P-arylation of aryl halides by an environmentally compatible method

Sobhani, Sara; Vahidi, Zahra

doi:10.1139/cjc-2017-0364

Cited by 4 publications

(1 citation statement)

References 43 publications

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“…At first, the Pd complex of an “ NNN ” princer ligand (BIP) supported on nanomagnetic γ-Fe 2 O 3 @SiO 2 was prepared, which proved to be a good catalyst in the cross-coupling reaction of diethyl phosphite and iodobenzene under solvent-free conditions [ 166 ]. The Pd complex of 2-aminothiophenol (Pd-2-ATP-γ-Fe 2 O 3 ) [ 167 ] and DABCO (Pd-DABCO-γ-Fe 2 O 3 ) [ 168 ] could be used as a catalyst in pure water, or in sodium dodecyl sulfate (SDS) aqueous micellar solution. The heterogeneous catalysts could be reused in five or six consecutive cycles, without any significant loss in their catalytic activity.…”

Section: Novel Developments On the Hirao Reactionmentioning

confidence: 99%

New Developments on the Hirao Reactions, Especially from “Green” Point of View

Henyecz

Keglevich

2019

COS

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Background: The Hirao reaction discovered ca. 35 years ago is an important P–C coupling protocol between dialkyl phosphites and aryl halides in the presence of Pd(PPh3)4 as the catalyst and a base to provide aryl phosphonates. Then, the reaction was extended to other Preagents, such as secondary phosphine oxides and H-phosphinates and to other aryl and hetaryl derivatives to afford also phosphinic esters and tertiary phosphine oxides. Instead of the Pd(PPh3)4 catalyst, Pd(OAc)2 and Ni-salts were also applied as catalyst precursors together with a number of mono- and bidentate P-ligands. Objective: In our review, we undertook to summarize the target reaction with a special stress on the developments attained in the last 6 years, hence this paper is an update of our earlier reviews in a similar topic. Conclusion: “Greener” syntheses aimed at utilizing phase transfer catalytic and microwave-assisted approaches, even under “P-ligand-free. or even solvent-free conditions are the up-to date versions of the classical Hirao reaction. The mechanism of the reaction is also in the focus these days.

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Section: Novel Developments On the Hirao Reactionmentioning

confidence: 99%

New Developments on the Hirao Reactions, Especially from “Green” Point of View

Henyecz

Keglevich

2019

COS

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Fe₃O₄@glutamate MOF functionalized with Co nanoparticles anchored dicyandiamde: As a capable heterogeneous and reusable nanocatalyst in C–P cross‐coupling reaction

Eftekhar

Khosravi

2022

Applied Organom Chemis

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Herein, we report an efficient, simple, coherent, and green benign synthesis of the C–P coupling reaction based on the Fe3O4@glutamate MOF functionalized with Co nanoparticle anchored dicyandiamide. The structure of the as‐prepared catalyst was characterized by a series of measurement techniques, including FT‐IR, XRD, BET, TEM, FE‐SEM, EDX, EDX‐mapping, VSM, TGA, and ICP‐OES. The aforementioned nanocatalyst with a unique structure exhibited excellent catalytic performance on various substrates towards the synthesis of C–P cross‐coupled products in good to high yields under mild conditions. This unique heterogeneous catalytic system kept relatively high catalytic activity after five recycle runs under the same reaction conditions.

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Designing of Ferromagnetic 3D Hierarchical Core‐Shell Fe₃O₄@NiO/Co₃O₄ Microspheres Derived from a MOF Precursor: As an Efficient Catalyst for C‐P Cross Coupling Reaction

Mohammadinezhad

Akhlaghinia

2019

ChemistrySelect

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Herein, we report the synthesis of a 3D hierarchical heterostructure microsphere through a facile solvothermal and hydrothermal method followed by an annealing treatment. The obtained ternary core‐shell nanostructured was comprehensively characterized by means of variety techniques including FT‐IR, XRD, BET, TEM, FE‐SEM, EDX, EDX‐mapping, VSM and ICP‐OES. It was found that this hierarchical nanostructured could promote the C−P cross coupling reaction of a large library of functional substrates. Benefiting from the unique hierarchical architecture and the synergistic effect among multiple components resulted from the coexistence of micro‐, meso‐ and macropores as well as its small nano‐crystallite size (20‐71 nm), this novel catalyst revealed superior catalytic performance in the C−P cross coupling reaction. More importantly, the ferromagnetic behavior of 3D hierarchical core‐shell Fe3O4@NiO/Co3O4 microspheres is responsible for easy separation from the reaction mixture using an external magnetic field and its long term‐durability under reaction conditions even after nine consecutive recycle runs.

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P-arylation of aryl halides by an environmentally compatible method

Cited by 4 publications

References 43 publications

New Developments on the Hirao Reactions, Especially from “Green” Point of View

New Developments on the Hirao Reactions, Especially from “Green” Point of View

Fe₃O₄@glutamate MOF functionalized with Co nanoparticles anchored dicyandiamde: As a capable heterogeneous and reusable nanocatalyst in C–P cross‐coupling reaction

Designing of Ferromagnetic 3D Hierarchical Core‐Shell Fe₃O₄@NiO/Co₃O₄ Microspheres Derived from a MOF Precursor: As an Efficient Catalyst for C‐P Cross Coupling Reaction

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P-arylation of aryl halides by an environmentally compatible method

Cited by 4 publications

References 43 publications

New Developments on the Hirao Reactions, Especially from “Green” Point of View

New Developments on the Hirao Reactions, Especially from “Green” Point of View

Fe3O4@glutamate MOF functionalized with Co nanoparticles anchored dicyandiamde: As a capable heterogeneous and reusable nanocatalyst in C–P cross‐coupling reaction

Designing of Ferromagnetic 3D Hierarchical Core‐Shell Fe3O4@NiO/Co3O4 Microspheres Derived from a MOF Precursor: As an Efficient Catalyst for C‐P Cross Coupling Reaction

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Fe₃O₄@glutamate MOF functionalized with Co nanoparticles anchored dicyandiamde: As a capable heterogeneous and reusable nanocatalyst in C–P cross‐coupling reaction

Designing of Ferromagnetic 3D Hierarchical Core‐Shell Fe₃O₄@NiO/Co₃O₄ Microspheres Derived from a MOF Precursor: As an Efficient Catalyst for C‐P Cross Coupling Reaction