Dataset Information

Synthesis of Nanosheets Containing Uniformly Dispersed Pd^II Ions at an Aqueous/Aqueous Interface: Development of a Highly Active Nanosheet Catalyst for Mizoroki-Heck Reaction.

ABSTRACT: A method was developed to synthesize a nanosheet at the interface of an aqueous layer of Pd^II ions and an aqueous layer of hydrophilic polymer bearing a metal coordination unit (HPMC). The nanosheet was synthesized through generation of an interface by the addition of an aqueous solution of Pd^II ions with a low specific gravity (1.03 g/cm³) to a dispersed aqueous solution of HPMC with a high specific gravity (1.50 g/cm³), resulting in rapid cross-linking at the interface. An electron probe microanalysis mapping image showed that the Pd^II ions were uniformly dispersed in the nanosheet. The nanosheet showed a high catalyst activity for the Mizoroki-Heck cross-coupling reaction with a turnover number (TON) and turnover frequency (TOF) greater than 3,333,333 and 138,889 h^-1, respectively. These are the greatest TON and TOF values reported for heterogeneous polymeric catalysts for the Mizoroki-Heck reaction.

SUBMITTER: Nagai D

PROVIDER: S-EPMC7391948 | biostudies-literature | 2020 Jul

REPOSITORIES: biostudies-literature

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Synthesis of Nanosheets Containing Uniformly Dispersed PdII Ions at an Aqueous/Aqueous Interface: Development of a Highly Active Nanosheet Catalyst for Mizoroki-Heck Reaction.

Nagai Daisuke D Morita Moeko M Yamanobe Takeshi T

ACS omega 20200716 29

A method was developed to synthesize a nanosheet at the interface of an aqueous layer of PdII ions and an aqueous layer of hydrophilic polymer bearing a metal coordination unit (HPMC). The nanosheet was synthesized through generation of an interface by the addition of an aqueous solution of PdII ions with a low specific gravity (1.03 g/cm3) to a dispersed aqueous solution of HPMC with a high specific gravity (1.50 g/cm3), resulting in rapid cross-linki ...[more]

PMID: 32743226

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Project description:The formation of a C-C bond through Mizoroki-Heck cross-coupling reactions in water with efficient heterogeneous catalysts is a challenging task. In this current study, a highly reduced graphene oxide (HRG) immobilized palladium (Pd) nanoparticle based catalyst (HRG-Py-Pd) is used to catalyze Mizoroki-Heck cross-coupling reactions in water. During the preparation of the catalyst, amino pyrene is used as a smart functionalizing ligand, which offered chemically specific binding sites for the effective and homogeneous nucleation of Pd NPs on the surface of HRG, which significantly enhanced the physical stability and dispersibility of the resulting catalyst in an aqueous medium. Microscopic analysis of the catalyst revealed a uniform distribution of ultrafine Pd NPs on a solid support. The catalytic properties of HRG-Py-Pd are tested towards the Mizoroki-Heck cross-coupling reactions of various aryl halides with acrylic acid in an aqueous medium. Furthermore, the catalytic efficacy of HRG-Py-Pd is also compared with its non-functionalized counterparts such as HRG-Pd and pristine Pd NPs (Pd-NPs). Using the HRG-Py-Pd nanocatalyst, the highest conversion of 99% is achieved in the coupling reaction of 4-bromoanisol and acrylic acid in an aqueous solution in a relatively short period of time (3 h), with less quantity of catalyst (3 mg). Comparatively, pristine Pd NPs delivered lower conversion (∼92%) for the same reaction required a long reaction time and a large amount of catalyst (5.3 mg). Indeed, the conversion of the reaction further decreased to just 40% when 3 mg of Pd-NPs was used which was sufficient to produce 99% conversion in the case of HRG-Py-Pd. On the other hand, HRG-Pd did not deliver any conversion and was ineffective even after using a high amount of catalyst and a longer reaction time. The inability of the HRG-Pd to promote coupling reactions can be attributed to the agglomeration of Pd NPs which reduced the dispersion quality of the catalyst in water. Therefore, the high aqueous stability of HRG-Py-Pd due to smart functionalization can be utilized to perform other organic transformations in water which was otherwise not possible.

Dataset Information

Synthesis of Nanosheets Containing Uniformly Dispersed Pd^II Ions at an Aqueous/Aqueous Interface: Development of a Highly Active Nanosheet Catalyst for Mizoroki-Heck Reaction.

Publications

Synthesis of Nanosheets Containing Uniformly Dispersed Pd<sup>II</sup> Ions at an Aqueous/Aqueous Interface: Development of a Highly Active Nanosheet Catalyst for Mizoroki-Heck Reaction.

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