Copper-Catalyzed Electrophilic Amination of gem-Diborylalkanes with Hydroxylamines Providing α-Aminoboronic Acid Derivatives

Nishino, Soshi; Hirano, Koji; Miura, Masahiro

doi:https://doi.org/10.1021/acs.orglett.9b01640

Copper-Catalyzed Electrophilic Amination of gem-Diborylalkanes with Hydroxylamines Providing α-Aminoboronic Acid Derivatives

Nishino, Soshi; Hirano, Koji; Miura, Masahiro

Organic Letters, 2019, 21(12), 4759-4762

アクセス数:366件（2025-08-28 19:39 集計）

固定URL: https://hdl.handle.net/11094/92705

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タイトル	Copper-Catalyzed Electrophilic Amination of gem-Diborylalkanes with Hydroxylamines Providing α-Aminoboronic Acid Derivatives
著者	著者名 Nishino, Soshi
	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
	NRID 1000020183626 1000020183626 ORCID 0000-0001-8288-6439 0000-0001-8288-6439 researchmap permalink read0013936 read0013936 Scopus Author ID 7402799909 7402799909 著者名 Miura, Masahiro
内容	Nishino S., Hirano K., Miura M.. Copper-Catalyzed Electrophilic Amination of gem-Diborylalkanes with Hydroxylamines Providing α-Aminoboronic Acid Derivatives. Organic Letters. 21(12), 4759-4762, (2019), 21 June 2019; © 2019 American Chemical Society. https://doi.org/10.1021/acs.orglett.9b01640.
抄録	A copper-catalyzed electrophilic amination of gem-diborylalkanes with hydroxylamines has been developed. The key to its success is the use of the Me3Si-modified 1,2-bis(diphenylphosphino)benzene ligand. Additionally, the reactivity of neopentylglycol derivatives compared to that of commonly used pinacol-derived ones is found to be higher, particularly in the case of relatively sterically congested substrates. The copper catalysis presented here enables the first successful catalytic carbon-heteroatom bond forming reaction of gem-diborylalkanes to form the corresponding α-aminoboronic acid derivatives, which are of great interest in medicinal and pharmaceutical chemistry.
出版者	American Chemical Societyservice@acs.org
収録物名	Organic Letters
巻(号)	21(12)
ページ	4759-4762
刊行年月	2019-06-21
言語	英語
ハンドルURL	https://hdl.handle.net/11094/92705
PISSN	15237060
eISSN	15237052
関連情報 (isVersionOf)	DOI (出版社版) https://doi.org/10.1021/acs.orglett.9b01640
アクセス権	open access
権利情報	© 2019 American Chemical Society.
権利情報	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.9b01640.
出版タイプ	Accepted Manuscript
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	Organic Letters. 2019, 21(12), p. 4759-4762
DC.title	Copper-Catalyzed Electrophilic Amination of gem-Diborylalkanes with Hydroxylamines Providing α-Aminoboronic Acid Derivatives
DC.creator	Nishino, Soshi
	Hirano, Koji
	Miura, Masahiro
DC.publisher	American Chemical Societyservice@acs.org
DC.language' scheme='DCTERMS.RFC1766	英語
DC.type' scheme='DCTERMS.DCMIType	text
DCTERMS.issued' scheme='DCTERMS.W3CDTF	2019-06-21
DC.identifier	https://doi.org/10.1021/acs.orglett.9b01640
DC.description	Nishino S., Hirano K., Miura M.. Copper-Catalyzed Electrophilic Amination of gem-Diborylalkanes with Hydroxylamines Providing α-Aminoboronic Acid Derivatives. Organic Letters. 21(12), 4759-4762, (2019), 21 June 2019; © 2019 American Chemical Society. https://doi.org/10.1021/acs.orglett.9b01640.
DCTERMS.abstract	A copper-catalyzed electrophilic amination of gem-diborylalkanes with hydroxylamines has been developed. The key to its success is the use of the Me3Si-modified 1,2-bis(diphenylphosphino)benzene ligand. Additionally, the reactivity of neopentylglycol derivatives compared to that of commonly used pinacol-derived ones is found to be higher, particularly in the case of relatively sterically congested substrates. The copper catalysis presented here enables the first successful catalytic carbon-heteroatom bond forming reaction of gem-diborylalkanes to form the corresponding α-aminoboronic acid derivatives, which are of great interest in medicinal and pharmaceutical chemistry.
DC.rights	© 2019 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.9b01640.
DC.format	92705
citation_title	Copper-Catalyzed Electrophilic Amination of gem-Diborylalkanes with Hydroxylamines Providing α-Aminoboronic Acid Derivatives
citation_author	Nishino, Soshi
	Hirano, Koji
	Miura, Masahiro
citation_publisher	American Chemical Societyservice@acs.org
citation_language	英語
citation_date	2019-06-21
citation_journal_title	Organic Letters
citation_volume	21
citation_issue	12
citation_firstpage	4759
citation_lastpage	4762
citation_doi	https://doi.org/10.1021/acs.orglett.9b01640
citation_public_url	https://hdl.handle.net/11094/92705

Copper-Catalyzed Electrophilic Amination of gem-Diborylalkanes with Hydroxylamines Providing α-Aminoboronic Acid Derivatives

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