Cu-Catalyzed Oxidative 3-Amination of Indoles via Formation of Indolyl(aryl)iodonium Imides Using
Cu catalyst
C–N coupling reaction
hypervalent iodine
indole
o-substituted iodoarene
one-pot reaction
regioselectivity
Journal
Molecules (Basel, Switzerland)
ISSN: 1420-3049
Titre abrégé: Molecules
Pays: Switzerland
ID NLM: 100964009
Informations de publication
Date de publication:
22 Mar 2019
22 Mar 2019
Historique:
received:
27
02
2019
revised:
14
03
2019
accepted:
21
03
2019
entrez:
27
3
2019
pubmed:
27
3
2019
medline:
16
7
2019
Statut:
epublish
Résumé
An oxidative 3-amination of indole derivatives using hypervalent iodine(III) and bissulfonimides, which proceeds via the formation of indolyl(aryl)iodonium imides, was developed. This reaction was followed by an indole-selective copper-catalyzed oxidative C⁻N coupling reaction to obtain 3-amino indole derivatives as single regioisomers.
Identifiants
pubmed: 30909483
pii: molecules24061147
doi: 10.3390/molecules24061147
pmc: PMC6471596
pii:
doi:
Substances chimiques
Imides
0
Indoles
0
Solvents
0
Copper
789U1901C5
Iodine
9679TC07X4
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Références
J Med Chem. 2001 Mar 15;44(6):949-60
pubmed: 11300877
Bioorg Med Chem. 2003 Nov 17;11(23):5293-9
pubmed: 14604693
Bioorg Med Chem. 2007 May 1;15(9):3248-65
pubmed: 17339113
J Med Chem. 2008 Mar 13;51(5):1464-8
pubmed: 18260616
Org Biomol Chem. 2010 Mar 7;8(5):1149-53
pubmed: 20165807
Bioorg Med Chem Lett. 2011 Jan 1;21(1):346-9
pubmed: 21134749
J Am Chem Soc. 2012 Sep 19;134(37):15436-42
pubmed: 22913396
J Am Chem Soc. 2014 May 14;136(19):6920-8
pubmed: 24739120
Chem Commun (Camb). 2015 Feb 11;51(12):2273-6
pubmed: 25556519
Org Biomol Chem. 2016 Mar 21;14(11):3027-30
pubmed: 26911555
Chem Asian J. 2016 Dec 19;11(24):3583-3588
pubmed: 27879062
Org Lett. 2017 Mar 17;19(6):1314-1317
pubmed: 28281340
Chem Commun (Camb). 2018 Apr 24;54(34):4258-4261
pubmed: 29457182
J Org Chem. 2018 Dec 7;83(23):14827-14833
pubmed: 30371085