Electrochemical C(sp³)−H Functionalization Using Acetic Acid as a Hydrogen Atom Transfer Reagent

Morii, Yuma; Watanabe, Taito; Saga, Yutaka; Kambe, Tetsuya; Kondo, Mio; Masaoka, Shigeyuki

doi:https://doi.org/10.1002/celc.202400061

Electrochemical C(sp³)−H Functionalization Using Acetic Acid as a Hydrogen Atom Transfer Reagent

Morii, Yuma; Watanabe, Taito; Saga, Yutaka et al.

ChemElectroChem, 2024, 11, e202400061

Number of Access:753（2025-07-27 16:23 Counts）

Identifier to cite or link to this item: https://hdl.handle.net/11094/97092

Link to primary information

File	Format	Terms of use	Size	Views	Date.Available	Description	information
ChemElectroChem_11_e202400061	pdf	None	822 KB	89	2024.07.04

Creative Commons : Attribution

Item Information

Output File Export EndNote Basic Export Mendeley

Title	Electrochemical C(sp³)−H Functionalization Using Acetic Acid as a Hydrogen Atom Transfer Reagent
Creator	CreatorName Morii, Yuma
	CreatorName Watanabe, Taito
	NRID 1000020785521 1000020785521 researchmap permalink ysagagerrard ysagagerrard Scopus Author ID 36515397900 36515397900 CreatorName Saga, Yutaka
	NRID 1000000733495 1000000733495 researchmap permalink kambe kambe Scopus Author ID 36131584400 36131584400 ORCID 0000-0002-9216-2693 0000-0002-9216-2693 CreatorName Kambe, Tetsuya
	NRID 1000020619168 1000020619168 CreatorName Kondo, Mio
	NRID 1000020404048 1000020404048 ORCID 0000-0003-2678-2269 0000-0003-2678-2269 researchmap permalink Shigeyuki_Masaoka Shigeyuki_Masaoka Scopus Author ID 7003310045 7003310045 CreatorName Masaoka, Shigeyuki
Subject	Acetic acid
	C(sp³)−H functionalization
	Electrochemistry
	Hydrogen atom transfer
	Kolbe electrolysis
Description	Morii Y., Watanabe T., Saga Y., et al. Electrochemical C(sp³)−H Functionalization Using Acetic Acid as a Hydrogen Atom Transfer Reagent. ChemElectroChem 11, e202400061 (2024); https://doi.org/https://doi.org/10.1002/celc.202400061.
Abstract	In this study, we developed a novel electrochemical protocol that enables the functionalization of inherently inert C(sp³)−H bonds. In this protocol, one-electron oxidation of acetic acid was used to successfully generate methyl radical, which cleaves the benzylic C(sp³)−H bonds of the substrates via a hydrogen atom transfer (HAT) process, and further reaction with the formed species yields the targeted C(sp³)−H functionalized products. To the best of our knowledge, this is the first example of the use of acetic acid in a HAT process. Notably the reaction has environment-friendly and fine atom economy nature: the reaction is driven by the electrochemical conditions in the absence of expensive or hazardous reagents, producing only gaseous small molecules, hydrogen, carbon dioxide, and methane, as side products.
Publisher	John Wiley and Sons Inc
Source Title	ChemElectroChem
Volume (Issue)	11
Page	e202400061
Date of Issued	2024-05-17
Language	English
Handle URL	https://hdl.handle.net/11094/97092
eISSN	21960216
Relation.isIdenticalTo	DOI (Publisher Version) https://doi.org/10.1002/celc.202400061
Access Rights	open access
CopyRight	This article is licensed under a Creative Commons Attribution 4.0 International License.
oaire:version	Version of Record
Category	学術雑誌論文 Journal Article

Resource Type	journal article
Local Type	Journal Article
DCTERMS.bibliographicCitation	ChemElectroChem. 2024, 11, p. e202400061
DC.title	Electrochemical C(sp³)−H Functionalization Using Acetic Acid as a Hydrogen Atom Transfer Reagent
DC.creator	Morii, Yuma
	Watanabe, Taito
	Saga, Yutaka
	Kambe, Tetsuya
	Kondo, Mio
	Masaoka, Shigeyuki
DC.publisher	John Wiley and Sons Inc
DC.language' scheme='DCTERMS.RFC1766	English
DCTERMS.issued' scheme='DCTERMS.W3CDTF	2024-05-17
DC.identifier	https://doi.org/10.1002/celc.202400061
DC.subject	Acetic acid
	C(sp³)−H functionalization
	Electrochemistry
	Hydrogen atom transfer
	Kolbe electrolysis
DC.description	Morii Y., Watanabe T., Saga Y., et al. Electrochemical C(sp³)−H Functionalization Using Acetic Acid as a Hydrogen Atom Transfer Reagent. ChemElectroChem 11, e202400061 (2024); https://doi.org/https://doi.org/10.1002/celc.202400061.
DCTERMS.abstract	In this study, we developed a novel electrochemical protocol that enables the functionalization of inherently inert C(sp³)−H bonds. In this protocol, one-electron oxidation of acetic acid was used to successfully generate methyl radical, which cleaves the benzylic C(sp³)−H bonds of the substrates via a hydrogen atom transfer (HAT) process, and further reaction with the formed species yields the targeted C(sp³)−H functionalized products. To the best of our knowledge, this is the first example of the use of acetic acid in a HAT process. Notably the reaction has environment-friendly and fine atom economy nature: the reaction is driven by the electrochemical conditions in the absence of expensive or hazardous reagents, producing only gaseous small molecules, hydrogen, carbon dioxide, and methane, as side products.
DC.rights	This article is licensed under a Creative Commons Attribution 4.0 International License.
DC.format	97092
citation_title	Electrochemical C(sp³)−H Functionalization Using Acetic Acid as a Hydrogen Atom Transfer Reagent
citation_author	Morii, Yuma
	Watanabe, Taito
	Saga, Yutaka
	Kambe, Tetsuya
	Kondo, Mio
	Masaoka, Shigeyuki
citation_publisher	John Wiley and Sons Inc
citation_language	English
citation_date	2024-05-17
citation_journal_title	ChemElectroChem
citation_volume	11
citation_firstpage	e202400061
citation_doi	https://doi.org/10.1002/celc.202400061
citation_public_url	https://hdl.handle.net/11094/97092

Electrochemical C(sp³)−H Functionalization Using Acetic Acid as a Hydrogen Atom Transfer Reagent

Link to primary information

Item Information

Show details