Towards phosphine-free Pd(II) pincer complexes for catalyzing Suzuki-Miyaura cross-coupling reaction in aqueous medium

Peter, Jerome; Sathishkumar, Pushpanathan N.; Bhuvanesh, Nattamai; Karvembu, Ramasamy

doi:10.1016/j.jorganchem.2017.03.045

Cited by 20 publications

(28 citation statements)

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“…Though many chemists have studied the effect of different pincer ligands on the catalytic activity of their complexes, only little attention has been paid to understand the role of ancillary ligand in pincer complexes. Our focus towards this direction has already achieved phosphine‐free Pd(II)‐NNN pincer catalysts for the SMC reaction, where we have found that CH 3 CN can replace PPh 3 ancillary ligand without compromising the activity . Subsequently we have compared the catalytic activity between the pincer complexes containing CH 3 CN ( sp hybridized N) ancillary ligand and those with bulky 2‐bromopyridine ( sp 2 hybridized N), towards the same SMC reaction; the results are being presented in this paper.…”

Section: Introductionmentioning

confidence: 53%

“…Precursor complexes ( 1’ ‐ 4’ ) have been synthesized according to a previously reported protocol . Catalysts ( 1‐4 ) are obtained directly from the reaction between [Pd(L)(CH 3 CN)] ( 1’ ‐ 4’ ) and 2‐bromopyridine (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

“…The 1 H‐NMR spectra of the catalysts were recorded in CDCl 3 , which showed two new doublets for the methylene protons. The chemical shift of the methyl protons of CH 3 CN (2.05‐2.01 ppm) disappeared in the spectra of the catalysts . In the 13 C NMR spectra of 1–4 , there was a mild up field shift of the peaks of carbonyl carbons.…”

Section: Resultsmentioning

confidence: 99%

“…The crystal structure shows distorted square planar geometry around Pd(II) ion (Figure ). 2‐Bromopyridine in 1 was situated slightly away from the Pd(II) ion (Pd‐N, 2.047 Å) compared to CH 3 CN in 1’ (Pd‐N, 2.011 Å) . The bond length between Pd(II) and the anionic N atoms was found to be in the range of 2.027‐2.033 Å.…”

Section: Resultsmentioning

confidence: 99%

“…Numerous ONO, NNN, PCP, PNP and NCN pincer complexes have been reported, which act effectively as catalysts for the coupling reactions, C‐H activation, water splitting, asymmetric transformations, etc . Designing such pincer ligands has drawn enormous attention in the past few years .…”

Section: Introductionmentioning

confidence: 99%

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Effect of 2‐Bromopyridine Ancillary Ligand in the Catalysis of Pd(II)‐NNN Pincer Complexes towards Suzuki‐Miyaura Cross‐Coupling Reaction

et al. 2019

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Pd(II)‐NNN pincer complexes containing sterically hindered 2‐bromopyridine (sp2 hybridized N donor) as ancillary ligand have been synthesized in order to compare their catalytic efficiency with the reported analogous complexes containing acetonitrile (sp hybridized N donor) ancillary ligand. The complexes have been characterized by analytical and spectroscopic techniques. Single crystal XRD reveals distorted square planar structure of complex 1. These complexes have been investigated as catalysts for the Suzuki‐Miyaura cross‐coupling (SMC) reaction. The scope is extended using various substituted aromatic/aliphatic halides. The activity of the Pd(II)‐NNN pincer complexes bearing bulky 2‐bromopyridine ancillary ligand is not higher compared to that of the complexes with acetonitrile ancillary ligand, which shows superiority of acetonitrile ancillary ligand.

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Section: Introductionmentioning

confidence: 53%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Effect of 2‐Bromopyridine Ancillary Ligand in the Catalysis of Pd(II)‐NNN Pincer Complexes towards Suzuki‐Miyaura Cross‐Coupling Reaction

et al. 2019

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Catalytic Assessment of Copper(I) Complexes and a Polymer Analog towards the One‐Pot Synthesis of Imines and Quinoxalines

et al. 2019

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Three copper(I) complexes, [CuCl(L)(PPh 3 ) 2 ] [L = FL (1), BL (2) or TL (3)] were prepared from [(PPh 3 ) 2 Cu-(μ-Cl) 2 Cu(PPh 3 )] and N-carbamothioylfuran-2-carboxamide (FL), N-carbamothioylbenzamide (BL) or N-carbamothioylthiophene-2-carboxamide (TL) ligands in benzene and four-coordinated tetrahedral copper complexes were well characterized by various spectroscopic techniques (UV/Vis, FT-IR, 1 H NMR, 13 C NMR and 31 P NMR). The molecular structure of the ligands (FL and BL) and complexes was established from single-crystal X-ray diffraction studies. Copper complexes have been shown to cata- [a]

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Importance of some factors on the Suzuki‐Miyaura cross‐coupling reaction

Akkoç

2021

J Chinese Chemical Soc

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This review was designed to give an overview of the significant parameters in Suzuki‐Miyaura coupling (SMC) reactions, which are a powerful tool for the formation of the carbon–carbon (CC) bond. Since the SMC reaction depends on factors such as solvent, base, temperature, time, catalyst amount, substituent in aryl halides, and molar ratios of the substrates, all these parameters should be screened for a successful SMC reaction. After finding the optimum reaction conditions, the SMC reaction's products of boronic acid derivatives with aryl halides can be obtained in high yields.

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Towards phosphine-free Pd(II) pincer complexes for catalyzing Suzuki-Miyaura cross-coupling reaction in aqueous medium

Cited by 20 publications

References 62 publications

Effect of 2‐Bromopyridine Ancillary Ligand in the Catalysis of Pd(II)‐NNN Pincer Complexes towards Suzuki‐Miyaura Cross‐Coupling Reaction

Effect of 2‐Bromopyridine Ancillary Ligand in the Catalysis of Pd(II)‐NNN Pincer Complexes towards Suzuki‐Miyaura Cross‐Coupling Reaction

Catalytic Assessment of Copper(I) Complexes and a Polymer Analog towards the One‐Pot Synthesis of Imines and Quinoxalines

Importance of some factors on the Suzuki‐Miyaura cross‐coupling reaction

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