Publication

Chiral Monodentate Trialkylphosphines Based on the Phospholane Architecture

Nicolai Cramer, Tanguy Jean Daniel Saget, Pavel Alexandrovich Donets
2012
Journal Articles

Abstract

The development of efficient chiral monodentate phosphine ligands lags behind that of the bidentate congeners. This holds especially true for highly electron rich chiral phosphine analogues able to replace the ubiquitous tricyclohexylphosphine and tri-tert-butylphosphine in catalytic asymmetric transformations. We present a convenient and modular synthesis of a set of chiral monodentate ligands with different steric demands based on the popular phospholane scaffold. Their steric and electronic properties were determined by their corresponding nickel and palladium complexes. They represent good mimics of the popular tricyclohexylphosphine and tri-tert-butylphosphine ligands. Their potential was subsequently evaluated in palladium-catalyzed asymmetric C(sp(3))-H functionalization leading to indolines.

Official source

https://infoscience.epfl.ch/entities/publication/01193760-3685-46c0-b68b-70dede92484b

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Nicolai Cramer, Tanguy Jean Daniel Saget, Pavel Alexandrovich Donets
2012
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/01193760-3685-46c0-b68b-70dede92484b

About this result

Related concepts (22)

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".

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.

Tetradentate ligand

In chemistry, tetradentate ligands are ligands that bind four donor atoms to a central atom to form a coordination complex. This number of donor atoms that bind is called denticity and is a method of classifying ligands. Tetradentate ligands are common in nature in the form of chlorophyll, which has a core ligand called chlorin, and heme, which has a core ligand called porphyrin. They are responsible for the colour observed in plants and humans. Phthalocyanine is an artificial macrocyclic tetradentate ligand that is used to make blue and green pigments.

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