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Lecture

C-C Bond Formation: Catalytic Strategies

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)

Felix Daniel Bobbink

Marinella Mazzanti

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.

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.

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.

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.

Coupling reaction

In organic chemistry, a coupling reaction is a type of reaction in which two reactant molecules are bonded together. Such reactions often require the aid of a metal catalyst. In one important reaction type, a main group organometallic compound of the type R-M (where R = organic group, M = main group centre metal atom) reacts with an organic halide of the type R'-X with formation of a new carbon-carbon bond in the product R-R'. The most common type of coupling reaction is the cross coupling reaction. Richard F.

Related lectures (30)

Cross-Coupling of Organometallics

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

V-Cross Couplings: Suzuki Stille Coupling

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

Cross-Coupling Reactions: Ligand Effects

Explores the mechanisms and ligand effects in cross-coupling reactions.

Retrosynthesis: Disconnections C-C

Covers the principles of retrosynthesis, focusing on disconnections C-C and functional group disconnections.

Transition Metal Catalysis: Kumada Coupling