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Metal-Ligand Bonds

Metal-Ligand Bonds

The hemoglobin in the blood, the chlorophyll in green plants, vitamin B-12, and the catalyst used in the manufacture of polyethylene all contain coordination compounds. Ions of the metals, especially the transition metals, are likely to form complexes.
In these complexes, transition metals form coordinate covalent bonds, a kind of Lewis acid-base interaction in which both of the electrons in the bond are contributed by a donor (Lewis base) to an electron acceptor (Lewis acid). The Lewis acid in...

Complexation Equilibria: The Chelate Effect

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In complexation reactions, metal atoms or cations interact with ligands to form donor-acceptor adducts called metal complexes. Ligands that bind through one donor site are monodentate, ligands with two donor sites are bidentate, and those with more than two donor sites are polydentate ligands. For example, ethylene diamine is a bidentate ligand that binds through two nitrogen donor atoms, forming a five-membered ring. EDTA is a polydentate ligand that binds through four oxygen and two nitrogen...

Regioselectivity and Stereochemistry of Hydroboration

Regioselectivity and Stereochemistry of Hydroboration

A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...

Radical Substitution: Allylic Bromination

Radical Substitution: Allylic Bromination

In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...

Halogenation of Alkenes

Halogenation of Alkenes

Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.

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Updated: Jan 12, 2026

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions

Published on: March 20, 2014

Ligand-Controlled Chemodivergent Bismuth Catalysis.

Lucas Mele¹, Philipp D Engel^2,3,4, Jamie A Cadge²

¹Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, Mülheim an der Ruhr 45470, Germany.

Journal of the American Chemical Society

|November 7, 2025

Summary

This summary is machine-generated.

This study introduces a bismuth catalyst system that selectively forms C-N or C-O bonds using arylboronic acids and N-fluorosulfonimide derivatives. Ligand design controls the reaction

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Preparation of SNS CobaltII Pincer Model Complexes of Liver Alcohol Dehydrogenase

Preparation of SNS CobaltII Pincer Model Complexes of Liver Alcohol Dehydrogenase

Published on: March 19, 2020

Area of Science:

Organometallic Chemistry
Catalysis
Synthetic Organic Chemistry

Background:

Bismuth catalysis offers a sustainable alternative to precious metal catalysts.
Controlling selectivity in cross-coupling reactions remains a significant challenge in organic synthesis.

Purpose of the Study:

To develop a ligand-controlled chemodivergent bismuth-catalyzed coupling platform.
To achieve selective formation of C(sp2)-N or C(sp2)-O bonds from arylboronic acids and N-fluorosulfonimide derivatives.

Main Methods:

Ligand modulation (electronic and steric properties) of bismuth catalysts.
Experimental stoichiometric studies.
Density Functional Theory (DFT) calculations.
Statistical modeling.

Main Results:

A chemodivergent platform enabling selective C(sp2)-N or C(sp2)-O bond formation was established.
Electron-rich sulfone ligands favored sulfonimide formation (2:1 to >20:1 selectivity).
Electron-deficient sulfoximine ligands favored sulfonimidate formation (5:1 to 15:1 selectivity).

Conclusions:

Ligand properties critically influence bismuth catalyst selectivity in coupling reactions.
Mechanistic studies reveal a high-valent bismuth redox cycle where Bi(V) intermediates and reductive elimination pathways dictate product outcome.
Hypervalency and steric parameters around bismuth are key factors controlling reductive elimination and selectivity.