β-Lactam and penicillin substituted mesoionic metal carbene complexes

1,2,3-Triazolylidene MIC M-complexes (M = Au, Pd, Pt) having 2-azetidinones and penicillin G substituents at the triazole ring were prepared by CuAAC on 2-azetidinones having a terminal alkyne tethered at N1, followed by alkylation of the 1,2,3-triazole ring and transmetallation [Au(I), Pd(II) and P...

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Published in:Organic & biomolecular chemistry 2022-03, Vol.20 (13), p.2651-2660
Main Authors: Avello, Marta G, Moreno-Latorre, María, de la Torre, María C, Casarrubios, Luis, Gornitzka, Heinz, Hemmert, Catherine, Sierra, Miguel A
Format: Article
Language:English
Subjects:
Alkylation
Alkynes
Amides
Antibiotics
beta-Lactams
Catalysts
Chemical Sciences
Coordination chemistry
Coordination Complexes
Coordination compounds
Gold
Hydrosilylation
Isomerization
Methane - analogs & derivatives
Palladium
Penicillin
Penicillins
Platinum
Triazoles
β-Lactam antibiotics
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Summary:1,2,3-Triazolylidene MIC M-complexes (M = Au, Pd, Pt) having 2-azetidinones and penicillin G substituents at the triazole ring were prepared by CuAAC on 2-azetidinones having a terminal alkyne tethered at N1, followed by alkylation of the 1,2,3-triazole ring and transmetallation [Au(I), Pd(II) and Pt(II)]. The Au-MIC complexes efficiently catalyze the regioselective cycloisomerization of enynes, while the Pt-MIC complexes were efficient catalysts in hydrosilylation reactions.
ISSN:1477-0520
1477-0539
DOI:10.1039/d2ob00216g