Rational Design of Sterically Hindered and Unsymmetrical NpyNimOph Pincer‐Type Ligands and Their Palladium(II) Complexes: Catalytic Applications in Suzuki–Miyaura Reaction and Allylation of Aldehydes

Maji, Ankur; Singh, Ovender; Rathi, Sweety; Ghosh, Kaushik

doi:10.1002/slct.201900946

Cited by 11 publications

(1 citation statement)

References 77 publications

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“…Bourland et al reported a chiral tridentate ligand for vanadium metal salts; the catalysts were used in asymmetric selenide oxidation with in situ [2, 3] sigmatropic rearrangement . Although extensive research has been conducted on palladium complexes with [NNO]-, − [ONO]-, − and [CNO]-type − tridentate ligands, there are only limited examples of palladium complexes possessing chiral tridentate ligands. , Therefore, we envisioned that the synthesis and application of such complexes would be a valuable research topic. Although extensive research has been conducted on palladium complexes with [NNO]-, − [ONO]-, − and [CNO]-type − tridentate ligands, there are only limited examples of palladium complexes possessing chiral tridentate ligands − More importantly, to the best of our knowledge, there is no report on palladium complexes possessing chiral [ONO]-type tridentate ligands …”

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Selective Formation of Mononuclear Palladium and Acetonitrile-Bridged Dinuclear Palladium Complexes Containing a Chiral Tridentate Ligand

et al. 2021

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From the chiral Schiff base tridentate ligand L Ph , unusual acetonitrile-bridged dinuclear palladium complex 1 and organopalladium complex 1′ were synthesized selectively by using acetonitrile and ethanol, respectively. The chiral tridentate Schiff base ligand was bound to the palladium metal center with different chelation modes ([ONO] for 1 and [CNO] for 1′). Complex 1 constitutes the first example of dinuclear metal complexes connected only by a bridging acetonitrile, in which an exceptionally short CN bond distance [0.945( 12) Å] of bridged acetonitrile was observed. To study the influence of a phenyl group attached to an imine, the phenyl-free ligand L H was prepared and used. In that case, an acetonitrile bridge was not observed. Theoretical calculation studies supporting the formation of 1 and 1′ are favored. * sı Supporting InformationThe Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.inorgchem.1c03391.Experimental procedures, analytical data of the complexes with 1 H NMR, IR, and MS spectra of 1, 1′, and 2, X-ray crystallographic data for 1, 1′, and 2, and density functional theory calculations (PDF)Accession Codes CCDC 2043775, 2043777, and 2095625 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk

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Selective Formation of Mononuclear Palladium and Acetonitrile-Bridged Dinuclear Palladium Complexes Containing a Chiral Tridentate Ligand

et al. 2021

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Well Defined Phosphine Free Ni‐Catalyzed Dehydrogenation of Secondary Alcohols for the Synthesis of Ketones and Ketazines

Maji,

Singh,

Sharma

et al. 2024

Chemistry An Asian Journal

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In this work, we unveil a novel synthesis of bench stable Ni (II) complexes supported by tetradentate Schiff‐base ligands and the complexes were devoid of any phosphine or phosphine‐based ligand. These Ni‐complexes were successfully applied for the dehydrogenation of secondary alcohols for ketone and ketazine syntheses. Secondary alcohols with different functional groups were well tolerated during catalytic cycle. Moreover, we successfully extended this protocol for the synthesis of biologically significant ketones and ketazines. On the basis of various control experiments, probable reaction pathway was proposed and an acceptorless alcohol dehydrogenation mechanism was suggested.

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Efficient Organoruthenium Catalysts for α‐Alkylation of Ketones and Amide with Alcohols: Synthesis of Quinolines via Hydrogen Borrowing Strategy and their Mechanistic Studies

Maji

Singh

et al. 2020

ChemCatChem

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A new family of phosphine free organometallic ruthenium(II) catalysts (Ru1–Ru4) supported by bidentate NN Schiff base ligands (L1–L4 where L1=N,N‐dimethyl‐4‐((2‐phenyl‐2‐(pyridin‐2‐ylmethyl)hydrazineylidene)methyl) aniline, L2=N,N‐diethyl‐4‐((2‐phenyl‐2‐(pyridin‐2‐ylmethyl)hydrazineylidene)methyl)aniline, L3=N,N‐dimethyl‐4‐((2‐phenyl‐2‐(pyridin‐2‐yl)hydrazineylidene)methyl)‐ aniline and L4=N,N‐diethyl‐4‐((2‐phenyl‐2‐(pyridin‐2‐yl)hydrazineylidene)methyl) aniline) was prepared and characterized. These half‐sandwich complexes acted as catalysts for C−C bond formation and exhibited excellent performance in the dehydrogenative coupling of ketones and amides. In the synthesis of C–C bonds, alcohols were utilized as the alkylating agent. A broad range of substrates, including sterically hindered ketones and alcohols, were well tolerated under the optimized conditions (TON up to 47000 and TOF up to 11750 h−1). This ruthenium (II) catalysts were also active towards the dehydrogenative cyclization of o‐amino benzyl alcohol for the formation of quinolines derivatives. Various polysubstituted quinolines were synthesized in moderate to excellent yields (TON up to 71000 and TOF up to 11830 h−1). Control experiments were carried out and the ruthenium hydride intermediate was characterized to support the reaction mechanism and a probable reaction pathway of dehydrogenative coupling for the C−C bond formation has been proposed.

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Rational Design of Sterically Hindered and Unsymmetrical N_pyN_imO_ph Pincer‐Type Ligands and Their Palladium(II) Complexes: Catalytic Applications in Suzuki–Miyaura Reaction and Allylation of Aldehydes

Cited by 11 publications

References 77 publications

Selective Formation of Mononuclear Palladium and Acetonitrile-Bridged Dinuclear Palladium Complexes Containing a Chiral Tridentate Ligand

Selective Formation of Mononuclear Palladium and Acetonitrile-Bridged Dinuclear Palladium Complexes Containing a Chiral Tridentate Ligand

Well Defined Phosphine Free Ni‐Catalyzed Dehydrogenation of Secondary Alcohols for the Synthesis of Ketones and Ketazines

Efficient Organoruthenium Catalysts for α‐Alkylation of Ketones and Amide with Alcohols: Synthesis of Quinolines via Hydrogen Borrowing Strategy and their Mechanistic Studies

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