Palladium-catalysed C-H arylation of benzophospholes with aryl halides

Xu, Shibo; Nishimura, Kazutoshi; Saito, Kosuke; Hirano, Koji; Miura, Masahiro

doi:https://doi.org/10.1039/d2sc04311d

Palladium-catalysed C-H arylation of benzophospholes with aryl halides

Xu, Shibo; Nishimura, Kazutoshi; Saito, Kosuke et al.

Chemical Science, 2022, 13(36), 10950-10960

Number of Access:474（2025-07-17 21:09 Counts）

Identifier to cite or link to this item: https://hdl.handle.net/11094/92609

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Title	Palladium-catalysed C-H arylation of benzophospholes with aryl halides
Creator	CreatorName Xu, Shibo
	CreatorName Nishimura, Kazutoshi
	CreatorName Saito, Kosuke
	NRID 1000070532696 1000070532696 ORCID 0000-0001-9752-1985 0000-0001-9752-1985 researchmap permalink koj koj Scopus Author ID 7402407063 7402407063 CreatorName Hirano, Koji
	NRID 1000020183626 1000020183626 ORCID 0000-0001-8288-6439 0000-0001-8288-6439 researchmap permalink read0013936 read0013936 Scopus Author ID 7402799909 7402799909 CreatorName Miura, Masahiro
Description	Xu S., Nishimura K., Saito K., et al. Palladium-catalysed C-H arylation of benzophospholes with aryl halides. Chemical Science 13, 10950 (2022); https://doi.org/10.1039/d2sc04311d.
Abstract	A palladium-catalysed C-H arylation of benzophospholes with aryl halides has been developed. The reaction with aryl iodides and bromides proceeds well even under phosphine ligand-free Pd(OAc)2 catalysis whereas the Pd(PCy3)2 is effective for the coupling with less reactive aryl chlorides. The optimal conditions are also applicable to the double arylations with organic dihalides and annulation reaction with ortho-dihalogenated benzenes, making the corresponding benzophosphole-based acceptor-donor-acceptor-type molecules and highly condensed heteroacene-type molecules of potent interest in materials chemistry. Although there are many reports of catalytic C-H functionalisations of related benzoheteroles such as indoles, benzothiophenes, and benzofurans, this is the first successful example of the catalytic direct C-H transformation of benzophospholes, to the best of our knowledge. The preliminary optoelectronic properties of some newly synthesized benzophosphole derivatives are also investigated.
Publisher	Royal Society of Chemistry
Source Title	Chemical Science
Volume (Issue)	13(36)
Page	10950-10960
Date of Issued	2022-08-30
Language	English
Handle URL	https://hdl.handle.net/11094/92609
PISSN	20416520
eISSN	20416539
NCID	AA12555653
Relation.isIdenticalTo	DOI (Publisher Version) https://doi.org/10.1039/d2sc04311d
Access Rights	open access
CopyRight	This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence.
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	Chemical Science. 2022, 13(36), p. 10950-10960
DC.title	Palladium-catalysed C-H arylation of benzophospholes with aryl halides
DC.creator	Xu, Shibo
	Nishimura, Kazutoshi
	Saito, Kosuke
	Hirano, Koji
	Miura, Masahiro
DC.publisher	Royal Society of Chemistry
DC.language' scheme='DCTERMS.RFC1766	English
DC.type' scheme='DCTERMS.DCMIType	Text
DCTERMS.issued' scheme='DCTERMS.W3CDTF	2022-08-30
DC.identifier	https://doi.org/10.1039/d2sc04311d
DC.description	Xu S., Nishimura K., Saito K., et al. Palladium-catalysed C-H arylation of benzophospholes with aryl halides. Chemical Science 13, 10950 (2022); https://doi.org/10.1039/d2sc04311d.
DCTERMS.abstract	A palladium-catalysed C-H arylation of benzophospholes with aryl halides has been developed. The reaction with aryl iodides and bromides proceeds well even under phosphine ligand-free Pd(OAc)2 catalysis whereas the Pd(PCy3)2 is effective for the coupling with less reactive aryl chlorides. The optimal conditions are also applicable to the double arylations with organic dihalides and annulation reaction with ortho-dihalogenated benzenes, making the corresponding benzophosphole-based acceptor-donor-acceptor-type molecules and highly condensed heteroacene-type molecules of potent interest in materials chemistry. Although there are many reports of catalytic C-H functionalisations of related benzoheteroles such as indoles, benzothiophenes, and benzofurans, this is the first successful example of the catalytic direct C-H transformation of benzophospholes, to the best of our knowledge. The preliminary optoelectronic properties of some newly synthesized benzophosphole derivatives are also investigated.
DC.rights	This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence.
DC.format	92609
citation_title	Palladium-catalysed C-H arylation of benzophospholes with aryl halides
citation_author	Xu, Shibo
	Nishimura, Kazutoshi
	Saito, Kosuke
	Hirano, Koji
	Miura, Masahiro
citation_publisher	Royal Society of Chemistry
citation_language	English
citation_date	2022-08-30
citation_journal_title	Chemical Science
citation_volume	13
citation_issue	36
citation_firstpage	10950
citation_lastpage	10960
citation_doi	https://doi.org/10.1039/d2sc04311d
citation_public_url	https://hdl.handle.net/11094/92609

Palladium-catalysed C-H arylation of benzophospholes with aryl halides

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