Publication

Remarkable Anion and Cation Effects on Stille Reactions in Functionalised Ionic Liquids

Paul Joseph Dyson, Zhaofu Fei, Dongbin Zhao, Cinzia Chiappe
2006
Journal Articles

Abstract

Task-specific ionic liquids bearing nitrile functional groups attached to the cation and nitrogen-donor-containing anions strongly affect the efficiency of the Stille cross-coupling, influencing the nature of the catalyst and its stability. The relative strengths of the coordinating power of the cations and anions are varied and compared, and under certain conditions nanoparticles are observed.

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https://infoscience.epfl.ch/entities/publication/50b53f53-defb-445a-91f6-a1f4e53b2f0e

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Paul Joseph Dyson, Zhaofu Fei, Dongbin Zhao, Cinzia Chiappe
2006
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/50b53f53-defb-445a-91f6-a1f4e53b2f0e

About this result

Related concepts (19)

Stille reaction

The Stille reaction is a chemical reaction widely used in organic synthesis. The reaction involves the coupling of two organic groups, one of which is carried as an organotin compound (also known as organostannanes). A variety of organic electrophiles provide the other coupling partner. The Stille reaction is one of many palladium-catalyzed coupling reactions. Allyl, alkenyl, aryl, benzyl,acyl halides (Cl, Br, I), pseudohalides (OTf, OPO(OR)2), OAc The R1 group attached to the trialkyltin is normally sp2-hybridized, including vinyl, and aryl groups.

Heck reaction

The Heck reaction (also called the Mizoroki–Heck reaction) is the chemical reaction of an unsaturated halide (or triflate) with an alkene in the presence of a base and a palladium catalyst to form a substituted alkene. It is named after Tsutomu Mizoroki and Richard F. Heck. Heck was awarded the 2010 Nobel Prize in Chemistry, which he shared with Ei-ichi Negishi and Akira Suzuki, for the discovery and development of this reaction.

Transmetalation

Transmetalation (alt. spelling: transmetallation) is a type of organometallic reaction that involves the transfer of ligands from one metal to another. It has the general form: M1–R + M2–R′ → M1–R′ + M2–R where R and R′ can be, but are not limited to, an alkyl, aryl, alkynyl, allyl, halogen, or pseudohalogen group. The reaction is usually an irreversible process due to thermodynamic and kinetic reasons. Thermodynamics will favor the reaction based on the electronegativities of the metals and kinetics will favor the reaction if there are empty orbitals on both metals.

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