Alkoxycarbonylpiperidines as N-nucleophiles in the palladium-catalyzed aminocarbonylation

Attila Takács, Zsuzsanna Kabak-Solt, Gábor Mikle, L. Kollár

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Piperidines possessing ester functionality, such as 2-(methoxycarbonyl) piperidine (methyl pipecolinate), 3-(ethoxycarbonyl)piperidine (ethyl nipecotate), and 4-(ethoxycarbonyl)piperidine (ethyl isonipecotate), were used as N-nucleophiles in palladium-catalyzed aminocarbonylation of iodobenzene and iodoalkenes such as 1-iodocyclohexene and 17-iodoandrost-16-ene. While the aminocarbonylation of both iodoalkenes, carried out under mild reaction conditions, resulted in the exclusive formation of the carboxamide, the same reaction of iodobenzene brought about the mixture of the corresponding carboxamide and 2-ketocarboxamide. The chemoselectivity toward the latter compounds, formed via double carbonyl insertion, was substantially increased by using high carbon monoxide pressure (up to 40 bar). Carboxamides derived from iodoalkenes and ketocarboxamides derived from iodoarene have been obtained in moderate to high yields. Graphical abstract: [Figure not available: see fulltext.]

Original languageEnglish
Pages (from-to)1473-1478
Number of pages6
JournalMonatshefte fur Chemie
Volume145
Issue number9
DOIs
Publication statusPublished - 2014

Fingerprint

Nucleophiles
Palladium
Piperidines
Carbon Monoxide
Esters
piperidine
iodobenzene

Keywords

  • Amines
  • Amino acids
  • Carbonylations
  • Carboxylic acids
  • Heterocycles
  • Steroids

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Alkoxycarbonylpiperidines as N-nucleophiles in the palladium-catalyzed aminocarbonylation. / Takács, Attila; Kabak-Solt, Zsuzsanna; Mikle, Gábor; Kollár, L.

In: Monatshefte fur Chemie, Vol. 145, No. 9, 2014, p. 1473-1478.

Research output: Contribution to journalArticle

Takács, Attila ; Kabak-Solt, Zsuzsanna ; Mikle, Gábor ; Kollár, L. / Alkoxycarbonylpiperidines as N-nucleophiles in the palladium-catalyzed aminocarbonylation. In: Monatshefte fur Chemie. 2014 ; Vol. 145, No. 9. pp. 1473-1478.
@article{56c1754a43c54b749e37d1b5f669f173,
title = "Alkoxycarbonylpiperidines as N-nucleophiles in the palladium-catalyzed aminocarbonylation",
abstract = "Piperidines possessing ester functionality, such as 2-(methoxycarbonyl) piperidine (methyl pipecolinate), 3-(ethoxycarbonyl)piperidine (ethyl nipecotate), and 4-(ethoxycarbonyl)piperidine (ethyl isonipecotate), were used as N-nucleophiles in palladium-catalyzed aminocarbonylation of iodobenzene and iodoalkenes such as 1-iodocyclohexene and 17-iodoandrost-16-ene. While the aminocarbonylation of both iodoalkenes, carried out under mild reaction conditions, resulted in the exclusive formation of the carboxamide, the same reaction of iodobenzene brought about the mixture of the corresponding carboxamide and 2-ketocarboxamide. The chemoselectivity toward the latter compounds, formed via double carbonyl insertion, was substantially increased by using high carbon monoxide pressure (up to 40 bar). Carboxamides derived from iodoalkenes and ketocarboxamides derived from iodoarene have been obtained in moderate to high yields. Graphical abstract: [Figure not available: see fulltext.]",
keywords = "Amines, Amino acids, Carbonylations, Carboxylic acids, Heterocycles, Steroids",
author = "Attila Tak{\'a}cs and Zsuzsanna Kabak-Solt and G{\'a}bor Mikle and L. Koll{\'a}r",
year = "2014",
doi = "10.1007/s00706-014-1254-1",
language = "English",
volume = "145",
pages = "1473--1478",
journal = "Monatshefte fur Chemie",
issn = "0026-9247",
publisher = "Springer Wien",
number = "9",

}

TY - JOUR

T1 - Alkoxycarbonylpiperidines as N-nucleophiles in the palladium-catalyzed aminocarbonylation

AU - Takács, Attila

AU - Kabak-Solt, Zsuzsanna

AU - Mikle, Gábor

AU - Kollár, L.

PY - 2014

Y1 - 2014

N2 - Piperidines possessing ester functionality, such as 2-(methoxycarbonyl) piperidine (methyl pipecolinate), 3-(ethoxycarbonyl)piperidine (ethyl nipecotate), and 4-(ethoxycarbonyl)piperidine (ethyl isonipecotate), were used as N-nucleophiles in palladium-catalyzed aminocarbonylation of iodobenzene and iodoalkenes such as 1-iodocyclohexene and 17-iodoandrost-16-ene. While the aminocarbonylation of both iodoalkenes, carried out under mild reaction conditions, resulted in the exclusive formation of the carboxamide, the same reaction of iodobenzene brought about the mixture of the corresponding carboxamide and 2-ketocarboxamide. The chemoselectivity toward the latter compounds, formed via double carbonyl insertion, was substantially increased by using high carbon monoxide pressure (up to 40 bar). Carboxamides derived from iodoalkenes and ketocarboxamides derived from iodoarene have been obtained in moderate to high yields. Graphical abstract: [Figure not available: see fulltext.]

AB - Piperidines possessing ester functionality, such as 2-(methoxycarbonyl) piperidine (methyl pipecolinate), 3-(ethoxycarbonyl)piperidine (ethyl nipecotate), and 4-(ethoxycarbonyl)piperidine (ethyl isonipecotate), were used as N-nucleophiles in palladium-catalyzed aminocarbonylation of iodobenzene and iodoalkenes such as 1-iodocyclohexene and 17-iodoandrost-16-ene. While the aminocarbonylation of both iodoalkenes, carried out under mild reaction conditions, resulted in the exclusive formation of the carboxamide, the same reaction of iodobenzene brought about the mixture of the corresponding carboxamide and 2-ketocarboxamide. The chemoselectivity toward the latter compounds, formed via double carbonyl insertion, was substantially increased by using high carbon monoxide pressure (up to 40 bar). Carboxamides derived from iodoalkenes and ketocarboxamides derived from iodoarene have been obtained in moderate to high yields. Graphical abstract: [Figure not available: see fulltext.]

KW - Amines

KW - Amino acids

KW - Carbonylations

KW - Carboxylic acids

KW - Heterocycles

KW - Steroids

UR - http://www.scopus.com/inward/record.url?scp=84906064050&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84906064050&partnerID=8YFLogxK

U2 - 10.1007/s00706-014-1254-1

DO - 10.1007/s00706-014-1254-1

M3 - Article

VL - 145

SP - 1473

EP - 1478

JO - Monatshefte fur Chemie

JF - Monatshefte fur Chemie

SN - 0026-9247

IS - 9

ER -