N‑Arylpyridiniophosphines: Synthesis, Structure, and Applications in Au(I) Catalysis

The synthesis and characterization through NMR and X-ray crystallography of a series of N-arylpyridiniophosphines and their corresponding Au­(I)-derivatives are reported. Because of their acceptor properties, pyridiniophosphines efficiently enhance the electrophilicity of the Au atom in the complexe...

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Bibliographic Details
Published in:ACS catalysis 2018-11, Vol.8 (11), p.10457-10463
Main Authors: Tinnermann, Hendrik, Nicholls, Leo D. M, Johannsen, Tim, Wille, Christian, Golz, Christopher, Goddard, Richard, Alcarazo, Manuel
Format: Article
Language:English
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Summary:The synthesis and characterization through NMR and X-ray crystallography of a series of N-arylpyridiniophosphines and their corresponding Au­(I)-derivatives are reported. Because of their acceptor properties, pyridiniophosphines efficiently enhance the electrophilicity of the Au atom in the complexes they form. In our study, this is translated into higher reactivity of the corresponding Au catalysts, which is demonstrated in two mechanistically differentiated cycloisomerizations. Moreover, the steric protection and probably also the electronic stabilization provided by the N-aryl substituents make the active Au-species more robust and slow down its rate of decay. This allows for an appreciable reduction of the catalyst loadings.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.8b03271