Selective Synthesis of C4-Functionalized Benzofurans by Rhodium-Catalyzed Vinylene Transfer: Computational Study on the Cyclopentadienyl Ligand

Kitano, Junya; Nishii, Yuji; Miura, Masahiro

doi:https://doi.org/10.1021/acs.orglett.2c02030

Selective Synthesis of C4-Functionalized Benzofurans by Rhodium-Catalyzed Vinylene Transfer: Computational Study on the Cyclopentadienyl Ligand

Kitano, Junya; Nishii, Yuji; Miura, Masahiro

Organic Letters, 2022, 24(31), 5679-5683

Number of Access:281（2025-08-14 07:22 Counts）

Identifier to cite or link to this item: https://hdl.handle.net/11094/92807

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Title	Selective Synthesis of C4-Functionalized Benzofurans by Rhodium-Catalyzed Vinylene Transfer: Computational Study on the Cyclopentadienyl Ligand
Creator	CreatorName Kitano, Junya
	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	Kitano J., Nishii Y., Miura M.. Selective Synthesis of C4-Functionalized Benzofurans by Rhodium-Catalyzed Vinylene Transfer: Computational Study on the Cyclopentadienyl Ligand. Organic Letters. 24(31), 5679-5683, (2022), 12 August 2022; ©2022 American Chemical Society. https://doi.org/10.1021/acs.orglett.2c02030.
Abstract	Benzofuran is a privileged structure in many bioactive compounds; however, the controlled synthesis of C2,C3-non-substituted benzofurans has been scares. In particular, cumbersome multistep processes are inevitable for the most inaccessible C4-substituted isomers. Herein, we report a Rh-catalyzed direct vinylene annulation of readily available m-salicylic acid derivatives with vinylene carbonate to achieve selective construction of C4-substituted benzofurans. The Weinreb amide directing group facilitated the following product derivatization. The reaction mechanism was investigated by DFT calculations.
Publisher	American Chemical Society
Source Title	Organic Letters
Volume (Issue)	24(31)
Page	5679-5683
Date of Issued	2022-08-12
Language	English
Handle URL	https://hdl.handle.net/11094/92807
PISSN	15237060
eISSN	15237052
NCID	AA11347843
Relation.isVersionOf	DOI (Publisher Version) https://doi.org/10.1021/acs.orglett.2c02030
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.2c02030.
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. 2022, 24(31), p. 5679-5683
DC.title	Selective Synthesis of C4-Functionalized Benzofurans by Rhodium-Catalyzed Vinylene Transfer: Computational Study on the Cyclopentadienyl Ligand
DC.creator	Kitano, Junya
	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	2022-08-12
DC.identifier	https://doi.org/10.1021/acs.orglett.2c02030
DC.description	Kitano J., Nishii Y., Miura M.. Selective Synthesis of C4-Functionalized Benzofurans by Rhodium-Catalyzed Vinylene Transfer: Computational Study on the Cyclopentadienyl Ligand. Organic Letters. 24(31), 5679-5683, (2022), 12 August 2022; ©2022 American Chemical Society. https://doi.org/10.1021/acs.orglett.2c02030.
DCTERMS.abstract	Benzofuran is a privileged structure in many bioactive compounds; however, the controlled synthesis of C2,C3-non-substituted benzofurans has been scares. In particular, cumbersome multistep processes are inevitable for the most inaccessible C4-substituted isomers. Herein, we report a Rh-catalyzed direct vinylene annulation of readily available m-salicylic acid derivatives with vinylene carbonate to achieve selective construction of C4-substituted benzofurans. The Weinreb amide directing group facilitated the following product derivatization. The reaction mechanism was investigated by DFT calculations.
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.2c02030.
DC.format	92807
citation_title	Selective Synthesis of C4-Functionalized Benzofurans by Rhodium-Catalyzed Vinylene Transfer: Computational Study on the Cyclopentadienyl Ligand
citation_author	Kitano, Junya
	Nishii, Yuji
	Miura, Masahiro
citation_publisher	American Chemical Society
citation_language	English
citation_date	2022-08-12
citation_journal_title	Organic Letters
citation_volume	24
citation_issue	31
citation_firstpage	5679
citation_lastpage	5683
citation_doi	https://doi.org/10.1021/acs.orglett.2c02030
citation_public_url	https://hdl.handle.net/11094/92807

Selective Synthesis of C4-Functionalized Benzofurans by Rhodium-Catalyzed Vinylene Transfer: Computational Study on the Cyclopentadienyl Ligand

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