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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...

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In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.

Heterogeneous Catalysis

Heterogeneous Catalysis

Heterogeneous catalysis involves a catalyst in a different phase from the reactants. It is a process where the catalyst and the reactants are in distinct phases, typically solid and gas or liquid.Most heterogeneous catalysts are metals, metal oxides, or acids. The list includes transition metals like iron (Fe), cobalt (Co), nickel (Ni), palladium (Pd), platinum (Pt), chromium (Cr), manganese (Mn), tungsten (W), silver (Ag), and copper (Cu). These metals possess partially vacant d orbitals that...

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

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The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

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Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.

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Updated: May 16, 2026

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks (MOFs)

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks (MOFs)

Published on: January 17, 2020

Regio- and Site-Selective Organic Synthesis With Single-Atom Catalysts.

Xin Shang¹, Boyu Yu^1,2, Xiang-Ting Min¹

¹CAS Key Laboratory of Science and Technology on Applied Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, China.

Angewandte Chemie (International Ed. in English)

|May 14, 2026

Summary

This summary is machine-generated.

Single-atom catalysts (SACs) offer a heterogeneous approach to selective organic synthesis, overcoming limitations of traditional homogeneous methods. SACs provide tunable electronic properties and confined environments for precise regio- and site-control in various chemical transformations.

Keywords:

heterogeneous catalysis organic synthesis regioselectivity single‐atom catalyst site‐selectivity

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Synthesis and Performance Characterizations of Transition Metal Single Atom Catalyst for Electrochemical CO2 Reduction

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Published on: April 10, 2018

Area of Science:

Catalysis
Materials Science
Organic Chemistry

Background:

Selective organic synthesis is crucial for pharmaceuticals, agrochemicals, and materials.
Homogeneous catalysts with metal-ligand complexes offer selectivity but have limited tuning ranges and require extensive screening.
Ligand design and substituent modification are time-consuming and costly.

Purpose of the Study:

To review recent advances in single-atom catalysts (SACs) for regio- and site-selective transformations.
To discuss the principles of selectivity control offered by SACs.
To outline future opportunities in SACs-catalyzed reactions.

Main Methods:

Heterogeneous catalysis using single-atom catalysts (SACs).
Utilizing support-derived handles for selectivity control.
Tuning electronic structures through metal-support interactions.

Main Results:

SACs enable highly regio- and site-selective hydroformylation, hydrosilylation, hydroboration, hydrogenation, and click chemistry.
SACs offer easy separation and recycling compared to homogeneous catalysts.
Support-derived features provide confined microenvironments and tunable electronic properties.

Conclusions:

SACs present a powerful alternative to homogeneous catalysts for achieving high selectivity in organic synthesis.
The unique properties of SACs, including metal-support interactions and confined environments, are key to their selectivity.
Further research into SACs holds significant promise for developing more efficient and sustainable chemical processes.