Publication

Palladium(II)-Catalyzed Cyclizative Cross-Coupling of ortho-Alkynylanilines with ortho-Alkynylbenzamides under Aerobic Conditions

Qian Wang, Jieping Zhu, Bo Yao
2013
Journal Articles

Abstract

Born to couple: The Pd(OAc)2-catalyzed reaction of o-alkynylanilines (1) with oalkynylbenzamides (2) affords the cyclizative cross-coupling products 3 in good to excellent yields. Three bonds are created in the formation of two heterocycles tethered by a tetra substituted double bond. Mechanistic studies indicate that the reaction is initiated by aminopalladation with subsequent oxypalladation, N-demethylation, and reductive elimination

Official source

https://infoscience.epfl.ch/entities/publication/59ba3371-01c2-40ac-a33d-c1db5f69c635

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Qian Wang, Jieping Zhu, Bo Yao
2013
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/59ba3371-01c2-40ac-a33d-c1db5f69c635

About this result

Related concepts (5)

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.

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.

Reductive elimination

Reductive elimination is an elementary step in organometallic chemistry in which the oxidation state of the metal center decreases while forming a new covalent bond between two ligands. It is the microscopic reverse of oxidative addition, and is often the product-forming step in many catalytic processes. Since oxidative addition and reductive elimination are reverse reactions, the same mechanisms apply for both processes, and the product equilibrium depends on the thermodynamics of both directions.

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