Dialling-in new reactivity into the Shono-type anodic oxidation reaction

Research output: Contribution to journalArticlepeer-review

Standard

Dialling-in new reactivity into the Shono-type anodic oxidation reaction. / Jones, Alan M.

In: The Chemical Record, 04.11.2020.

Research output: Contribution to journalArticlepeer-review

Harvard

APA

Vancouver

Author

Bibtex

@article{1aa3360f91444e769d96e202c2db576a,
title = "Dialling-in new reactivity into the Shono-type anodic oxidation reaction",
abstract = "This Personal Account describes the author's groups{\textquoteright} research in the field of electrosynthetic anodic oxidation, beginning with initial trial and error attempts with the Shono oxidation. Early setbacks with complex rotameric amide mixtures, provided the ideal environment for the discovery of the Oxa‐Shono reaction‐Osp2‐Csp3 bond cleavage of esters‐providing two useful products in one‐step: aldehyde selective oxidation level products and a mild de‐esterification method to afford carboxylic acids in the process. The development of the Oxa‐Shono reaction provided the impetus for the discovery of other electrically propelled‐Nsp2‐Csp2 and Nsp2‐Csp3‐bond breaking reactions in bioactive amide and sulfonamide systems. Understanding the voltammetric behaviour of the molecule under study, switching between controlled current‐ or controlled potential‐ electrolysis, and restricting electron flow (the reagent), affords exquisite control over the reaction outcomes in batch and flow. Importantly, this bio‐inspired advance in electrosynthetic dealkylation chemistry mimics the metabolic outcomes observed in nature.",
keywords = "Anodic oxidation, bond cleavage, dealkylation, electrosynthesis, Shono",
author = "Jones, {Alan M}",
year = "2020",
month = nov,
day = "4",
doi = "10.1002/tcr.202000116",
language = "English",
journal = "The Chemical Record",
issn = "1527-8999",
publisher = "Chemical Society of Japan",

}

RIS

TY - JOUR

T1 - Dialling-in new reactivity into the Shono-type anodic oxidation reaction

AU - Jones, Alan M

PY - 2020/11/4

Y1 - 2020/11/4

N2 - This Personal Account describes the author's groups’ research in the field of electrosynthetic anodic oxidation, beginning with initial trial and error attempts with the Shono oxidation. Early setbacks with complex rotameric amide mixtures, provided the ideal environment for the discovery of the Oxa‐Shono reaction‐Osp2‐Csp3 bond cleavage of esters‐providing two useful products in one‐step: aldehyde selective oxidation level products and a mild de‐esterification method to afford carboxylic acids in the process. The development of the Oxa‐Shono reaction provided the impetus for the discovery of other electrically propelled‐Nsp2‐Csp2 and Nsp2‐Csp3‐bond breaking reactions in bioactive amide and sulfonamide systems. Understanding the voltammetric behaviour of the molecule under study, switching between controlled current‐ or controlled potential‐ electrolysis, and restricting electron flow (the reagent), affords exquisite control over the reaction outcomes in batch and flow. Importantly, this bio‐inspired advance in electrosynthetic dealkylation chemistry mimics the metabolic outcomes observed in nature.

AB - This Personal Account describes the author's groups’ research in the field of electrosynthetic anodic oxidation, beginning with initial trial and error attempts with the Shono oxidation. Early setbacks with complex rotameric amide mixtures, provided the ideal environment for the discovery of the Oxa‐Shono reaction‐Osp2‐Csp3 bond cleavage of esters‐providing two useful products in one‐step: aldehyde selective oxidation level products and a mild de‐esterification method to afford carboxylic acids in the process. The development of the Oxa‐Shono reaction provided the impetus for the discovery of other electrically propelled‐Nsp2‐Csp2 and Nsp2‐Csp3‐bond breaking reactions in bioactive amide and sulfonamide systems. Understanding the voltammetric behaviour of the molecule under study, switching between controlled current‐ or controlled potential‐ electrolysis, and restricting electron flow (the reagent), affords exquisite control over the reaction outcomes in batch and flow. Importantly, this bio‐inspired advance in electrosynthetic dealkylation chemistry mimics the metabolic outcomes observed in nature.

KW - Anodic oxidation

KW - bond cleavage

KW - dealkylation

KW - electrosynthesis

KW - Shono

U2 - 10.1002/tcr.202000116

DO - 10.1002/tcr.202000116

M3 - Article

AN - SCOPUS:85097032951

JO - The Chemical Record

JF - The Chemical Record

SN - 1527-8999

ER -