Methyl-transfer reaction to alkylthiol catalyzed by a simple vitamin B12 model complex using zinc powder

Pan, Ling; Tahara, Keishiro; Masuko, Takahiro; Hisaeda, Yoshio

doi:10.1016/j.ica.2011.01.004

Cited by 10 publications

(8 citation statements)

References 36 publications

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“…The Zn plate was used as a sacrificial anode and the resultant Zn 2+ ions was vital for the activation of 1-octanethiol [ 76 ]. A similar reaction was successfully mediated by the imine/oxime-type cobalt complex 2a using zinc powder [ 77 ].…”

Section: Reviewmentioning

confidence: 99%

Learning from B₁₂ enzymes: biomimetic and bioinspired catalysts for eco-friendly organic synthesis

Tahara¹,

Pan²,

Ono³

et al. 2018

Beilstein J. Org. Chem.

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Cobalamins (B12) play various important roles in vivo. Most B12-dependent enzymes are divided into three main subfamilies: adenosylcobalamin-dependent isomerases, methylcobalamin-dependent methyltransferases, and dehalogenases. Mimicking these B12 enzyme functions under non-enzymatic conditions offers good understanding of their elaborate reaction mechanisms. Furthermore, bio-inspiration offers a new approach to catalytic design for green and eco-friendly molecular transformations. As part of a study based on vitamin B12 derivatives including heptamethyl cobyrinate perchlorate, we describe biomimetic and bioinspired catalytic reactions with B12 enzyme functions. The reactions are classified according to the corresponding three B12 enzyme subfamilies, with a focus on our recent development on electrochemical and photochemical catalytic systems. Other important reactions are also described, with a focus on radical-involved reactions in terms of organic synthesis.

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Section: Reviewmentioning

confidence: 99%

Learning from B₁₂ enzymes: biomimetic and bioinspired catalysts for eco-friendly organic synthesis

Tahara¹,

Pan²,

Ono³

et al. 2018

Beilstein J. Org. Chem.

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“…Chemical synthesis employs zinc powder on a widespread basis as a low-cost common catalyst with high catalytic efficiency. [17][18][19] Based on the substantial reducibility of zinc atom to acetenyl, 20 Shen et al successfully synthesised PSA resin by Zn powder catalysis. 21 Compared with the above three methods, the zinc powder catalytic method has the following advantages: (1) zinc powder is cheap and readily available; (2) the synthesis step is simple; (3) reaction process does not give off much heat intensively; (4) no gas release; and (5) the synthetic resin has low viscosity and excellent processing performance.…”

Section: Introductionmentioning

confidence: 99%

Study on vinyl crosslinking and related properties of silicon-containing arylacetylene resin synthesised by zinc powder catalysis

Dong

Chen

Wang

et al. 2022

High Performance Polymers

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A matrix resin poly(silicon-containing arylacetylene vinyl)s (PSAV) containing vinyl at both branch and terminal chains underwent synthesis via the zinc powder catalytic method using m-diacetylene benzene and dichloromethylvinylsilane as raw materials. Vinyl in the PSAV resin was crosslinked by the free radical initiator dibenzoyl peroxide to obtain a crosslinked network structure resin (PSAV-L). This approach sought to improve the thermal properties and other related properties of the matrix resin. A series of tests, such as rotated rheometer, FTIR, DSC, TGA, Py-GC-MS and universal testing machine, characterised processing property, curing behaviour, thermal properties and mechanical properties. The rheological curve shows that PSAV-L resin has a wide processing window (40–134.5°C), endowing the resin with excellent processing performance. Thermal curing behaviour indicates that PSAV-L resin can start curing at a lower temperature, namely, 32°C earlier than PSAV resin. TGA analysis shows that the degradation temperature at 5% weight loss (Td5) of PSAV-L resin stands at 579.4°C, 45.4°C higher than that of PSAV resin due to the fact that the crosslinking of vinyl gives PSAV-L resin a network structure. The flexural strength, flexural modulus and ILSS of the quartz fibre cloth reinforced PSAV-L resin composite (QF/PSAV-L) are 184.68 MPa, 15.50 GPa and 12.40 MPa. The PSAV-L resin exhibits the comprehensive properties of good processing performance, low curing temperature, excellent thermal performance and high mechanical properties.

