Concise Synthesis of Isocoumarins through Rh-Catalyzed Direct Vinylene Annulation: Scope and Mechanistic Insight

Mihara, Gen; Ghosh, Koushik; Nishii, Yuji; Miura, Masahiro

doi:https://doi.org/10.1021/acs.orglett.0c02112

Concise Synthesis of Isocoumarins through Rh-Catalyzed Direct Vinylene Annulation: Scope and Mechanistic Insight

Mihara, Gen; Ghosh, Koushik; Nishii, Yuji et al.

Organic Letters, 2020, 22(14), 5706-5711

Number of Access:461（2026-02-18 08:09 Counts）

Identifier to cite or link to this item: https://hdl.handle.net/11094/92814

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Title	Concise Synthesis of Isocoumarins through Rh-Catalyzed Direct Vinylene Annulation: Scope and Mechanistic Insight
Creator	CreatorName Mihara, Gen
	CreatorName Ghosh, Koushik
	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 1000020183626 1000020183626 ORCID 0000-0001-8288-6439 0000-0001-8288-6439 researchmap permalink read0013936 read0013936 Scopus Author ID 7402799909 7402799909 CreatorName Miura, Masahiro
Description	Mihara G., Ghosh K., Nishii Y., et al. Concise Synthesis of Isocoumarins through Rh-Catalyzed Direct Vinylene Annulation: Scope and Mechanistic Insight. Organic Letters. 22(14), 5706-5711, (2020), 17 July 2020; ©2020 American Chemical Society. https://doi.org/10.1021/acs.orglett.0c02112.
Abstract	Transition-metal-catalyzed activation of inert C–H bonds and subsequent C–C bond formation have emerged as pow-erful synthetic tools for the synthesis of elaborate cyclic molecules. In this report, we introduce an efficient synthetic method of 3,4-unsubstituted isocoumarins adopting an electron deficient CpERh complex as the catalyst. The use of vinylene carbonate as a vinylene transfer reagent enables the direct construction of isocoumarins from readily available benzoic acids, without any external oxidants as well as bases. The reaction mechanism is evaluated by computational analysis to find an unprecedented “rhodium shift” event within the catalytic cycle.
Publisher	American Chemical Society
Source Title	Organic Letters
Volume (Issue)	22(14)
Page	5706-5711
Date of Issued	2020-07-17
Language	English
Handle URL	https://hdl.handle.net/11094/92814
PISSN	15237060
eISSN	15237052
Relation.isVersionOf	DOI (Publisher Version) https://doi.org/10.1021/acs.orglett.0c02112
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.0c02112.
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. 2020, 22(14), p. 5706-5711
DC.title	Concise Synthesis of Isocoumarins through Rh-Catalyzed Direct Vinylene Annulation: Scope and Mechanistic Insight
DC.creator	Mihara, Gen
	Ghosh, Koushik
	Nishii, Yuji
	Miura, Masahiro
DC.publisher	American Chemical Society
DC.language' scheme='DCTERMS.RFC1766	English
DC.type' scheme='DCTERMS.DCMIType	Text
DCTERMS.issued' scheme='DCTERMS.W3CDTF	2020-07-17
DC.identifier	https://doi.org/10.1021/acs.orglett.0c02112
DC.description	Mihara G., Ghosh K., Nishii Y., et al. Concise Synthesis of Isocoumarins through Rh-Catalyzed Direct Vinylene Annulation: Scope and Mechanistic Insight. Organic Letters. 22(14), 5706-5711, (2020), 17 July 2020; ©2020 American Chemical Society. https://doi.org/10.1021/acs.orglett.0c02112.
DCTERMS.abstract	Transition-metal-catalyzed activation of inert C–H bonds and subsequent C–C bond formation have emerged as pow-erful synthetic tools for the synthesis of elaborate cyclic molecules. In this report, we introduce an efficient synthetic method of 3,4-unsubstituted isocoumarins adopting an electron deficient CpERh complex as the catalyst. The use of vinylene carbonate as a vinylene transfer reagent enables the direct construction of isocoumarins from readily available benzoic acids, without any external oxidants as well as bases. The reaction mechanism is evaluated by computational analysis to find an unprecedented “rhodium shift” event within the catalytic cycle.
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.0c02112.
DC.format	92814
citation_title	Concise Synthesis of Isocoumarins through Rh-Catalyzed Direct Vinylene Annulation: Scope and Mechanistic Insight
citation_author	Mihara, Gen
	Ghosh, Koushik
	Nishii, Yuji
	Miura, Masahiro
citation_publisher	American Chemical Society
citation_language	English
citation_date	2020-07-17
citation_journal_title	Organic Letters
citation_volume	22
citation_issue	14
citation_firstpage	5706
citation_lastpage	5711
citation_doi	https://doi.org/10.1021/acs.orglett.0c02112
citation_public_url	https://hdl.handle.net/11094/92814

Concise Synthesis of Isocoumarins through Rh-Catalyzed Direct Vinylene Annulation: Scope and Mechanistic Insight

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