Mono and Dinuclear Palladium Pincer Complexes of NNSe Ligand as a Catalyst for Decarboxylative Direct C−H Heteroarylation of (Hetero)arenes

Singh, Sohan; Shinde, Vikki N.; Kumar, Sunil; Meena, Neha; Bhuvanesh, Nattamai; Rangan, Krishnan; Kumar, Anil; Joshi, Hemant

doi:10.1002/asia.202300628

Cited by 4 publications

(3 citation statements)

References 140 publications

(33 reference statements)

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“…further validates the coordination of ligands with palladium precursor (Figure 1). [15] Additionally, the HRMS data of C1 showed a peak at m/z 891.2028 which was correlated to [M + H] + ion (Figure s5 in SI).…”

Section: Resultsmentioning

confidence: 95%

Macrocyclic Sulfur Ligand Stabilized Trans‐Palladium Dichloride Complex: Syntheses, Structure, Chlorine Rotation, and Application in α‐Olefination of Nitriles by Primary Alcohols

Kumar,

Sharma,

Mahala

et al. 2024

Chemistry An Asian Journal

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Herein, we have reported synthesis of a macrocyclic organosulfur ligand (L1) having seventeen‐membered macrocyclic ring. Subsequently, the corresponding trans‐palladium complex (C1) of bulky macrocyclic organosulfur ligand was synthesized by reacting it with PdCl2(CH3CN)2 salt. The newly synthesized ligand and complex were characterized using various analytical and spectroscopic techniques such as 1H, 13C{1H} Nuclear Magnetic Resonance (NMR), Ultraviolet–visible (UV‐Visible), Fourier Transform Infrared (FTIR) Spectroscopy, High‐Resolution Mass Spectrometry (HRMS), and elemental analysis. The binding mode of macrocyclic sulfur ligand with palladium was studied using single crystal X‐ray diffraction technique. The complex showed a square planar geometry with trans orientation of two ligands around the palladium center. The potential energy surface (PES) for the rotational process of C1 suggested a barrier of ~23.81 kcal/mol for chlorine rotation. Furthermore, the palladium complex (C1) was used as a catalyst(2.5 mol %) for α‐olefination of nitriles by primary alcohols. The α,β‐unsaturated nitrile compounds were found to be the major product of reaction (57‐78% yield) with broad substrate scope and large functional group tolerance. Notably, the saturated nitrile product was not observed during the reaction. The mechanistic studies suggested formation of H2 and H2O as only by‐products of the reaction thereby making the protocol greener and sustainable.

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Section: Resultsmentioning

confidence: 95%

Macrocyclic Sulfur Ligand Stabilized Trans‐Palladium Dichloride Complex: Syntheses, Structure, Chlorine Rotation, and Application in α‐Olefination of Nitriles by Primary Alcohols

Kumar,

Sharma,

Mahala

et al. 2024

Chemistry An Asian Journal

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“…reported a palladium complex with a selenium analogue ligand where Pd–Se Ph (2.3651 Å) bond length is larger than that of Pd–S Ph bond lengths found in complexes C1 , C3 , and C4 due to the larger size of selenium. 36…”

Section: Resultsmentioning

confidence: 99%

Pd(ii) complexes bearing NNS pincer ligands: unveiling potent cytotoxicity against breast and pancreatic cancer

Tanwar,

Kaur,

Sudheendranath

et al. 2024

Dalton Trans.

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“…Expanding on this approach, Singh et al developed dinuclear palladium pincer complexes incorporating a Pd-Pd bond based on N,N,Se-ligands [44]. Bipyridine compounds can be synthesized in good yield by combining the decarboxylation of picolinic acid and the C-H activation of pyridine using this complex as a catalyst (Figure 4b).…”

Section: Other Cross-coupling Reactions In Homogeneous Catalytic Systemsmentioning

confidence: 99%

Recent Progress on the Synthesis of Bipyridine Derivatives

Yamanoi

2024

Molecules

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Bipyridine and related compounds are starting materials or precursors for a variety of valuable substances such as biologically active molecules, ligands for catalysts, photosensitizers, viologens, and supramolecular architectures. Thus, it is important to classify their synthesis methods and understand their characteristics. Representative examples include methods using homo and heterocoupling of pyridine derivatives in the presence of a catalyst. Because bipyridine compounds strongly coordinate with metal centers, a decrease in catalytic activity and yield is often observed in the reaction system. To address this issue, this review provides insights into advances over the last ~30 years in bipyridine synthesis using metal complexes under both homogeneous and heterogeneous conditions. Moreover, strategies for bipyridine synthesis involving sulfur and phosphorous compounds are examined. These alternative pathways offer promising avenues for overcoming the challenges associated with traditional catalysis methods, providing a more comprehensive understanding of the synthesis landscape.

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Mono and Dinuclear Palladium Pincer Complexes of NNSe Ligand as a Catalyst for Decarboxylative Direct C−H Heteroarylation of (Hetero)arenes

Cited by 4 publications

References 140 publications

Macrocyclic Sulfur Ligand Stabilized Trans‐Palladium Dichloride Complex: Syntheses, Structure, Chlorine Rotation, and Application in α‐Olefination of Nitriles by Primary Alcohols

Macrocyclic Sulfur Ligand Stabilized Trans‐Palladium Dichloride Complex: Syntheses, Structure, Chlorine Rotation, and Application in α‐Olefination of Nitriles by Primary Alcohols

Pd(ii) complexes bearing NNS pincer ligands: unveiling potent cytotoxicity against breast and pancreatic cancer

Recent Progress on the Synthesis of Bipyridine Derivatives

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