Methyl-transfer reaction to alkylthiol catalyzed by a simple vitamin B 12 model complex using zinc powder

Ling Pan; Keishiro Tahara; Takahiro Masuko; Yoshio Hisaeda

doi:10.1016/j.ica.2011.01.004

Methyl-transfer reaction to alkylthiol catalyzed by a simple vitamin B ₁₂ model complex using zinc powder

Ling Pan, Keishiro Tahara, Takahiro Masuko, Yoshio Hisaeda

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12 Citations (Scopus)

Abstract

The catalytic methyl-transfer reaction from methyl tosylate to 1-octanethiol was carried out in the presence of a simple vitamin B₁₂ model complex, [Co(III){(C₂C₃)(DO)(DOH)pn}Br ₂], with zinc powder as the reducing reagent at 50°C. Such a catalytic reaction proceeded via the formation and dissociation of a cobalt-carbon bond in the simple vitamin B₁₂ model complex under non-enzymatic conditions. The mechanism for the methyl-transfer reaction was investigated by electronic and mass spectroscopies. The Co(I) species, which is generated from the reduction of the catalyst by the zinc powder, and its methylated CH₃-Co complex were found to be indispensable intermediates.

Original language	English
Pages (from-to)	194-199
Number of pages	6
Journal	Inorganica Chimica Acta
Volume	368
Issue number	1
DOIs	https://doi.org/10.1016/j.ica.2011.01.004
Publication status	Published - Mar 15 2011

All Science Journal Classification (ASJC) codes

Physical and Theoretical Chemistry
Inorganic Chemistry
Materials Chemistry

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10.1016/j.ica.2011.01.004

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title = "Methyl-transfer reaction to alkylthiol catalyzed by a simple vitamin B 12 model complex using zinc powder",

abstract = "The catalytic methyl-transfer reaction from methyl tosylate to 1-octanethiol was carried out in the presence of a simple vitamin B12 model complex, [Co(III){(C2C3)(DO)(DOH)pn}Br 2], with zinc powder as the reducing reagent at 50°C. Such a catalytic reaction proceeded via the formation and dissociation of a cobalt-carbon bond in the simple vitamin B12 model complex under non-enzymatic conditions. The mechanism for the methyl-transfer reaction was investigated by electronic and mass spectroscopies. The Co(I) species, which is generated from the reduction of the catalyst by the zinc powder, and its methylated CH3-Co complex were found to be indispensable intermediates.",

author = "Ling Pan and Keishiro Tahara and Takahiro Masuko and Yoshio Hisaeda",

note = "Funding Information: The present work was partially supported by a Grant-in-Aid for Scientific Research on Priority Areas “Chemistry of Concerto Catalysis” and Global COE Program “Science for Future Molecular Systems” from the Ministry of Education, Culture, Sports, Science and Technology (MEXT) of Japan, and a Grant-in-Aid for Scientific Research (A) ( 21245016 ) from the Japan Society for the Promotion of Science (JSPS). This work was also supported by Science Foundation for Young Teachers of Northeast Normal University ( 09 QNJJ017 ) (to L.P.). ",

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AU - Masuko, Takahiro

AU - Hisaeda, Yoshio

N1 - Funding Information: The present work was partially supported by a Grant-in-Aid for Scientific Research on Priority Areas “Chemistry of Concerto Catalysis” and Global COE Program “Science for Future Molecular Systems” from the Ministry of Education, Culture, Sports, Science and Technology (MEXT) of Japan, and a Grant-in-Aid for Scientific Research (A) ( 21245016 ) from the Japan Society for the Promotion of Science (JSPS). This work was also supported by Science Foundation for Young Teachers of Northeast Normal University ( 09 QNJJ017 ) (to L.P.).

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AB - The catalytic methyl-transfer reaction from methyl tosylate to 1-octanethiol was carried out in the presence of a simple vitamin B12 model complex, [Co(III){(C2C3)(DO)(DOH)pn}Br 2], with zinc powder as the reducing reagent at 50°C. Such a catalytic reaction proceeded via the formation and dissociation of a cobalt-carbon bond in the simple vitamin B12 model complex under non-enzymatic conditions. The mechanism for the methyl-transfer reaction was investigated by electronic and mass spectroscopies. The Co(I) species, which is generated from the reduction of the catalyst by the zinc powder, and its methylated CH3-Co complex were found to be indispensable intermediates.

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Methyl-transfer reaction to alkylthiol catalyzed by a simple vitamin B ₁₂ model complex using zinc powder

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