Gold() catalysed regio- and stereoselective intermolecular hydroamination of internal alkynes: towards functionalised azoles

Gold( i ) catalysed regio- and stereoselective intermolecular hydroamination of internal alkynes was developed for the effective synthesis of a series of ( Z )-functionalised vinylazoles under solvent free conditions. The catalytic hydrogenation of the resulting enamines leads to substituted saturat...

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Published inOrganic & biomolecular chemistry Vol. 17; no. 15; pp. 385 - 3811
Main Authors Michon, Christophe, Gilbert, Joachim, Trivelli, Xavier, Nahra, Fady, Cazin, Catherine S. J, Agbossou-Niedercorn, Francine, Nolan, Steven P
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 10.04.2019
Royal Society of Chemistry
Subjects
Alkynes
Azoles
Catalysis
Chemical Sciences
Chemistry
Chemistry, Organic
Gold
Heterocyclic compounds
NMR
Nuclear magnetic resonance
Organic chemistry
Physical Sciences
Science & Technology
Stereoselectivity
GENERAL CATALYST
MOLECULAR-STRUCTURE
REACTION-MECHANISM
ANTIFUNGAL ACTIVITY
PENDANT ETHER
ASYMMETRIC INTRAMOLECULAR HYDROAMINATION
TERMINAL ALKYNES
CYCLOPENTADIENYL LIGAND
PROTON-TRANSFER
C-H ACTIVATION
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Summary:Gold( i ) catalysed regio- and stereoselective intermolecular hydroamination of internal alkynes was developed for the effective synthesis of a series of ( Z )-functionalised vinylazoles under solvent free conditions. The catalytic hydrogenation of the resulting enamines leads to substituted saturated azoles in good yields. Vinyl- and saturated azoles were synthesised through gold( i ) catalysed regio- and stereoselective intermolecular hydroamination of internal alkynes and subsequent hydrogenation.
Bibliography:Electronic supplementary information (ESI) available: Fig. S1 and S2, Table S1, synthetic and catalytic details, and NMR spectra of all products. See DOI
10.1039/c9ob00587k
ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1477-0520
1477-0539
DOI:10.1039/c9ob00587k