Phase-transfer-mediated electrochemical reaction: anodic disulfide bond formation under biphasic condition

Phase-transfer-mediated electrochemical reaction: anodic disulfide bond formation under biphasic condition

[Display omitted] The use of bromide ion as a redox mediator promotes electrochemical reactions in the non-conductive cyclohexane phase. Anodically oxidized species of bromide ion in the conductive methanol phase can bring oxidizing power across phases to induce oxidative disulfide bond formation of...

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Bibliographic Details
Published in:Tetrahedron letters Vol. 55; no. 26; pp. 3622 - 3624
Main Authors: Takahashi, Masahito, Okada, Yohei, Kitano, Yoshikazu, Chiba, Kazuhiro
Format: Journal Article
Language:English
Published: Elsevier Ltd 25-06-2014
Subjects:
Anodic
Anodic disulfide bond
Anodizing
Biphasic
Bonding
Bromide ion
Bromides
Cyclohexane
Disulfides
Methyl alcohol
Phase-transfer mediator
Tetrahedrons
Phase-transfer mediator
Anodic disulfide bond
Biphasic
Bromide ion
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Summary:[Display omitted] The use of bromide ion as a redox mediator promotes electrochemical reactions in the non-conductive cyclohexane phase. Anodically oxidized species of bromide ion in the conductive methanol phase can bring oxidizing power across phases to induce oxidative disulfide bond formation of a hydrophobically-tagged tripeptide, which is located predominantly in the cyclohexane phase. In addition to commonly used tetraalkylammonium salts, inorganic sodium salt can also be effective alternatives for the bromide source.
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content type line 23
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2014.04.116