Rhodium-Catalyzed Isoquinoline Synthesis Using Vinyl Selenone as Oxidizing Acetylene Surrogate

Inami, Ayumi; Nishii, Yuji; Hirano, Koji; Miura, Masahiro

doi:https://doi.org/10.1021/acs.orglett.3c00826

Rhodium-Catalyzed Isoquinoline Synthesis Using Vinyl Selenone as Oxidizing Acetylene Surrogate

Inami, Ayumi; Nishii, Yuji; Hirano, Koji et al.

Organic Letters, 2023, 25(18), 3206-3209

Number of Access:173（2025-07-17 20:36 Counts）

Identifier to cite or link to this item: https://hdl.handle.net/11094/94008

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Title	Rhodium-Catalyzed Isoquinoline Synthesis Using Vinyl Selenone as Oxidizing Acetylene Surrogate
Creator	CreatorName Inami, Ayumi
	NRID 1000070773787 1000070773787 ORCID 0000-0002-6824-0639 0000-0002-6824-0639 researchmap permalink y_nishii y_nishii Scopus Author ID 55233363700 55233363700 CreatorName Nishii, Yuji
	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	Inami A., Nishii Y., Hirano K., et al. Rhodium-Catalyzed Isoquinoline Synthesis Using Vinyl Selenone as Oxidizing Acetylene Surrogate. Organic Letters 25, 3206 (2023); https://doi.org/10.1021/acs.orglett.3c00826.
Abstract	Isoquinoline is a privileged structure in many bioactive compounds and valuable ligands. Transition-metal-catalyzed oxidative annulation of imine derivatives has become a promising synthetic method; however, catalytic synthesis of 3,4-nonsubstituted isoquinolines by formal acetylene annulation has been scarce to date. Herein, we introduce vinyl selenone as an effective acetylene surrogate for the Rh-catalyzed annulative coupling under mild conditions. The Se fragment can be recovered as diselenide and recycled. The product can readily be converted to 1-aminoisoquinolines.
Publisher	American Chemical Society
Source Title	Organic Letters
Volume (Issue)	25(18)
Page	3206-3209
Date of Issued	2023-05-12
Language	English
Handle URL	https://hdl.handle.net/11094/94008
PISSN	15237060
eISSN	15237052
Relation.isVersionOf	DOI (Publisher Version) https://doi.org/10.1021/acs.orglett.3c00826
Access Rights	open access
CopyRight	This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.orglett.3c00826.
oaire:version	Accepted Manuscript
Category	学術雑誌論文 Journal Article

Resource Type	journal article
Local Type	Journal Article
DCMI Type	Text
DCTERMS.bibliographicCitation	Organic Letters. 2023, 25(18), p. 3206-3209
DC.title	Rhodium-Catalyzed Isoquinoline Synthesis Using Vinyl Selenone as Oxidizing Acetylene Surrogate
DC.creator	Inami, Ayumi
	Nishii, Yuji
	Hirano, Koji
	Miura, Masahiro
DC.publisher	American Chemical Society
DC.language' scheme='DCTERMS.RFC1766	English
DC.type' scheme='DCTERMS.DCMIType	Text
DCTERMS.issued' scheme='DCTERMS.W3CDTF	2023-05-12
DC.identifier	https://doi.org/10.1021/acs.orglett.3c00826
DC.description	Inami A., Nishii Y., Hirano K., et al. Rhodium-Catalyzed Isoquinoline Synthesis Using Vinyl Selenone as Oxidizing Acetylene Surrogate. Organic Letters 25, 3206 (2023); https://doi.org/10.1021/acs.orglett.3c00826.
DCTERMS.abstract	Isoquinoline is a privileged structure in many bioactive compounds and valuable ligands. Transition-metal-catalyzed oxidative annulation of imine derivatives has become a promising synthetic method; however, catalytic synthesis of 3,4-nonsubstituted isoquinolines by formal acetylene annulation has been scarce to date. Herein, we introduce vinyl selenone as an effective acetylene surrogate for the Rh-catalyzed annulative coupling under mild conditions. The Se fragment can be recovered as diselenide and recycled. The product can readily be converted to 1-aminoisoquinolines.
DC.rights	This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.orglett.3c00826.
DC.format	94008
citation_title	Rhodium-Catalyzed Isoquinoline Synthesis Using Vinyl Selenone as Oxidizing Acetylene Surrogate
citation_author	Inami, Ayumi
	Nishii, Yuji
	Hirano, Koji
	Miura, Masahiro
citation_publisher	American Chemical Society
citation_language	English
citation_date	2023-05-12
citation_journal_title	Organic Letters
citation_volume	25
citation_issue	18
citation_firstpage	3206
citation_lastpage	3209
citation_doi	https://doi.org/10.1021/acs.orglett.3c00826
citation_public_url	https://hdl.handle.net/11094/94008

Rhodium-Catalyzed Isoquinoline Synthesis Using Vinyl Selenone as Oxidizing Acetylene Surrogate

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