2021
DOI: 10.3390/molecules26175220
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Ruthenium Olefin Metathesis Catalysts Featuring N-Heterocyclic Carbene Ligands Tagged with Isonicotinic and 4-(Dimethylamino)benzoic Acid Rests: Evaluation of a Modular Synthetic Strategy

Abstract: A modular and flexible strategy towards the synthesis of N-heterocyclic carbene (NHC) ligands bearing Brønsted base tags has been proposed and then adopted in the preparation of two tagged NHC ligands bearing rests of isonicotinic and 4-(dimethylamino)benzoic acids. Such tagged NHC ligands represent an attractive starting point for the synthesis of olefin metathesis ruthenium catalysts tagged in non-dissociating ligands. The influence of the Brønsted basic tags on the activity of such obtained olefin metathesi… Show more

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Cited by 4 publications
(7 citation statements)
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“…Recently, we developed the practical high-yielding synthesis of racemic salt 1. [23] We realised that it can be utilised in the synthesis of Hoveyda-Grubbs catalyst NHC ligand (Scheme 1). To do so, the free carbene was generated in situ by treatment of 1 with KHMDS and reacted with Hov I to provide "protected" complex 2 in a good yield of 76 %.…”
Section: Resultsmentioning
confidence: 99%
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“…Recently, we developed the practical high-yielding synthesis of racemic salt 1. [23] We realised that it can be utilised in the synthesis of Hoveyda-Grubbs catalyst NHC ligand (Scheme 1). To do so, the free carbene was generated in situ by treatment of 1 with KHMDS and reacted with Hov I to provide "protected" complex 2 in a good yield of 76 %.…”
Section: Resultsmentioning
confidence: 99%
“…Of interest, the same strategy applied not to the Hoveydatype precursor 3 a, but to the related indenylidene complex 3 b failed completely in providing the corresponding acylated complexes (Scheme 2b). [23] Such differences of behaviour between 3 a and 3 b are assumed to rely on the greater stability of phosphine-free complex 3 a under basic conditions required for acylation reaction. Indeed, the decomposition of complex 3 b was systematically observed during all attempted reactions with acyl chloride and the excess of triethylamine in DCM, and even when the corresponding indenylidene complexes were formed, such derivatives degraded quickly during the workup involving column chromatography on silica gel.…”
Section: Resultsmentioning
confidence: 99%
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