Nickel-metalated porous organic polymer for Suzuki–Miyaura cross-coupling reaction

Dong, Ying; Jv, Jing-Jing; Li, Yue; Li, Wen-Han; Chen, Yun-Qi; Sun, Qian; Ma, Jian‐Ping; Dong, Yu‐Bin

doi:10.1039/c9ra03679b

Cited by 14 publications

(9 citation statements)

References 56 publications

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“…Such a stable network appear to be well-suited to the strong basic conditions used in the homogeneous Ni-catalyzed benzothiophene C–H arylation reaction . Furthermore, POP-type materials were already reported for the immobilization of nickel catalyst for the ethylene oligomerization, or for Suzuki-Miyaura coupling …”

Section: Introductionmentioning

confidence: 99%

“…27 Furthermore, POP-type materials were already reported for the immobilization of nickel catalyst for the ethylene oligomerization, 34 or for Suzuki-Miyaura coupling. 35 While proof-of-concept heterogeneous C−H activation catalysts were recently published by the group of Yamada for palladium-catalyzed thiophene arylation 36 and by the group of Sawamura for nickel-catalyzed benzoxazole arylation, 37 a general protocol is still missing.…”

Section: Introductionmentioning

confidence: 99%

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Heterogenization of a Molecular Ni Catalyst within a Porous Macroligand for the Direct C–H Arylation of Heteroarenes

et al. 2021

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Direct C-H functionalization catalyzed by a robust and recyclable heterogeneous catalyst is highly desirable for sustainable fine chemical synthesis. Bipyridine units covalently incorporated into the backbone of a porous organic polymer were used as a porous macroligand for the heterogenization of a molecular nickel catalyst. A controlled nickel loading within the porous macroligand is achieved and the nickel coordination to the bpy sites is assessed at the molecular level using IR and solid-state NMR spectroscopy. The heterogenized Ni-bpy catalyst was successfully applied to the direct and fully selective C2 arylation of benzothiophenes, thiophene and selenophene, as well as for the arylation of free NH-indole. Recyclability of the catalyst was achieved by employing hydride activators to reach a cumulative turnover number of more than 300 after seven cycles of catalysis, which corresponds to a total productivity of 12 grams of 2-phenylbenzothiophene, chosen as model target biaryl, per gram of catalyst.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Heterogenization of a Molecular Ni Catalyst within a Porous Macroligand for the Direct C–H Arylation of Heteroarenes

et al. 2021

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“…In pursuit of a sustainable alternative to the Pd catalysts, a porous organic polymer-based Ni(II)-α-diimine was successfully synthesized and used in SMC of various aryl halides and boronic acids. 76 …”

Section: Introductionmentioning

confidence: 99%

Ligand Steric Effects of α-Diimine Nickel(II) and Palladium(II) Complexes in the Suzuki–Miyaura Cross-Coupling Reaction

et al. 2020

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Nickel catalysts represent a low cost and environmentally friendly alternative to palladium-based catalytic systems for Suzuki–Miyaura cross-coupling (SMC) reactions. However, nickel catalysts have suffered from poor air, moisture, and thermal stabilities, especially at high catalyst loading, requiring controlled reaction conditions. In this report, we examine a family of mono- and dinuclear Ni(II) and Pd(II) complexes with a diverse and versatile α-diimine ligand environment for SMC reactions. To evaluate the ligand steric effects, including the bite angle in the reaction outcomes, the structural variation of the complexes was achieved by incorporating iminopyridine- and acenaphthene-based ligands. Moreover, the impact of substrate bulkiness was investigated by reacting various aryl bromides with phenylboronic acid, 2-naphthylboronic acid, and 9-phenanthracenylboronic acid. Yields were the best with the dinuclear complex, being nearly quantitative (93–99%), followed by the mononuclear complexes, giving yields of 78–98%. Consequently, α-diimine-based ligands have the potential to deliver Ni-based systems as sustainable catalysts in SMC.

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“…47,48 However, Ni is sensitive to solvent, a greater amount is needed, and severe catalytic conditions are usually required. [49][50][51][52][53][54][55][56][57][58][59][60][61][62][63][64][65] The combination of the advantages of Pd and Ni for catalyzing the coupling reaction has recently attracted tremendous attention. 66 The design of ordered, more cost-effective and eco-friendly forms to adjust catalytic properties and elucidate synergy is greatly needed.…”

Section: Introductionmentioning

confidence: 99%

Terpyridine-based Pd(ii)/Ni(ii) organometallic framework nano-sheets supported on graphene oxide—investigating the fabrication, tuning of catalytic properties and synergetic effects

Ren

Wang

et al. 2020

RSC Adv.

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Nickel-metalated porous organic polymer for Suzuki–Miyaura cross-coupling reaction

Abstract: A porous organic polymer with Ni(ii) α-diimine moiety, which can be a highly active reusable heterogeneous catalyst to promote the Suzuki–Miyaura coupling reaction, was reported.

Cited by 14 publications

References 56 publications

Heterogenization of a Molecular Ni Catalyst within a Porous Macroligand for the Direct C–H Arylation of Heteroarenes

Heterogenization of a Molecular Ni Catalyst within a Porous Macroligand for the Direct C–H Arylation of Heteroarenes

Ligand Steric Effects of α-Diimine Nickel(II) and Palladium(II) Complexes in the Suzuki–Miyaura Cross-Coupling Reaction

Terpyridine-based Pd(ii)/Ni(ii) organometallic framework nano-sheets supported on graphene oxide—investigating the fabrication, tuning of catalytic properties and synergetic effects

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