Air-stable CpPd(NHC)Cl (NHC = N-heterocyclic carbene) complexes as highly active precatalysts for Kumada–Tamao–Corriu coupling of aryl and heteroaryl chlorides

Jin, Zhong; Gu, Xiao-Peng; Qiu, Lingling; Wu, Guiping; Song, Huan; Fang, Jianxin

doi:10.1016/j.jorganchem.2010.10.009

Cited by 29 publications

(10 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The Pd complex (η 5 -Cp)(η 1 -Cp)Pd(IPr) ( CpCp Pd ) was synthesized from the reaction of (Cp)Pd(IPr)Cl and sodium cyclopentadienyl in THF (Scheme b). It is unstable in solution at room temperature and decomposes to give the dimeric product (μ-Cp) 2 Pd 2 (IPr) 2 .…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Properties, and Reactivity of Palladium and Nickel NHC Complexes Supported by Combinations of Allyl, Cyclopentadienyl, and Indenyl Ligands

et al. 2013

View full text Add to dashboard Cite

show abstract

Section: Resultsmentioning

confidence: 99%

Synthesis, Properties, and Reactivity of Palladium and Nickel NHC Complexes Supported by Combinations of Allyl, Cyclopentadienyl, and Indenyl Ligands

et al. 2013

View full text Add to dashboard Cite

show abstract

“…6). 60 Of the catalysts screened, [PdCpCl(SIMes)] ( 26) was found to be the optimal catalyst. Interestingly, this is in contrast to general trends found in our work 58 as well as Organ's 52 and Cazin's 59 systems where the bulkier IPr and SIPr were found to be optimal.…”

Section: Kumada-tamao-corriu Cross-couplingmentioning

confidence: 99%

N-Heterocyclic carbene (NHC) ligands and palladium in homogeneous cross-coupling catalysis: a perfect union

2011

View full text Add to dashboard Cite

show abstract

“…In the majority of studies, it is thought that the introduction of bulky ligands in the skeleton of Pd‐NHC complexes is a strong strategy. Also, Pd‐NHC complexes have been proven to be very effective in C−C (such as Suzuki‐Miyaura, Mizoroki‐Heck, Negishi, Sonogashira, Stille, Kumada‐Corriu, Hiyama and Direct arylation reaction) and C‐heteroatom (such as Animation) bond formation reactions.…”

Section: Introductionmentioning

confidence: 99%

2‐Hydroxyethyl‐Substituted Pd‐PEPPSI Complexes: Synthesis, Characterization and the Catalytic Activity in the Suzuki‐Miyaura Reaction for Aryl Chlorides in Aqueous Media

et al. 2018

View full text Add to dashboard Cite

In recent years, PEPPSI (Pyridine‐Enhanced Precatalyst Preparation Stabilization and Initiation) complexes have attracted attention in organometallic chemistry. This study contains the synthesis of the 2‐hydroxyethyl‐substituted Pd‐PEPPSI complexes and their catalytic activity in the Suzuki‐Miyaura reaction aryl chlorides in aqueous media. The Pd‐PEPPSI complexes have been prepared from the 2‐ hydroxyethyl‐substituted N‐heterocyclic carbene (NHC) precursors, palladium chloride and 3‐chloropyridine. The Pd‐PEPPSI complexes have been characterized by using 1H NMR, 13C NMR, FTIR spectroscopy and elemental analysis techniques. The Pd‐PEPPSI complexes have been examined as catalysts in the Suzuki‐Miyaura reactions in aqueous media with arylboronic acid derivatives. Also, they have demonstrated excellent activity in these reactions. Molecular and crystal structure of one of the 2‐hydroxyethyl substituted Pd‐PEPPSI complex was determined by single crystal X‐ray diffraction method. X‐ray studies show that the molecular structure adopts a slightly distorted square‐planar geometry with the palladium (II) center.

show abstract

Air-stable CpPd(NHC)Cl (NHC = N-heterocyclic carbene) complexes as highly active precatalysts for Kumada–Tamao–Corriu coupling of aryl and heteroaryl chlorides

Cited by 29 publications

References 28 publications

Synthesis, Properties, and Reactivity of Palladium and Nickel NHC Complexes Supported by Combinations of Allyl, Cyclopentadienyl, and Indenyl Ligands

Synthesis, Properties, and Reactivity of Palladium and Nickel NHC Complexes Supported by Combinations of Allyl, Cyclopentadienyl, and Indenyl Ligands

N-Heterocyclic carbene (NHC) ligands and palladium in homogeneous cross-coupling catalysis: a perfect union

2‐Hydroxyethyl‐Substituted Pd‐PEPPSI Complexes: Synthesis, Characterization and the Catalytic Activity in the Suzuki‐Miyaura Reaction for Aryl Chlorides in Aqueous Media

Contact Info

Product

Resources

About