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Open AccessFeature PaperArticle

Polystyrene-Supported Acyclic Diaminocarbene Palladium Complexes in Sonogashira Cross-Coupling: Stability vs. Catalytic Activity

Institute of Chemistry, St. Petersburg State University, 7/9 Universitetskaya nab., St. Petersburg 199034, Russia
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Catalysts 2018, 8(4), 141; https://doi.org/10.3390/catal8040141
Received: 9 March 2018 / Revised: 22 March 2018 / Accepted: 28 March 2018 / Published: 2 April 2018
(This article belongs to the Special Issue Solid-Supported Reagents in Palladium-Catalyzed Transformations)
Two types of immobilized on the amino-functionalized polystyrene-supported acyclic diaminocarbene palladium complexes (ADC-PdII) are investigated under Sonogashira cross-coupling conditions. Depending on substituents in the diaminocarbene fragment immobilized ADC-PdII, systems are found to have different catalytic activity and stability regarding Pd-leaching. PdII-diaminocarbenes possessing protons at both nitrogen atoms smoothly decompose into Pd0-containing species providing a catalytic “cocktail system” with high activity and ability to reuse within nine runs. Polymer-supported palladium (II) complex bearing NBn–Ccarbene–NH-moiety exhibits greater stability while noticeably lower activity under Sonogashira cross-coupling. Four molecular ADC-PdII complexes are also synthesized and investigated with the aim of confirming proposed base-promoted pathway of ADC-PdII conversion through carbodiimide into an active Pd0 forms. View Full-Text
Keywords: palladium; cross-coupling; Sonogashira coupling; carbene; polystyrene; catalyst activation; boomerang mechanism; carbodiimide; isocyanide palladium; cross-coupling; Sonogashira coupling; carbene; polystyrene; catalyst activation; boomerang mechanism; carbodiimide; isocyanide
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Mikhaylov, V.N.; Sorokoumov, V.N.; Liakhov, D.M.; Tskhovrebov, A.G.; Balova, I.A. Polystyrene-Supported Acyclic Diaminocarbene Palladium Complexes in Sonogashira Cross-Coupling: Stability vs. Catalytic Activity. Catalysts 2018, 8, 141.

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