Asymmetric Synthesis of SCF₃₋Substituted Alkylboronates by Copper-Catalyzed Hydroboration of 1-Trifluoromethylthioalkenes

Kojima, Yuki; Nishii, Yuji; Hirano, Koji

doi:https://doi.org/10.1002/anie.202403337

Asymmetric Synthesis of SCF₃₋Substituted Alkylboronates by Copper-Catalyzed Hydroboration of 1-Trifluoromethylthioalkenes

Kojima, Yuki; Nishii, Yuji; Hirano, Koji

Angewandte Chemie - International Edition, 2024, 63(24), e202403337

アクセス数:203件（2025-10-23 20:31 集計）

固定URL: https://hdl.handle.net/11094/95747

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タイトル	Asymmetric Synthesis of SCF₃₋Substituted Alkylboronates by Copper-Catalyzed Hydroboration of 1-Trifluoromethylthioalkenes
著者	著者名 Kojima, Yuki
	NRID 1000070773787 1000070773787 ORCID 0000-0002-6824-0639 0000-0002-6824-0639 researchmap permalink y_nishii y_nishii Scopus Author ID 55233363700 55233363700 著者名 Nishii, Yuji
	NRID 1000070532696 1000070532696 ORCID 0000-0001-9752-1985 0000-0001-9752-1985 researchmap permalink koj koj Scopus Author ID 7402407063 7402407063 著者名 Hirano, Koji
キーワード等	asymmetric catalysis
	copper
	fluorine molecule
	hydrofunctionalization
	trifluoromethylthio group
内容	Kojima Y., Nishii Y., Hirano K.. Asymmetric Synthesis of SCF₃₋Substituted Alkylboronates by Copper-Catalyzed Hydroboration of 1-Trifluoromethylthioalkenes. Angewandte Chemie - International Edition , (2024); https://doi.org/10.1002/anie.202403337.
抄録	A synthetic method for preparation of optically active trifluoromethylthio (SCF₃) compounds by a copper-catalyzed regio- and enantioselective hydroboration of 1-trifluoromethylthioalkenes with H-Bpin has been developed. The enantioselective hydrocupration of an in situ generated CuH species and subsequent boration reaction generate a chiral SCF₃₋containing alkylboronate, of which Bpin moiety can be further transformed to deliver various optically active SCF₃ molecules. Computational studies suggest that the SCF₃ group successfully controls the regioselectivity in the reaction.
出版者	John Wiley and Sons Inc
収録物名	Angewandte Chemie - International Edition
巻(号)	63(24)
ページ	e202403337
刊行年月	2024-05-10
言語	英語
ハンドルURL	https://hdl.handle.net/11094/95747
PISSN	14337851
eISSN	15213773
関連情報 (isIdenticalTo)	DOI (出版社版) https://doi.org/10.1002/anie.202403337
アクセス権	open access
権利情報	This article is licensed under a Creative Commons Attribution 4.0 International License.
出版タイプ	Version of Record
カテゴリ	学術雑誌論文 Journal Article

資源タイプ	学術雑誌論文
ローカル資源タイプ	学術雑誌論文
DCMI資源タイプ	text
DCTERMS.bibliographicCitation	Angewandte Chemie - International Edition. 2024, 63(24), p. e202403337
DC.title	Asymmetric Synthesis of SCF₃₋Substituted Alkylboronates by Copper-Catalyzed Hydroboration of 1-Trifluoromethylthioalkenes
DC.creator	Kojima, Yuki
	Nishii, Yuji
	Hirano, Koji
DC.publisher	John Wiley and Sons Inc
DC.language' scheme='DCTERMS.RFC1766	英語
DC.type' scheme='DCTERMS.DCMIType	text
DCTERMS.issued' scheme='DCTERMS.W3CDTF	2024-05-10
DC.identifier	https://doi.org/10.1002/anie.202403337
DC.subject	asymmetric catalysis
	copper
	fluorine molecule
	hydrofunctionalization
	trifluoromethylthio group
DC.description	Kojima Y., Nishii Y., Hirano K.. Asymmetric Synthesis of SCF₃₋Substituted Alkylboronates by Copper-Catalyzed Hydroboration of 1-Trifluoromethylthioalkenes. Angewandte Chemie - International Edition , (2024); https://doi.org/10.1002/anie.202403337.
DCTERMS.abstract	A synthetic method for preparation of optically active trifluoromethylthio (SCF₃) compounds by a copper-catalyzed regio- and enantioselective hydroboration of 1-trifluoromethylthioalkenes with H-Bpin has been developed. The enantioselective hydrocupration of an in situ generated CuH species and subsequent boration reaction generate a chiral SCF₃₋containing alkylboronate, of which Bpin moiety can be further transformed to deliver various optically active SCF₃ molecules. Computational studies suggest that the SCF₃ group successfully controls the regioselectivity in the reaction.
DC.rights	This article is licensed under a Creative Commons Attribution 4.0 International License.
DC.format	95747
citation_title	Asymmetric Synthesis of SCF₃₋Substituted Alkylboronates by Copper-Catalyzed Hydroboration of 1-Trifluoromethylthioalkenes
citation_author	Kojima, Yuki
	Nishii, Yuji
	Hirano, Koji
citation_publisher	John Wiley and Sons Inc
citation_language	英語
citation_date	2024-05-10
citation_journal_title	Angewandte Chemie - International Edition
citation_volume	63
citation_issue	24
citation_firstpage	e202403337
citation_doi	https://doi.org/10.1002/anie.202403337
citation_public_url	https://hdl.handle.net/11094/95747

Asymmetric Synthesis of SCF₃₋Substituted Alkylboronates by Copper-Catalyzed Hydroboration of 1-Trifluoromethylthioalkenes

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