Electrochemical cascade access to hetero[8]circulenes as potent organophotocatalysts for diverse C–X bond formations

Gabr, Ahmed S.; Salem, Mohamed S.H.; Khalid, Md Imrul; Takahashi, Ryota; Nishimoto, Yoshihiro; Yasuda, Makoto; Takizawa, Shinobu

doi:https://doi.org/10.1038/s41467-025-60889-w

Electrochemical cascade access to hetero[8]circulenes as potent organophotocatalysts for diverse C–X bond formations

Gabr, Ahmed S.; Salem, Mohamed S.H.; Khalid, Md Imrul et al.

Nature Communications, 2025, 16(1), 5682

Number of Access:18（2025-11-27 15:08 Counts）

Identifier to cite or link to this item: https://hdl.handle.net/11094/102916

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Title	Electrochemical cascade access to hetero[8]circulenes as potent organophotocatalysts for diverse C–X bond formations
Creator	CreatorName Gabr, Ahmed S.
	CreatorName Salem, Mohamed S.H.
	CreatorName Khalid, Md Imrul
	CreatorName Takahashi, Ryota
	NRID 1000030550115 1000030550115 ORCID 0000-0002-7182-0503 0000-0002-7182-0503 researchmap permalink nishimoto123 nishimoto123 Scopus Author ID 15048464600 15048464600 CreatorName Nishimoto, Yoshihiro
	NRID 1000040273601 1000040273601 ORCID 0000-0002-6618-2893 0000-0002-6618-2893 researchmap permalink read0185253 read0185253 Scopus Author ID 7402645045 7402645045 CreatorName Yasuda, Makoto
	NRID 1000050324851 1000050324851 ORCID 0000-0002-9668-1888 0000-0002-9668-1888 researchmap permalink read0068650 read0068650 Scopus Author ID 7102334067 7102334067 CreatorName Takizawa, Shinobu
Description	Gabr A.S., Salem M.S.H., Khalid M.I., et al. Electrochemical cascade access to hetero[8]circulenes as potent organophotocatalysts for diverse C–X bond formations. Nature Communications 16, 5682 (2025); https://doi.org/10.1038/s41467-025-60889-w.
Abstract	The chemistry of hetero[8]circulenes has been limited to three main types, constrained by synthetic challenges in creating unsymmetrical variants. Herein, we introduce an electrochemical approach to a type of hetero[8]circulene, featuring five hexagons and three pentagons. Our method capitalizes on the sustainability and selectivity of electrochemistry, utilizing differential oxidation potentials to generate dioxaza[8]circulenes through selective intermolecular and intramolecular couplings under mild conditions, achieving yields of up to 83% with good functional group tolerance. We further refine this process into a one-pot protocol using commercially available substrates, forming six new bonds. Comprehensive structural, optical, and electrochemical characterizations, including X-ray crystallography, spectrophotometric analysis, and DFT calculations, are conducted. Inspired by their distinct structural and redox properties, we explore the application of dioxaza[8]circulenes as organophotocatalysts for diverse C–X (X = C, B, S, P) bond formation achieving up to 97% yields under LED light irradiation (365 nm) without transition metals.
Publisher	Nature Research
Source Title	Nature Communications
Volume (Issue)	16(1)
Page	5682
Date of Issued	2025-07-01
Language	English
Handle URL	https://hdl.handle.net/11094/102916
eISSN	20411723
Relation.isIdenticalTo	DOI (Publisher Version) https://doi.org/10.1038/s41467-025-60889-w
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
DCMI Type	Text
DCTERMS.bibliographicCitation	Nature Communications. 2025, 16(1), p. 5682
DC.title	Electrochemical cascade access to hetero[8]circulenes as potent organophotocatalysts for diverse C–X bond formations
DC.creator	Gabr, Ahmed S.
	Salem, Mohamed S.H.
	Khalid, Md Imrul
	Takahashi, Ryota
	Nishimoto, Yoshihiro
	Yasuda, Makoto
	Takizawa, Shinobu
DC.publisher	Nature Research
DC.language' scheme='DCTERMS.RFC1766	English
DC.type' scheme='DCTERMS.DCMIType	Text
DCTERMS.issued' scheme='DCTERMS.W3CDTF	2025-07-01
DC.identifier	https://doi.org/10.1038/s41467-025-60889-w
DC.description	Gabr A.S., Salem M.S.H., Khalid M.I., et al. Electrochemical cascade access to hetero[8]circulenes as potent organophotocatalysts for diverse C–X bond formations. Nature Communications 16, 5682 (2025); https://doi.org/10.1038/s41467-025-60889-w.
DCTERMS.abstract	The chemistry of hetero[8]circulenes has been limited to three main types, constrained by synthetic challenges in creating unsymmetrical variants. Herein, we introduce an electrochemical approach to a type of hetero[8]circulene, featuring five hexagons and three pentagons. Our method capitalizes on the sustainability and selectivity of electrochemistry, utilizing differential oxidation potentials to generate dioxaza[8]circulenes through selective intermolecular and intramolecular couplings under mild conditions, achieving yields of up to 83% with good functional group tolerance. We further refine this process into a one-pot protocol using commercially available substrates, forming six new bonds. Comprehensive structural, optical, and electrochemical characterizations, including X-ray crystallography, spectrophotometric analysis, and DFT calculations, are conducted. Inspired by their distinct structural and redox properties, we explore the application of dioxaza[8]circulenes as organophotocatalysts for diverse C–X (X = C, B, S, P) bond formation achieving up to 97% yields under LED light irradiation (365 nm) without transition metals.
DC.rights	This article is licensed under a Creative Commons Attribution 4.0 International License.
DC.format	102916
citation_title	Electrochemical cascade access to hetero[8]circulenes as potent organophotocatalysts for diverse C–X bond formations
citation_author	Gabr, Ahmed S.
	Salem, Mohamed S.H.
	Khalid, Md Imrul
	Takahashi, Ryota
	Nishimoto, Yoshihiro
	Yasuda, Makoto
	Takizawa, Shinobu
citation_publisher	Nature Research
citation_language	English
citation_date	2025-07-01
citation_journal_title	Nature Communications
citation_volume	16
citation_issue	1
citation_firstpage	5682
citation_doi	https://doi.org/10.1038/s41467-025-60889-w
citation_public_url	https://hdl.handle.net/11094/102916

Electrochemical cascade access to hetero[8]circulenes as potent organophotocatalysts for diverse C–X bond formations

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