4] (where bmim=1-butyl-3-methyl- imidazolium cation) ionic liquids was also carried out and the ionic liquid-catalyst mixtures have been reused several times with only a small loss of activity.",
keywords = "Amino acid, Aminocarbonylation, Carbon monoxide, Ionic liquid, Palladium",
author = "Erno M{\"u}ller and G{\'a}bor P{\'e}czely and R. Skoda-F{\"o}ldes and Eszter Tak{\'a}cs and George Kokotos and Evagelos Bellis and L. Koll{\'a}r",
year = "2005",
month = "1",
day = "24",
doi = "10.1016/j.tet.2004.11.064",
language = "English",
volume = "61",
pages = "797--802",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "4",

}

TY - JOUR

T1 - Homogeneous catalytic aminocarbonylation of iodoalkenes and iodobenzene with amino acid esters under conventional conditions and in ionic liquids

AU - Müller, Erno

AU - Péczely, Gábor

AU - Skoda-Földes, R.

AU - Takács, Eszter

AU - Kokotos, George

AU - Bellis, Evagelos

AU - Kollár, L.

PY - 2005/1/24

Y1 - 2005/1/24

N2 - Amino acid methyl esters were used as amine nucleophiles in palladium catalysed aminocarbonylation of iodobenzene and iodoalkenes (1-iodo-cyclohexene and 17-iodo-androst-16-ene). 2-Oxo-carboxamide type derivatives can be isolated as a result of double CO insertion by using iodobenzene as a substrate at elevated carbon monoxide pressure. On the contrary, carboxamides of expected structure were obtained exclusively in excellent yields in the whole pressure range by using iodoalkenes. The aminocarbonylation of 17-iodo-androst-16-ene in [bmim][PF 6] or [bmim][BF 4] (where bmim=1-butyl-3-methyl- imidazolium cation) ionic liquids was also carried out and the ionic liquid-catalyst mixtures have been reused several times with only a small loss of activity.

AB - Amino acid methyl esters were used as amine nucleophiles in palladium catalysed aminocarbonylation of iodobenzene and iodoalkenes (1-iodo-cyclohexene and 17-iodo-androst-16-ene). 2-Oxo-carboxamide type derivatives can be isolated as a result of double CO insertion by using iodobenzene as a substrate at elevated carbon monoxide pressure. On the contrary, carboxamides of expected structure were obtained exclusively in excellent yields in the whole pressure range by using iodoalkenes. The aminocarbonylation of 17-iodo-androst-16-ene in [bmim][PF 6] or [bmim][BF 4] (where bmim=1-butyl-3-methyl- imidazolium cation) ionic liquids was also carried out and the ionic liquid-catalyst mixtures have been reused several times with only a small loss of activity.

KW - Amino acid

KW - Aminocarbonylation

KW - Carbon monoxide

KW - Ionic liquid

KW - Palladium

UR - http://www.scopus.com/inward/record.url?scp=11044228681&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=11044228681&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2004.11.064

DO - 10.1016/j.tet.2004.11.064

M3 - Article

AN - SCOPUS:11044228681

VL - 61

SP - 797

EP - 802

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 4

ER -