N-Alkylation of functionalized amines with alcohols using a copper–gold mixed photocatalytic system

Abstract Direct functionalization of amino groups in complex organic molecules is one of the most important key technologies in modern organic synthesis, especially in the synthesis of bio-active chemicals and pharmaceuticals. Whereas numerous chemical reactions of amines have been developed to date...

Descripción completa

Guardado en:

Detalles Bibliográficos
Autores principales:	Lyu-Ming Wang, Yuna Morioka, Kellie Jenkinson, Andrew E. H. Wheatley, Susumu Saito, Hiroshi Naka
Formato:	article
Lenguaje:	EN
Publicado:	Nature Portfolio 2018
Materias:	Medicine R Science Q
Acceso en línea:	https://doaj.org/article/179fd25fa50e43bda5b9019a5fc1ae24
Etiquetas:	Agregar Etiqueta Sin Etiquetas, Sea el primero en etiquetar este registro!

id	oai:doaj.org-article:179fd25fa50e43bda5b9019a5fc1ae24
record_format	dspace
spelling	oai:doaj.org-article:179fd25fa50e43bda5b9019a5fc1ae242021-12-02T15:08:56ZN-Alkylation of functionalized amines with alcohols using a copper–gold mixed photocatalytic system10.1038/s41598-018-25293-z2045-2322https://doaj.org/article/179fd25fa50e43bda5b9019a5fc1ae242018-05-01T00:00:00Zhttps://doi.org/10.1038/s41598-018-25293-zhttps://doaj.org/toc/2045-2322Abstract Direct functionalization of amino groups in complex organic molecules is one of the most important key technologies in modern organic synthesis, especially in the synthesis of bio-active chemicals and pharmaceuticals. Whereas numerous chemical reactions of amines have been developed to date, a selective, practical method for functionalizing complex amines is still highly demanded. Here we report the first late-stage N-alkylation of pharmaceutically relevant amines with alcohols at ambient temperature. This reaction was achieved by devising a mixed heterogeneous photocatalyst in situ prepared from Cu/TiO2 and Au/TiO2. The mixed photocatalytic system enabled the rapid N-alkylation of pharmaceutically relevant molecules, the selective mono- and di-alkylation of primary amines, and the non-symmetrical dialkylation of primary amines to hetero-substituted tertiary amines.Lyu-Ming WangYuna MoriokaKellie JenkinsonAndrew E. H. WheatleySusumu SaitoHiroshi NakaNature PortfolioarticleMedicineRScienceQENScientific Reports, Vol 8, Iss 1, Pp 1-7 (2018)
institution	DOAJ
collection	DOAJ
language	EN
topic	Medicine R Science Q
spellingShingle	Medicine R Science Q Lyu-Ming Wang Yuna Morioka Kellie Jenkinson Andrew E. H. Wheatley Susumu Saito Hiroshi Naka N-Alkylation of functionalized amines with alcohols using a copper–gold mixed photocatalytic system
description	Abstract Direct functionalization of amino groups in complex organic molecules is one of the most important key technologies in modern organic synthesis, especially in the synthesis of bio-active chemicals and pharmaceuticals. Whereas numerous chemical reactions of amines have been developed to date, a selective, practical method for functionalizing complex amines is still highly demanded. Here we report the first late-stage N-alkylation of pharmaceutically relevant amines with alcohols at ambient temperature. This reaction was achieved by devising a mixed heterogeneous photocatalyst in situ prepared from Cu/TiO2 and Au/TiO2. The mixed photocatalytic system enabled the rapid N-alkylation of pharmaceutically relevant molecules, the selective mono- and di-alkylation of primary amines, and the non-symmetrical dialkylation of primary amines to hetero-substituted tertiary amines.
format	article
author	Lyu-Ming Wang Yuna Morioka Kellie Jenkinson Andrew E. H. Wheatley Susumu Saito Hiroshi Naka
author_facet	Lyu-Ming Wang Yuna Morioka Kellie Jenkinson Andrew E. H. Wheatley Susumu Saito Hiroshi Naka
author_sort	Lyu-Ming Wang
title	N-Alkylation of functionalized amines with alcohols using a copper–gold mixed photocatalytic system
title_short	N-Alkylation of functionalized amines with alcohols using a copper–gold mixed photocatalytic system
title_full	N-Alkylation of functionalized amines with alcohols using a copper–gold mixed photocatalytic system
title_fullStr	N-Alkylation of functionalized amines with alcohols using a copper–gold mixed photocatalytic system
title_full_unstemmed	N-Alkylation of functionalized amines with alcohols using a copper–gold mixed photocatalytic system
title_sort	n-alkylation of functionalized amines with alcohols using a copper–gold mixed photocatalytic system
publisher	Nature Portfolio
publishDate	2018
url	https://doaj.org/article/179fd25fa50e43bda5b9019a5fc1ae24
work_keys_str_mv	AT lyumingwang nalkylationoffunctionalizedamineswithalcoholsusingacoppergoldmixedphotocatalyticsystem AT yunamorioka nalkylationoffunctionalizedamineswithalcoholsusingacoppergoldmixedphotocatalyticsystem AT kelliejenkinson nalkylationoffunctionalizedamineswithalcoholsusingacoppergoldmixedphotocatalyticsystem AT andrewehwheatley nalkylationoffunctionalizedamineswithalcoholsusingacoppergoldmixedphotocatalyticsystem AT susumusaito nalkylationoffunctionalizedamineswithalcoholsusingacoppergoldmixedphotocatalyticsystem AT hiroshinaka nalkylationoffunctionalizedamineswithalcoholsusingacoppergoldmixedphotocatalyticsystem
_version_	1718387922685657088

N-Alkylation of functionalized amines with alcohols using a copper–gold mixed photocatalytic system

Ejemplares similares