Publication

Nickel-Catalyzed Enantioselective Pyridone C-H Functionalizations Enabled by a Bulky N-Heterocyclic Carbene Ligand

Nicolai Cramer, Johannes Diesel
2018
Journal Articles

Abstract

Annulated pyridones are an importantscaffold found in many biologically active compounds. ANi(0)-catalyzed C−H functionalization of 2- and 4-pyridones is disclosed, providing access to annulatedpyridones via enantioselective intramolecular olefin hydro-arylation. Key to the success of the transformation was thedevelopment of a sterically hindered and tunableN-heterocyclic carbene ligand resembling a chiral version ofIPr. This ligand allows for mild reaction temperatures, andleads to the annulated pyridones in excellent yields andenantioselectivities.

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https://infoscience.epfl.ch/entities/publication/d3c25598-0b7c-4a47-ac70-8425e5c7949f

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Nicolai Cramer, Johannes Diesel
2018
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/d3c25598-0b7c-4a47-ac70-8425e5c7949f

About this result

Related concepts (16)

Ligand

In coordination chemistry, a ligand is an ion or molecule with a functional group that binds to a central metal atom to form a coordination complex. The bonding with the metal generally involves formal donation of one or more of the ligand's electron pairs, often through Lewis bases. The nature of metal–ligand bonding can range from covalent to ionic. Furthermore, the metal–ligand bond order can range from one to three. Ligands are viewed as Lewis bases, although rare cases are known to involve Lewis acidic "ligands".

Functional group

In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the rest of the molecule's composition. This enables systematic prediction of chemical reactions and behavior of chemical compounds and the design of chemical synthesis. The reactivity of a functional group can be modified by other functional groups nearby.

Bridging ligand

In coordination chemistry, a bridging ligand is a ligand that connects two or more atoms, usually metal ions. The ligand may be atomic or polyatomic. Virtually all complex organic compounds can serve as bridging ligands, so the term is usually restricted to small ligands such as pseudohalides or to ligands that are specifically designed to link two metals. In naming a complex wherein a single atom bridges two metals, the bridging ligand is preceded by the Greek letter mu, μ, with a subscript number denoting the number of metals bound to the bridging ligand.

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Nickel-Catalyzed Enantioselective Pyridone C-H Functionalizations Enabled by a Bulky N-Heterocyclic Carbene Ligand

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