Lecture

C-C Bond Formation: Catalytic Strategies

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In course

CH-223: Organometallic chemistry

Basic organometallic chemistry will be covered in this course.

Structure and bonding in organometallic compounds.
reactivity of organometallic compounds, stoichiometric reactions, catalyzed reactions and reaction mechanisms. ...

Description

This lecture covers the catalytic strategies for making C-C bonds, focusing on the Heck coupling reaction and other related couplings like Suzuki and Sonogashira. It discusses the mechanisms, intermediates, and key factors influencing the reactions, as well as the applications and limitations of these catalytic processes, emphasizing the importance of stereochemistry and the need for considering purification methods and potential issues with metal catalysts.

Instructors (2)

Marinella Mazzanti

Expertise Inorganic Chemistry, Coordination ChemistryF-elements Chemistry Teaching & PhD Past EPFL PhD Students Julie Renée Michelle Andrez, Marta Falcone, Radmila Faizova, Davide Toniolo, Luciano Barluzzi, Aurélien René Willauer, Nadir Jori, Dieuwertje Katelijn Modder, Hsueh Fang-Che, Keerthi Shivaraam Rangaraj Ananthakumar, Mikhail Batov Past EPFL PhD Students as codirector Andreichenko Andrei Courses Chemistry of f elements CH-427 The course will provide a synopsis of the chemistry of f e

Felix Daniel Bobbink

Official source

Ontological neighbourhood

Chemistry

Organic chemistry: Organometallic chemistry

Related concepts (32)

Kumada coupling

In organic chemistry, the Kumada coupling is a type of cross coupling reaction, useful for generating carbon–carbon bonds by the reaction of a Grignard reagent and an organic halide. The procedure uses transition metal catalysts, typically nickel or palladium, to couple a combination of two alkyl, aryl or vinyl groups. The groups of Robert Corriu and Makoto Kumada reported the reaction independently in 1972. The reaction is notable for being among the first reported catalytic cross-coupling methods.

Sonogashira coupling

The Sonogashira reaction is a cross-coupling reaction used in organic synthesis to form carbon–carbon bonds. It employs a palladium catalyst as well as copper co-catalyst to form a carbon–carbon bond between a terminal alkyne and an aryl or vinyl halide. R1: aryl or vinyl R2: arbitrary X: I, Br, Cl or OTf The Sonogashira cross-coupling reaction has been employed in a wide variety of areas, due to its usefulness in the formation of carbon–carbon bonds.

Suzuki reaction

The Suzuki reaction is an organic reaction, classified as a cross-coupling reaction, where the coupling partners are a boronic acid and an organohalide and the catalyst is a palladium(0) complex. It was first published in 1979 by Akira Suzuki, and he shared the 2010 Nobel Prize in Chemistry with Richard F. Heck and Ei-ichi Negishi for their contribution to the discovery and development of palladium-catalyzed cross-couplings in organic synthesis. This reaction is also known as the Suzuki–Miyaura reaction or simply as the Suzuki coupling.

Cross-coupling reaction

In organic chemistry, a cross-coupling reaction is a reaction where two different fragments are joined. Cross-couplings are a subset of the more general coupling reactions. Often cross-coupling reactions require metal catalysts. One important reaction type is this: (R, R' = organic fragments, usually aryle; M = main group center such as Li or MgX; X = halide) These reactions are used to form carbon–carbon bonds but also carbon-heteroatom bonds. Cross-coupling reaction are a subset of coupling reactions.

Bond energy

In chemistry, bond energy (BE), also called the mean bond enthalpy or average bond enthalpy is a measure of bond strength in a chemical bond. IUPAC defines bond energy as the average value of the gas-phase bond-dissociation energy (usually at a temperature of 298.15 K) for all bonds of the same type within the same chemical species. The bond dissociation energy (enthalpy) is also referred to as bond disruption energy, bond energy, bond strength, or binding energy (abbreviation: BDE, BE, or D).

Related lectures (37)

Cross-Coupling of Organometallics

Covers versatile methods for C-C bond formation using different organometallic reagents and organic halides.

Transition Metal Catalysis: Kumada Coupling

Explores the history and significance of the Kumada Coupling reaction in transition metal catalysis.

V-Cross Couplings: Suzuki Stille Coupling

Covers the principles and mechanisms of V-cross couplings, focusing on Suzuki and Stille couplings.

Rétrosynthèse: Disconnections C-C to Functional Groups

Covers retrosynthesis principles, cross couplings, and functional group disconnections.

Cross-Coupling Reactions: Ligand Effects