Pd-catalyzed regioselective C−H alkenylation and alkynylation of allylic alcohols with the assistance of a bidentate phenanthroline auxiliary

Hirano, Koji; Miura, Masahiro; Xu, Shibo

doi:https://doi.org/10.1021/acs.orglett.0c03444

Pd-catalyzed regioselective C−H alkenylation and alkynylation of allylic alcohols with the assistance of a bidentate phenanthroline auxiliary

Hirano, Koji; Miura, Masahiro; Xu, Shibo

Organic Letters, 2020, 22(22), 9059-9064

Number of Access:504（2025-07-17 20:34 Counts）

Identifier to cite or link to this item: https://hdl.handle.net/11094/92699

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Title	Pd-catalyzed regioselective C−H alkenylation and alkynylation of allylic alcohols with the assistance of a bidentate phenanthroline auxiliary
Creator	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
	CreatorName Xu, Shibo
Description	Hirano K., Miura M., Xu S.. Pd-catalyzed regioselective C−H alkenylation and alkynylation of allylic alcohols with the assistance of a bidentate phenanthroline auxiliary. Organic Letters. 22(22), 9059-9064, (2020), 20 November 2020; © 2020 American Chemical Society. https://doi.org/10.1021/acs.orglett.0c03444.
Abstract	A Pd-catalyzed regioselective C−H alkenylation of allylic alcohols with electron-deficient alkenes has been developed. The key to success is the introduction of bidentately coordinating phenanthroline directing group, which enables the otherwise challenging and regioselective C−H activation at the proximal alkenyl C−H bonds over the conceivably competitive allylic C−O bond activation. The same Pd/phenanthroline system is efficient for the C−H alkynylation of allylic alcohols with alkynyl bromides.
Publisher	American Chemical Society
Source Title	Organic Letters
Volume (Issue)	22(22)
Page	9059-9064
Date of Issued	2020-11-20
Language	English
Handle URL	https://hdl.handle.net/11094/92699
PISSN	15237060
eISSN	15237052
Relation.isVersionOf	DOI (Publisher Version) https://doi.org/10.1021/acs.orglett.0c03444
Access Rights	open access
CopyRight	© 2020 American Chemical Society
CopyRight	This document is the unedited Author’s version of a Submitted Work that was subsequently accepted for publication in, Organic Letters, copyright © American Chemical Society after peer review. To access the final edited and published work see https://doi.org/10.1021/acs.orglett.0c03444.
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(22), p. 9059-9064
DC.title	Pd-catalyzed regioselective C−H alkenylation and alkynylation of allylic alcohols with the assistance of a bidentate phenanthroline auxiliary
DC.creator	Hirano, Koji
	Miura, Masahiro
	Xu, Shibo
DC.publisher	American Chemical Society
DC.language' scheme='DCTERMS.RFC1766	English
DC.type' scheme='DCTERMS.DCMIType	Text
DCTERMS.issued' scheme='DCTERMS.W3CDTF	2020-11-20
DC.identifier	https://doi.org/10.1021/acs.orglett.0c03444
DC.description	Hirano K., Miura M., Xu S.. Pd-catalyzed regioselective C−H alkenylation and alkynylation of allylic alcohols with the assistance of a bidentate phenanthroline auxiliary. Organic Letters. 22(22), 9059-9064, (2020), 20 November 2020; © 2020 American Chemical Society. https://doi.org/10.1021/acs.orglett.0c03444.
DCTERMS.abstract	A Pd-catalyzed regioselective C−H alkenylation of allylic alcohols with electron-deficient alkenes has been developed. The key to success is the introduction of bidentately coordinating phenanthroline directing group, which enables the otherwise challenging and regioselective C−H activation at the proximal alkenyl C−H bonds over the conceivably competitive allylic C−O bond activation. The same Pd/phenanthroline system is efficient for the C−H alkynylation of allylic alcohols with alkynyl bromides.
DC.rights	© 2020 American Chemical Society
DC.rights	This document is the unedited Author’s version of a Submitted Work that was subsequently accepted for publication in, Organic Letters, copyright © American Chemical Society after peer review. To access the final edited and published work see https://doi.org/10.1021/acs.orglett.0c03444.
DC.format	92699
citation_title	Pd-catalyzed regioselective C−H alkenylation and alkynylation of allylic alcohols with the assistance of a bidentate phenanthroline auxiliary
citation_author	Hirano, Koji
	Miura, Masahiro
	Xu, Shibo
citation_publisher	American Chemical Society
citation_language	English
citation_date	2020-11-20
citation_journal_title	Organic Letters
citation_volume	22
citation_issue	22
citation_firstpage	9059
citation_lastpage	9064
citation_doi	https://doi.org/10.1021/acs.orglett.0c03444
citation_public_url	https://hdl.handle.net/11094/92699

Pd-catalyzed regioselective C−H alkenylation and alkynylation of allylic alcohols with the assistance of a bidentate phenanthroline auxiliary

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