Application of Curcumin as Ligand in [Pd(Curc‐H)<sub>2</sub>] Catalyst for Carbon‐Carbon Bond Formation in Heck and Suzuki Coupling Reactions

Bhange, Dattatraya S.; Rasal, Nishant K.; Sonawane, Ravindra S.; Jagtap, Sangeeta V.

doi:10.1002/slct.201802420

Cited by 5 publications

(3 citation statements)

References 64 publications

(38 reference statements)

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“…As a part of our research efforts to develop novel, simple and cheap ligands and catalytic methods using transition metal catalyzed coupling reactions; we have reported, new synthetic method that has been developed for selective mono‐ N ‐alkylation of amines to synthesize 2‐(arylamino)ethanols and 2‐aryloxyethanols and use of curcumin as ligand in [Pd(Curc‐H) 2 ] catalyst for C−C bond formation in Heck and Suzuki coupling reactions …”

Section: Methodsmentioning

confidence: 99%

Application of N‐Aryl Ethanolamines as N,O‐Ligand in Nickel(II)‐Catalyzed Carbon‐Carbon Bond Formation in Heck Coupling Reactions

et al. 2020

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A simple and efficient protocol of Ni‐(II) catalyzed C−C bond formation in Heck coupling reactions of a variety of alkenes and aryl and hetero aryl halides, using various N‐aryl ethanolamines as bi‐dentate N,O‐ligand with moderate to excellent yields is described here. The application of different N‐aryl ethanolamines in presence of NiCl2.6H2O catalyst is tested for C−C bond formation in Heck reactions and found to be efficient in homogeneous medium. This simple and efficient protocol shows a broad substrate scope for substituted alkenes, aryl and hetero aryl halides and tolerates various functional groups and successfully demonstrated by 31 examples.

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Section: Methodsmentioning

confidence: 99%

Application of N‐Aryl Ethanolamines as N,O‐Ligand in Nickel(II)‐Catalyzed Carbon‐Carbon Bond Formation in Heck Coupling Reactions

et al. 2020

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“…(E)-1,2-Di-p-tolylethene (E-1e). 23 E-1e was prepared with 4methylbenzaldehyde (2.5 mmol, 300 mg, 294 μL) as the substrate according to general procedure A as a white solid (218.4 mg, 84% yield, mp = 179.8−181.8 °C). 1 H NMR (400 MHz, CDCl 3 ) δ ppm 7.44 (d, J = 8 Hz, 4H), 7.20 (d, J = 8 Hz, 4H), 7.08 (s, 2H), 2.40 (s, 6H).…”

Section: ■ Conclusionmentioning

confidence: 99%

Energy-Transfer-Mediated Photocatalysis by a Bioinspired Organic Perylenephotosensitizer HiBRCP

Zhang

Xia

et al. 2021

J. Org. Chem.

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Energy transfer plays a special role in photocatalysis by utilizing the potential energy of the excited state through indirect excitation, in which a photosensitizer determines the thermodynamic feasibility of the reaction. Bioinspired by the energy-transfer ability of natural product cercosporin, here we developed a green and highly efficient organic photosensitizer HiBRCP (hexaisobutyryl reduced cercosporin) through structural modification of cercosporin. After structural manipulation, its triplet energy was greatly improved, and then, it could markedly promote the efficient geometrical isomerization of alkenes from the E-isomer to the Z-isomer. Moreover, it was also effective for energy-transfer-mediated organometallic catalysis, which allowed realization of the cross-coupling of aryl bromides and carboxylic acids through efficient energy transfer from HiBRCP to nickel complexes. Thus, the study on the relationship between structural manipulation and their photophysical properties provided guidance for further modification of cercosporin, which could be applied to more meaningful and challenging energy-transfer reactions.

