Diverse secondary C(sp(3))–H bond functionalization via site-selective trifluoroacetoxylation of aliphatic amines

We describe a coinage-metal-catalyzed site-selective oxidation of secondary C(sp(3))–H bonds for aliphatic amine substrates. Broad amine scope, good functional compatibility and late-stage diversification are demonstrated with this method. The steric demand of the β-substituents controlled diastereo...

Descripción completa

Detalles Bibliográficos
Autores principales: Tang, Yongzhen, Qin, Yuman, Meng, Dongmei, Li, Chaoqun, Wei, Junfa, Yang, Mingyu
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2018
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6115674/
https://www.ncbi.nlm.nih.gov/pubmed/30310565
http://dx.doi.org/10.1039/c8sc01788c
_version_ 1783351434932125696
author Tang, Yongzhen
Qin, Yuman
Meng, Dongmei
Li, Chaoqun
Wei, Junfa
Yang, Mingyu
author_facet Tang, Yongzhen
Qin, Yuman
Meng, Dongmei
Li, Chaoqun
Wei, Junfa
Yang, Mingyu
author_sort Tang, Yongzhen
collection PubMed
description We describe a coinage-metal-catalyzed site-selective oxidation of secondary C(sp(3))–H bonds for aliphatic amine substrates. Broad amine scope, good functional compatibility and late-stage diversification are demonstrated with this method. The steric demand of the β-substituents controlled diastereoselectivities under this catalytic system. The site selectivity favors secondary C(sp(3))–H bonds over tertiary ones underscoring the unique synthetic potential of this method.
format Online
Article
Text
id pubmed-6115674
institution National Center for Biotechnology Information
language English
publishDate 2018
publisher Royal Society of Chemistry
record_format MEDLINE/PubMed
spelling pubmed-61156742018-10-11 Diverse secondary C(sp(3))–H bond functionalization via site-selective trifluoroacetoxylation of aliphatic amines Tang, Yongzhen Qin, Yuman Meng, Dongmei Li, Chaoqun Wei, Junfa Yang, Mingyu Chem Sci Chemistry We describe a coinage-metal-catalyzed site-selective oxidation of secondary C(sp(3))–H bonds for aliphatic amine substrates. Broad amine scope, good functional compatibility and late-stage diversification are demonstrated with this method. The steric demand of the β-substituents controlled diastereoselectivities under this catalytic system. The site selectivity favors secondary C(sp(3))–H bonds over tertiary ones underscoring the unique synthetic potential of this method. Royal Society of Chemistry 2018-06-28 /pmc/articles/PMC6115674/ /pubmed/30310565 http://dx.doi.org/10.1039/c8sc01788c Text en This journal is © The Royal Society of Chemistry 2018 http://creativecommons.org/licenses/by-nc/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported Licence (CC BY-NC 3.0)
spellingShingle Chemistry
Tang, Yongzhen
Qin, Yuman
Meng, Dongmei
Li, Chaoqun
Wei, Junfa
Yang, Mingyu
Diverse secondary C(sp(3))–H bond functionalization via site-selective trifluoroacetoxylation of aliphatic amines
title Diverse secondary C(sp(3))–H bond functionalization via site-selective trifluoroacetoxylation of aliphatic amines
title_full Diverse secondary C(sp(3))–H bond functionalization via site-selective trifluoroacetoxylation of aliphatic amines
title_fullStr Diverse secondary C(sp(3))–H bond functionalization via site-selective trifluoroacetoxylation of aliphatic amines
title_full_unstemmed Diverse secondary C(sp(3))–H bond functionalization via site-selective trifluoroacetoxylation of aliphatic amines
title_short Diverse secondary C(sp(3))–H bond functionalization via site-selective trifluoroacetoxylation of aliphatic amines
title_sort diverse secondary c(sp(3))–h bond functionalization via site-selective trifluoroacetoxylation of aliphatic amines
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6115674/
https://www.ncbi.nlm.nih.gov/pubmed/30310565
http://dx.doi.org/10.1039/c8sc01788c
work_keys_str_mv AT tangyongzhen diversesecondarycsp3hbondfunctionalizationviasiteselectivetrifluoroacetoxylationofaliphaticamines
AT qinyuman diversesecondarycsp3hbondfunctionalizationviasiteselectivetrifluoroacetoxylationofaliphaticamines
AT mengdongmei diversesecondarycsp3hbondfunctionalizationviasiteselectivetrifluoroacetoxylationofaliphaticamines
AT lichaoqun diversesecondarycsp3hbondfunctionalizationviasiteselectivetrifluoroacetoxylationofaliphaticamines
AT weijunfa diversesecondarycsp3hbondfunctionalizationviasiteselectivetrifluoroacetoxylationofaliphaticamines
AT yangmingyu diversesecondarycsp3hbondfunctionalizationviasiteselectivetrifluoroacetoxylationofaliphaticamines

Ejemplares similares