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Lecture

Cross-Coupling of Organometallics

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 Negishi, Suzuki, Stille, and Kumada couplings, which are versatile methods for C-C bond formation using different organometallic reagents and organic halides. The mechanisms, ligand effects, and applications of these reactions are discussed.

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

Ontological neighbourhood

Chemistry

Organic chemistry: Organometallic chemistry

Related concepts (32)

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.

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.

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.

Hiyama coupling

The Hiyama coupling is a palladium-catalyzed cross-coupling reaction of organosilanes with organic halides used in organic chemistry to form carbon–carbon bonds (C-C bonds). This reaction was discovered in 1988 by Tamejiro Hiyama and Yasuo Hatanaka as a method to form carbon-carbon bonds synthetically with chemo- and regioselectivity. The Hiyama coupling has been applied to the synthesis of various natural products.

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.

Related lectures (31)

Transition Metal Catalysis: Kumada Coupling

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

Cross-Coupling Reactions: Ligand Effects

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

V-Cross Couplings: Suzuki Stille Coupling

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

Synthesis of T-Conjugated Molecules

Covers the synthesis of T-conjugated molecules, cross-coupling reactions, polymerization, and band gap tuning.

C-C Bond Formation: Catalytic Strategies