Asymmetric Construction of a SeCF₃-Substituted Stereocenter by CuH-Catalyzed Hydroboration of 1-SeCF₃-Alkenes

Matsui, Haruka; Kojima, Yuki; Yasui, Kosuke; Nishii, Yuji; Hirano, Koji

doi:https://doi.org/10.1021/acs.orglett.5c00330

Asymmetric Construction of a SeCF₃-Substituted Stereocenter by CuH-Catalyzed Hydroboration of 1-SeCF₃-Alkenes

Matsui, Haruka; Kojima, Yuki; Yasui, Kosuke et al.

Organic Letters, 2025, 27(8), 2005-2010

Number of Access:49（2025-07-17 21:03 Counts）

Identifier to cite or link to this item: https://hdl.handle.net/11094/101971

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Title	Asymmetric Construction of a SeCF₃-Substituted Stereocenter by CuH-Catalyzed Hydroboration of 1-SeCF₃-Alkenes
Creator	CreatorName Matsui, Haruka
	ORCID 0009-0000-4796-1536 0009-0000-4796-1536 researchmap permalink yuki_kojima yuki_kojima Scopus Author ID 57218704471 57218704471 CreatorName Kojima, Yuki
	NRID 1000010877640 1000010877640 ORCID 0000-0002-3906-8307 0000-0002-3906-8307 researchmap permalink k_yasui k_yasui CreatorName Yasui, Kosuke
	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
Abstract	A copper hydride (CuH)-catalyzed regio- and enantioselective hydroboration of 1-trifluoromethylseleno (SeCF₃)-alkenes with H-Bpin has been developed. The regio- and enantioselective hydrocupration of an in situ generated CuH species is followed by a boration reaction to successfully construct a SeCF₃- and Bpin-substituted chiral carbon center. The key to success is the appropriate choice of tBu-modified biphosphine ligands, which enables an overwhelming high reaction efficiency.
Publisher	American Chemical Society
Source Title	Organic Letters
Volume (Issue)	27(8)
Page	2005-2010
Date of Issued	2025-02-20
Language	English
Handle URL	https://hdl.handle.net/11094/101971
PISSN	15237060
eISSN	15237052
Relation.isVersionOf	DOI (Publisher Version) https://doi.org/10.1021/acs.orglett.5c00330
Access Rights	embargoed 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.5c00330.
CopyRight	The full-text file will be made open to the public on 20 February 2026 in accordance with the publisher's policy.
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. 2025, 27(8), p. 2005-2010
DC.title	Asymmetric Construction of a SeCF₃-Substituted Stereocenter by CuH-Catalyzed Hydroboration of 1-SeCF₃-Alkenes
DC.creator	Matsui, Haruka
	Kojima, Yuki
	Yasui, Kosuke
	Nishii, Yuji
	Hirano, Koji
DC.publisher	American Chemical Society
DC.language' scheme='DCTERMS.RFC1766	English
DC.type' scheme='DCTERMS.DCMIType	Text
DCTERMS.issued' scheme='DCTERMS.W3CDTF	2025-02-20
DC.identifier	https://doi.org/10.1021/acs.orglett.5c00330
DCTERMS.abstract	A copper hydride (CuH)-catalyzed regio- and enantioselective hydroboration of 1-trifluoromethylseleno (SeCF₃)-alkenes with H-Bpin has been developed. The regio- and enantioselective hydrocupration of an in situ generated CuH species is followed by a boration reaction to successfully construct a SeCF₃- and Bpin-substituted chiral carbon center. The key to success is the appropriate choice of tBu-modified biphosphine ligands, which enables an overwhelming high reaction efficiency.
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.5c00330.
DC.rights	The full-text file will be made open to the public on 20 February 2026 in accordance with the publisher's policy.
DC.format	101971
citation_title	Asymmetric Construction of a SeCF₃-Substituted Stereocenter by CuH-Catalyzed Hydroboration of 1-SeCF₃-Alkenes
citation_author	Matsui, Haruka
	Kojima, Yuki
	Yasui, Kosuke
	Nishii, Yuji
	Hirano, Koji
citation_publisher	American Chemical Society
citation_language	English
citation_date	2025-02-20
citation_journal_title	Organic Letters
citation_volume	27
citation_issue	8
citation_firstpage	2005
citation_lastpage	2010
citation_doi	https://doi.org/10.1021/acs.orglett.5c00330
citation_public_url	https://hdl.handle.net/11094/101971

Asymmetric Construction of a SeCF₃-Substituted Stereocenter by CuH-Catalyzed Hydroboration of 1-SeCF₃-Alkenes

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