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“…A good deal of knowledge about the synthesis of phosphine complexes, especially with palladium and platinum metals, has been extensively documented . Ever since phosphapalladacycles were highlighted by Herrmann for the Heck and Suzuki reactions, various kinds of phosphorus‐,1a nitrogen‐, sulfur‐ and oxygen‐derived palladacycles have emerged as promising catalysts with high turnover numbers (TONs) in numerous CC coupling reactions.…”

Section: Introductionmentioning

confidence: 99%

Mono‐ and dinuclear oxime palladacycles bearing diphosphine ligands: An unusual coordination mode for dppe

Samiee

Shiralinia

Hoveizi

et al. 2019

Applied Organom Chemis

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Three new oxime‐based palladacycles, namely [Pd{C,N‐C6H4{C(Me)NOH}‐2}(dppm)]ClO4 (1), [Pd2{C,N‐C6H4{C(Me)NOH}‐2}2(dppe)2(μ‐dppe)](ClO4)2 (2) and [Pd{C,N‐C6H4{C(Me)NOH}‐2}(dppmS2)]ClO4 (3), were synthesized by the reaction of dinuclear oxime complex [Pd{C,N‐C6H4{C(Me)NOH}‐2}(μ‐Cl)]2 with different diphosphine ligands (dppm, dppe and dppmS2). The synthesized complexes were characterized using Fourier transform infrared, 31P NMR, 1H NMR and 13C NMR spectroscopic methods and elemental analyses, and their molecular structures were elucidated using X‐ray crystallography. The structure of 2 is worthy of note as it is the first oxime palladacycle where there are both bridging (P–) and chelating (P^P) dppe ligands, giving rise to a dinuclear complex. The palladium atom is in a five‐coordinate, square pyramidal P3NC environment, while in 3 the palladium atom is in a distorted square planar environment, coordinated by the oxime ligand and a chelating (S^S) dppmS2 ligand. These complexes were employed as efficient catalysts for the Suzuki–Miyaura cross‐coupling reaction of several aryl bromides with phenylboronic acid. The in vitro cytotoxicity of the compounds was also evaluated against human tumour cell lines (HT29, A549 and HeLa) using the MTT assay method. The results indicate that the dinuclear complex 2 has greater catalytic and anticancer activity in comparison with the mononuclear complexes 1 and 3.

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Application of Curcumin as Ligand in [Pd(Curc‐H)₂] Catalyst for Carbon‐Carbon Bond Formation in Heck and Suzuki Coupling Reactions

Cited by 5 publications

References 64 publications

Application of N‐Aryl Ethanolamines as N,O‐Ligand in Nickel(II)‐Catalyzed Carbon‐Carbon Bond Formation in Heck Coupling Reactions

Application of N‐Aryl Ethanolamines as N,O‐Ligand in Nickel(II)‐Catalyzed Carbon‐Carbon Bond Formation in Heck Coupling Reactions

Energy-Transfer-Mediated Photocatalysis by a Bioinspired Organic Perylenephotosensitizer HiBRCP

Mono‐ and dinuclear oxime palladacycles bearing diphosphine ligands: An unusual coordination mode for dppe

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Application of Curcumin as Ligand in [Pd(Curc‐H)2] Catalyst for Carbon‐Carbon Bond Formation in Heck and Suzuki Coupling Reactions

Cited by 5 publications

References 64 publications

Application of N‐Aryl Ethanolamines as N,O‐Ligand in Nickel(II)‐Catalyzed Carbon‐Carbon Bond Formation in Heck Coupling Reactions

Application of N‐Aryl Ethanolamines as N,O‐Ligand in Nickel(II)‐Catalyzed Carbon‐Carbon Bond Formation in Heck Coupling Reactions

Energy-Transfer-Mediated Photocatalysis by a Bioinspired Organic Perylenephotosensitizer HiBRCP

Mono‐ and dinuclear oxime palladacycles bearing diphosphine ligands: An unusual coordination mode for dppe

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Application of Curcumin as Ligand in [Pd(Curc‐H)₂] Catalyst for Carbon‐Carbon Bond Formation in Heck and Suzuki Coupling Reactions