Hydroamination, Aminoboration, and Carboamination with Electrophilic Amination Reagents: Umpolung-Enabled Regio- and Stereoselective Synthesis of N-Containing Molecules from Alkenes and Alkynes

Hirano, Koji; Miura, Masahiro

doi:https://doi.org/10.1021/jacs.1c12663

Hydroamination, Aminoboration, and Carboamination with Electrophilic Amination Reagents: Umpolung-Enabled Regio- and Stereoselective Synthesis of N-Containing Molecules from Alkenes and Alkynes

Hirano, Koji; Miura, Masahiro

Journal of the American Chemical Society, 2022, 144(2), 648-661

Number of Access:530（2025-07-17 20:12 Counts）

Identifier to cite or link to this item: https://hdl.handle.net/11094/92694

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Title	Hydroamination, Aminoboration, and Carboamination with Electrophilic Amination Reagents: Umpolung-Enabled Regio- and Stereoselective Synthesis of N-Containing Molecules from Alkenes and Alkynes
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
Creator	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	Hirano K., Miura M.. Hydroamination, Aminoboration, and Carboamination with Electrophilic Amination Reagents: Umpolung-Enabled Regio- and Stereoselective Synthesis of N-Containing Molecules from Alkenes and Alkynes. Journal of the American Chemical Society. 144(2), 648-661, (2022), 19 January 2022; © 2022 American Chemical Society. https://doi.org/10.1021/jacs.1c12663.
Abstract	Nitrogen (N) is ubiquitously found in bioactive molecules, pharmaceutical agents, and organic functional materials. Accordingly, development of new C–N bond-forming catalysis has been one of the long-standing research subjects in synthetic organic chemistry. In this Perspective, recent advances in highly selective amination reactions with electrophilic amination reagents are described: by taking advantage of the concept of nitrogen umpolung, otherwise challenging aminofunctionalizations, such as hydroamination, aminoboration, and carboamination, of readily available feedstock-like alkenes and alkynes are possible, giving densely functionalized complex and often chiral alkylamines with high selectivity. The scope, limitations, and reaction mechanism are briefly summarized.
Publisher	American Chemical Society
Source Title	Journal of the American Chemical Society
Volume (Issue)	144(2)
Page	648-661
Date of Issued	2022-01-19
Language	English
Handle URL	https://hdl.handle.net/11094/92694
PISSN	00027863
eISSN	15205126
Relation.isVersionOf	DOI (Publisher Version) https://doi.org/10.1021/jacs.1c12663
Access Rights	open access
CopyRight	© 2022 American Chemical Society
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	Journal of the American Chemical Society. 2022, 144(2), p. 648-661
DC.title	Hydroamination, Aminoboration, and Carboamination with Electrophilic Amination Reagents: Umpolung-Enabled Regio- and Stereoselective Synthesis of N-Containing Molecules from Alkenes and Alkynes
DC.creator	Hirano, Koji
DC.creator	Miura, Masahiro
DC.publisher	American Chemical Society
DC.language' scheme='DCTERMS.RFC1766	English
DC.type' scheme='DCTERMS.DCMIType	Text
DCTERMS.issued' scheme='DCTERMS.W3CDTF	2022-01-19
DC.identifier	https://doi.org/10.1021/jacs.1c12663
DC.description	Hirano K., Miura M.. Hydroamination, Aminoboration, and Carboamination with Electrophilic Amination Reagents: Umpolung-Enabled Regio- and Stereoselective Synthesis of N-Containing Molecules from Alkenes and Alkynes. Journal of the American Chemical Society. 144(2), 648-661, (2022), 19 January 2022; © 2022 American Chemical Society. https://doi.org/10.1021/jacs.1c12663.
DCTERMS.abstract	Nitrogen (N) is ubiquitously found in bioactive molecules, pharmaceutical agents, and organic functional materials. Accordingly, development of new C–N bond-forming catalysis has been one of the long-standing research subjects in synthetic organic chemistry. In this Perspective, recent advances in highly selective amination reactions with electrophilic amination reagents are described: by taking advantage of the concept of nitrogen umpolung, otherwise challenging aminofunctionalizations, such as hydroamination, aminoboration, and carboamination, of readily available feedstock-like alkenes and alkynes are possible, giving densely functionalized complex and often chiral alkylamines with high selectivity. The scope, limitations, and reaction mechanism are briefly summarized.
DC.rights	© 2022 American Chemical Society
DC.format	92694
citation_title	Hydroamination, Aminoboration, and Carboamination with Electrophilic Amination Reagents: Umpolung-Enabled Regio- and Stereoselective Synthesis of N-Containing Molecules from Alkenes and Alkynes
citation_author	Hirano, Koji
citation_author	Miura, Masahiro
citation_publisher	American Chemical Society
citation_language	English
citation_date	2022-01-19
citation_journal_title	Journal of the American Chemical Society
citation_volume	144
citation_issue	2
citation_firstpage	648
citation_lastpage	661
citation_doi	https://doi.org/10.1021/jacs.1c12663
citation_public_url	https://hdl.handle.net/11094/92694

Hydroamination, Aminoboration, and Carboamination with Electrophilic Amination Reagents: Umpolung-Enabled Regio- and Stereoselective Synthesis of N-Containing Molecules from Alkenes and Alkynes

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