Benzimidazol-2-ylidene ligated palladacyclic complexes of N,N-dimethylbenzylamine – Synthesis and application to C–C coupling reactions

Green, Kerry‐Ann; Maragh, Paul T.; Abdur‐Rashid, Kamaluddin; Lough, Alan J.; Dasgupta, Tara P.

doi:10.1016/j.ica.2016.04.048

Cited by 8 publications

(4 citation statements)

References 44 publications

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“…Palladium complexes have been used as active catalysts for Suzuki–Miyaura cross‐coupling reactions . However, a limited number of NHC‐bearing palladacycle complexes have been reported as catalysts for this transformation . Thus 3 and 4 were investigated as catalysts for C—C bond forming reactions.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, characterization and catalytic activity in Suzuki–Miyaura coupling of palladacycle complexes with n‐butyl‐substituted N‐heterocyclic carbene ligands

Fırıncı

Günay

Gökçe

2017

Applied Organom Chemis

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A series of monomeric palladacycle complexes bearing n‐butyl‐substituted N‐heterocyclic carbenes, namely [Pd(NHC)X(dmba)] (dmba: dimethylbenzylamine and [Pd(NHC)X(ppy)]; NHC: 1‐n‐butyl‐3‐substituted benzylimidazol‐2‐ylidene; ppy: 2‐phenylpyridine), were prepared either by transmetallation from the corresponding silver carbene complexes or by the reaction of the corresponding acetate‐bridged palladacycle dimer with N‐heterocyclic carbene ligands in high yields. The palladium(II) complexes were characterized using elemental analyses, APCI‐MS, 1H NMR and 13C NMR spectroscopies. These complexes are efficient in the Suzuki–Miyaura coupling reaction between phenylboronic acid and aryl bromides.

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Section: Resultsmentioning

confidence: 99%

Synthesis, characterization and catalytic activity in Suzuki–Miyaura coupling of palladacycle complexes with n‐butyl‐substituted N‐heterocyclic carbene ligands

Fırıncı

Günay

Gökçe

2017

Applied Organom Chemis

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“…The catalytic activity of air stable palladacyclic complexes of N,N-dimethylbenzylamine ligated with bulky(cyclohexyl, adamantyl and t-butyl) benzimidazol-2-ylidene in Suzuki-Miyaura and Heck-Mizoroki coupling reactions of aryl bromides were reported by Dasgupta et al [64] Complex 38 b with greater steric bulkiness that enhances the reductive elimination step in the catalytic cycle showed higher catalytic activity. Both the reactions were performed in presence of 2 mol% of the catalyst, Cs 2 CO 3 base in 1,4 dioxane (Scheme 30).…”

Section: Homogeneous Catalystsmentioning

confidence: 89%

Recent Advances in Benzimidazole Based NHC‐Metal Complex Catalysed Cross‐Coupling Reactions**

Nair

Jayaraj

2022

ChemistrySelect

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In recent years, there has been a substantial increase in the development of efficient, environmentally compatible and cost‐effective catalysts as a replacement for conventional metal catalysts. Among several catalysts developed, metal‐based N‐Heterocyclic carbene (NHC) catalysts have garnered significant attention due to the unique steric and electronic properties imparted by NHCs, making them suitable for a broad spectrum of chemical transformations. Over a decade, benzimidazole based NHCs have been broadly investigated for the synthesis of metal complexes for a variety of catalytic processes. The interesting properties of benzimidazole scaffolds such as the ease of tailoring its electronic and steric properties via simple synthetic modifications, aids in achieving potential catalysts for cross‐coupling reactions and other hydrofunctional transformations. This review focuses on the synthetic approaches developed over recent years (2015–2021) concerning the structural tuning and modulation of the benzimidazole derived NHC ligands to generate catalytically active metal complexes for cross‐coupling reactions such as Heck, Suzuki, Sonogashira, Kumada and dehydrogenative cross‐coupling reactions.

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“…Three palladacycle complexes (152e154) containing N,N-dimethylbenzyl amine (dmba) and the benzimidazol-2-ylidene ligands were prepared [84]: 1,3-di(cyclohexyl) benzimidazol-2-ylidene (BzImCy), 1,3-di(tert-butyl)benzimidazol-2-ylidene (BzImtBu), and 1,3-di(1-adamantyl) benzimidazol-2-ylidene (BzImAd). The catalytic activity of air stable complexes (152e154) (Fig.…”

Section: Mizorokieheck Reactionmentioning

confidence: 99%

Palladium–N-heterocyclic carbene complexes for the Mizoroki–Heck reaction: An appraisal

Balinge¹,

Bhagat²

2017

Comptes Rendus. Chimie

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This article presents a review of the most significant developments with N-heterocyclic carbene (NHC)epalladium catalytic systems used for the Heck reaction. For more than the past two decades, a large number of new NHCePd complexes have been synthesized and characterized. These studies focused on NHCs as a phosphine analogue, but the current review highlights the differences with particular ligands so as to attain a suitable balance between the electronic and bulky environments around the metal. NHCs have gained wide recognition as these ligands act as excellent s-donors that form stable metaleNHCs with strong metalecarbon bonds. For this reason, metaleNHCs are commonly used as they are highly reactive and can selectively serve as catalysts for various chemical transformations. The objective of our article is to highlight significant recent progress in NHCePd(II) complexes and provide an overview of their extensive interaction in the MizorokieHeck reaction.

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Benzimidazol-2-ylidene ligated palladacyclic complexes of N,N-dimethylbenzylamine – Synthesis and application to C–C coupling reactions

Cited by 8 publications

References 44 publications

Synthesis, characterization and catalytic activity in Suzuki–Miyaura coupling of palladacycle complexes with n‐butyl‐substituted N‐heterocyclic carbene ligands

Synthesis, characterization and catalytic activity in Suzuki–Miyaura coupling of palladacycle complexes with n‐butyl‐substituted N‐heterocyclic carbene ligands

Recent Advances in Benzimidazole Based NHC‐Metal Complex Catalysed Cross‐Coupling Reactions**

Palladium–N-heterocyclic carbene complexes for the Mizoroki–Heck reaction: An appraisal

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