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Phosphine-scavenging cationic gold(I) complexes: alternative applications of gold cocatalysis in fundamental palladium-catalyzed cross-couplings

Ho, CC ORCID: 0000-0002-7555-0635, Ariafard, A ORCID: 0000-0003-2383-6380, Hyland, CJT and Bissember, AC ORCID: 0000-0001-5515-2878 2019 , 'Phosphine-scavenging cationic gold(I) complexes: alternative applications of gold cocatalysis in fundamental palladium-catalyzed cross-couplings' , Organometallics, vol. 38, no. 13 , pp. 2683-2688 , doi: 10.1021/acs.organomet.9b00294.

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Abstract

We have demonstrated that air-stable cationic gold(I) cocatalysts have the capacity to enhance the efficiency of palladium-catalyzed cross-couplings. Specifically, we determined that a 1:1 [Pd{P(t-Bu)3}2]/[Au{P(t-Bu)3}(NTf2)] system provides superior reactivity relative to [Pd{P(t-Bu)3}2], across Suzuki–Miyaura, Stille, and Mizoroki–Heck reactions performed under mild conditions. Our results are consistent with cationic gold(I) species serving primarily as phosphine scavengers in this chemistry, as recently predicted by density functional theory (DFT).

Item Type: Article
Authors/Creators:Ho, CC and Ariafard, A and Hyland, CJT and Bissember, AC
Keywords: palladium, gold, cross-coupling, Suzuki-Miyaura, Stille, Mizoroki-Heck
Journal or Publication Title: Organometallics
Publisher: Amer Chemical Soc
ISSN: 0276-7333
DOI / ID Number: 10.1021/acs.organomet.9b00294
Copyright Information:

© 2019 American Chemical Society

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