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Lecture

Alkene Metathesis: Mechanisms and Applications

In course

CH-422: Catalyst design for synthesis

This course on homogeneous catalysis provide a detailed understanding of how these catalysts work at a mechanistic level and give examples of catalyst design for important reactions (hydrogenation, olefin metathesis, cross-coupling). ...

Description

This lecture covers the mechanisms and applications of alkene metathesis, starting with the pioneering work by Katz in 1985. It discusses the formation of metathesis-active complexes, total synthesis strategies, and the stereochemistry of alkene hydrogenation. The lecture also explores the selectivities of hydrogenation reactions, the Lindlar catalyst for alkynes, and the detailed reaction mechanisms of hydrogenation using Wilkinson's catalyst.

Instructor

Xile Hu

Xile Hu was born in 1978 in Putian, southeastern China. He entered the Peking University in Beijing in 1996. Besides learning too little chemistry, his biggest regret in the college was not able to correct his southern accent in Mandarin. After graduated from PKU, he went to the United States and began his doctoral studies at the University of California, San Diego. In December 2004, he finished with a Ph.D. in chemistry and some fond memories of the beautiful city of San Diego. He then moved to the Los Angeles area and become a postdoctoral scholar at the California Institute of Technology. There he enjoyed numerous stimulating scientific (and other) discussions with friends and colleagues. He also made plenty of friends outside the campus and was a frequent in many local Chinese restaurants. In 2007, after two pleasant visits to Switzerland, he decided to move across the continent one more time and join the faculty of the École Polytechnique Fédérale de Lausanne (EPFL). He now directs the Laboratory of Inorganic Synthesis and Catalysis and is interested in developing chemistry for synthesis, energy and sustainability.

Official source

Related concepts (32)

Hydrogenation

Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to reduce or saturate organic compounds. Hydrogenation typically constitutes the addition of pairs of hydrogen atoms to a molecule, often an alkene. Catalysts are required for the reaction to be usable; non-catalytic hydrogenation takes place only at very high temperatures.

Asymmetric hydrogenation

Asymmetric hydrogenation is a chemical reaction that adds two atoms of hydrogen to a target (substrate) molecule with three-dimensional spatial selectivity. Critically, this selectivity does not come from the target molecule itself, but from other reagents or catalysts present in the reaction. This allows spatial information (what chemists refer to as chirality) to transfer from one molecule to the target, forming the product as a single enantiomer.

Olefin metathesis

Olefin metathesis is an organic reaction that entails the redistribution of fragments of alkenes (olefins) by the scission and regeneration of carbon-carbon double bonds. Because of the relative simplicity of olefin metathesis, it often creates fewer undesired by-products and hazardous wastes than alternative organic reactions. For their elucidation of the reaction mechanism and their discovery of a variety of highly active catalysts, Yves Chauvin, Robert H. Grubbs, and Richard R.

Transfer hydrogenation

In chemistry, transfer hydrogenation is a chemical reaction involving the addition of hydrogen to a compound from a source other than molecular . It is applied in laboratory and industrial organic synthesis to saturate organic compounds and reduce ketones to alcohols, and imines to amines. It avoids the need for high-pressure molecular used in conventional hydrogenation. Transfer hydrogenation usually occurs at mild temperature and pressure conditions using organic or organometallic catalysts, many of which are chiral, allowing efficient asymmetric synthesis.

Alkene

In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond. The double bond may be internal or in the terminal position. Terminal alkenes are also known as α-olefins. The International Union of Pure and Applied Chemistry (IUPAC) recommends using the name "alkene" only for acyclic hydrocarbons with just one double bond; alkadiene, alkatriene, etc., or polyene for acyclic hydrocarbons with two or more double bonds; cycloalkene, cycloalkadiene, etc.

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Catalysis: Hydrogenation

Covers the topic of catalysis, focusing on the process of hydrogenation and the advantages of using soluble catalysts.

Hydrogenation Mechanism

Delves into the detailed reaction mechanism of hydrogenation, emphasizing Wilkinson's catalyst and the impact of ligand design.

Catalytic Functionalization of Olefins

Explores catalytic reactions for olefin functionalization, covering asymmetric allylation, hydrogenation, isomerization, hydroamination, hydroboration, and radical reactions.

Electrophilic Addition: Chemistry of Alkenes and Hydrogenation

Discusses electrophilic addition reactions and hydrogenation processes in alkenes, emphasizing mechanisms, conditions, and practical applications in organic synthesis.

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