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“…The beautiful and fascinating structure of vitamin B 12 (cobalamin), the most complex nonpolymeric compound found in nature, is synthesized by certain bacteria. − It is quite amazing that a humble microorganism can make a molecule with the complexity of vitamin B 12 . Thus, the catalytic activity of this metalloenzyme is very important and interesting in organic synthesis and catalytic research. − The term “vitamin B 12 ” refers to four compounds (cyano-, hydroxo-, methyl-, and adenosylcobalamin) . This water-soluble vitamin is a biologically active corrinoid, a natural Co-complex, and highly functionalized .…”

Section: Introductionmentioning

confidence: 99%

Use of Vitamin B₁₂ as a Nontoxic and Natural Catalyst for the Synthesis of Benzoxazoles via Catechols and Primary Amines in Water under Aerobic Oxidation

Sharghi

Hosseini

Aboonajmi

et al. 2021

ACS Sustainable Chem. Eng.

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We report an efficient and environmentally friendly approach for the synthesis of benzoxazoles in water using vitamin B 12 (2 mol %) as a nontoxic and natural catalyst under ambient air as the oxidant. To achieve this goal, benzoxazoles were prepared in relatively high yields by the reaction of catechols with amines under air at 50 °C in the presence of vitamin B 12 . This work is the first report on the incorporation of a natural cobalt complex as a redox catalyst for the oxidation of catechols. Also, we applied gabapentin and tranexamic acid, with an amine functional group, known as to have anticonvulsant and analgesic activity and to prevent heavy bleeding, for the synthesis of benzoxazoles with good results. The significant features of this procedure for the preparation of benzoxazoles include the use of water as a green and attractive solvent in an organic reaction, the use of ambient air as a benign sole oxidant due to its abundance, low cost, mild conditions, environmentally friendly, the use of a biodegradable catalyst, no moisture sensitivity, simple workup procedure, and simple recovery and recyclability of the catalyst without a significant decrease in activity, which all together make this approach in line with the 12 principles of green chemistry. These aforementioned features make the current approach attractive for academic research as well as industrial applications.

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Methyl-transfer reaction to alkylthiol catalyzed by a simple vitamin B12 model complex using zinc powder

Cited by 10 publications

References 36 publications

Learning from B₁₂ enzymes: biomimetic and bioinspired catalysts for eco-friendly organic synthesis

Learning from B₁₂ enzymes: biomimetic and bioinspired catalysts for eco-friendly organic synthesis

Study on vinyl crosslinking and related properties of silicon-containing arylacetylene resin synthesised by zinc powder catalysis

Use of Vitamin B₁₂ as a Nontoxic and Natural Catalyst for the Synthesis of Benzoxazoles via Catechols and Primary Amines in Water under Aerobic Oxidation

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Methyl-transfer reaction to alkylthiol catalyzed by a simple vitamin B12 model complex using zinc powder

Cited by 10 publications

References 36 publications

Learning from B12 enzymes: biomimetic and bioinspired catalysts for eco-friendly organic synthesis

Learning from B12 enzymes: biomimetic and bioinspired catalysts for eco-friendly organic synthesis

Study on vinyl crosslinking and related properties of silicon-containing arylacetylene resin synthesised by zinc powder catalysis

Use of Vitamin B12 as a Nontoxic and Natural Catalyst for the Synthesis of Benzoxazoles via Catechols and Primary Amines in Water under Aerobic Oxidation

Contact Info

Product

Resources

About

Learning from B₁₂ enzymes: biomimetic and bioinspired catalysts for eco-friendly organic synthesis

Learning from B₁₂ enzymes: biomimetic and bioinspired catalysts for eco-friendly organic synthesis

Use of Vitamin B₁₂ as a Nontoxic and Natural Catalyst for the Synthesis of Benzoxazoles via Catechols and Primary Amines in Water under Aerobic Oxidation