A cyclobutene-1,2-bis(imidazolium) salt as preligand for palladium-catalyzed cross-coupling reactions: Properties and applications

Alireza Rahimi, I. Pápai, Údám Madarász, Mimoza Gjikaj, Jan C. Namyslo, Andreas Schmidt

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Spectroscopic investigations and the results of calculations on the title bis-imidazolium salt, its mono-and bis-carbenes, and its interactions with palladium are presented. In addition, we report on the scope and limitations of metal-catalyzed cross-coupling reactions performed with the title bis-imidazolium salt. The salt proved to be an efficient ligand precursor in room-temperature Suzuki-Miyaura reactions, C-C couplings with sterically extremely hindered biaryls,selective thiophene arylations, and couplings with vinylic chlorides. Spectroscopic investigations and the results of calculations on the title bis-imidazolium salt, its mono-and bis-carbenes, and its interactions with palladium are presented. In addition, we report on the scope and limitations of metal-catalyzed cross-coupling reactions performed with the title bis-imidazolium salt.

Original languageEnglish
Pages (from-to)754-763
Number of pages10
JournalEuropean Journal of Organic Chemistry
Issue number4
DOIs
Publication statusPublished - 2012

Fingerprint

cross coupling
Cross Reactions
Palladium
palladium
Salts
salts
carbenes
Metals
Thiophenes
thiophenes
metals
Chlorides
chlorides
interactions
Ligands
ligands
Temperature
room temperature
carbene

Keywords

  • Arylation
  • Carbenes
  • Cross-coupling
  • Nitrogen heterocycles
  • Palladium

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry

Cite this

A cyclobutene-1,2-bis(imidazolium) salt as preligand for palladium-catalyzed cross-coupling reactions : Properties and applications. / Rahimi, Alireza; Pápai, I.; Madarász, Údám; Gjikaj, Mimoza; Namyslo, Jan C.; Schmidt, Andreas.

In: European Journal of Organic Chemistry, No. 4, 2012, p. 754-763.

Research output: Contribution to journalArticle

Rahimi, Alireza ; Pápai, I. ; Madarász, Údám ; Gjikaj, Mimoza ; Namyslo, Jan C. ; Schmidt, Andreas. / A cyclobutene-1,2-bis(imidazolium) salt as preligand for palladium-catalyzed cross-coupling reactions : Properties and applications. In: European Journal of Organic Chemistry. 2012 ; No. 4. pp. 754-763.
@article{62ef86f05e61490ba1c58f80d48fdb79,
title = "A cyclobutene-1,2-bis(imidazolium) salt as preligand for palladium-catalyzed cross-coupling reactions: Properties and applications",
abstract = "Spectroscopic investigations and the results of calculations on the title bis-imidazolium salt, its mono-and bis-carbenes, and its interactions with palladium are presented. In addition, we report on the scope and limitations of metal-catalyzed cross-coupling reactions performed with the title bis-imidazolium salt. The salt proved to be an efficient ligand precursor in room-temperature Suzuki-Miyaura reactions, C-C couplings with sterically extremely hindered biaryls,selective thiophene arylations, and couplings with vinylic chlorides. Spectroscopic investigations and the results of calculations on the title bis-imidazolium salt, its mono-and bis-carbenes, and its interactions with palladium are presented. In addition, we report on the scope and limitations of metal-catalyzed cross-coupling reactions performed with the title bis-imidazolium salt.",
keywords = "Arylation, Carbenes, Cross-coupling, Nitrogen heterocycles, Palladium",
author = "Alireza Rahimi and I. P{\'a}pai and {\'U}d{\'a}m Madar{\'a}sz and Mimoza Gjikaj and Namyslo, {Jan C.} and Andreas Schmidt",
year = "2012",
doi = "10.1002/ejoc.201101378",
language = "English",
pages = "754--763",
journal = "LIEBIGS ANN. CHEM.",
issn = "1434-193X",
publisher = "Wiley-VCH Verlag",
number = "4",

}

TY - JOUR

T1 - A cyclobutene-1,2-bis(imidazolium) salt as preligand for palladium-catalyzed cross-coupling reactions

T2 - Properties and applications

AU - Rahimi, Alireza

AU - Pápai, I.

AU - Madarász, Údám

AU - Gjikaj, Mimoza

AU - Namyslo, Jan C.

AU - Schmidt, Andreas

PY - 2012

Y1 - 2012

N2 - Spectroscopic investigations and the results of calculations on the title bis-imidazolium salt, its mono-and bis-carbenes, and its interactions with palladium are presented. In addition, we report on the scope and limitations of metal-catalyzed cross-coupling reactions performed with the title bis-imidazolium salt. The salt proved to be an efficient ligand precursor in room-temperature Suzuki-Miyaura reactions, C-C couplings with sterically extremely hindered biaryls,selective thiophene arylations, and couplings with vinylic chlorides. Spectroscopic investigations and the results of calculations on the title bis-imidazolium salt, its mono-and bis-carbenes, and its interactions with palladium are presented. In addition, we report on the scope and limitations of metal-catalyzed cross-coupling reactions performed with the title bis-imidazolium salt.

AB - Spectroscopic investigations and the results of calculations on the title bis-imidazolium salt, its mono-and bis-carbenes, and its interactions with palladium are presented. In addition, we report on the scope and limitations of metal-catalyzed cross-coupling reactions performed with the title bis-imidazolium salt. The salt proved to be an efficient ligand precursor in room-temperature Suzuki-Miyaura reactions, C-C couplings with sterically extremely hindered biaryls,selective thiophene arylations, and couplings with vinylic chlorides. Spectroscopic investigations and the results of calculations on the title bis-imidazolium salt, its mono-and bis-carbenes, and its interactions with palladium are presented. In addition, we report on the scope and limitations of metal-catalyzed cross-coupling reactions performed with the title bis-imidazolium salt.

KW - Arylation

KW - Carbenes

KW - Cross-coupling

KW - Nitrogen heterocycles

KW - Palladium

UR - http://www.scopus.com/inward/record.url?scp=84856159567&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84856159567&partnerID=8YFLogxK

U2 - 10.1002/ejoc.201101378

DO - 10.1002/ejoc.201101378

M3 - Article

AN - SCOPUS:84856159567

SP - 754

EP - 763

JO - LIEBIGS ANN. CHEM.

JF - LIEBIGS ANN. CHEM.

SN - 1434-193X

IS - 4

ER -