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Hydroboration-Oxidation of Alkenes

Hydroboration-Oxidation of Alkenes

In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

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.

Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate

Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate

Alkenes can be dihydroxylated using potassium permanganate. The method encompasses the reaction of an alkene with a cold, dilute solution of potassium permanganate under basic conditions to form a cis-diol along with a brown precipitate of manganese dioxide.

Oxidation of Alcohols

Oxidation of Alcohols

In this lesson, the oxidation of alcohols is discussed in depth. The various reagents used for oxidation of primary and secondary alcohols are detailed, and their mechanism of action is provided.
The process of oxidation in a chemical reaction is observed in any of the three forms:

Hydrogen Bonds

Hydrogen Bonds

Hydrogen bonds are weak attractions between atoms that have formed other chemical bonds. One of these atoms is electronegative, like oxygen, and has a partial negative charge. The other is a hydrogen atom that has bonded with another electronegative atom and has a partial positive charge.
Hydrogen Bonds Control the World!
Because hydrogen has very weak electronegativity when it binds with a strongly electronegative atom, such as oxygen or nitrogen, electrons in the bond are unequally shared....

Hydrogen Bonds

Hydrogen Bonds

A hydrogen bond is formed when a weakly positive hydrogen atom already bonded to one electronegative atom (for example, the oxygen in the water molecule) is attracted to another electronegative atom from another polar molecule, such as water (H2O), hydrogen fluoride (HF), or ammonia (NH3). The huge electronegativity difference between the H atom (2.1) and the atom to which it is bonded (4.0 for an F atom, 3.5 for an O atom, or 3.0 for an N atom), combined with the very small size of an H atom...

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Hydrogen Atom Transfer Oxidation by a Gold-Hydroxide Complex.

Marta Lovisari¹, Aidan R McDonald¹

¹School of Chemistry, Trinity College Dublin, The University of Dublin, College Green, Dublin 2, Ireland.

Inorganic Chemistry

|March 4, 2020

Summary

This summary is machine-generated.

Gold(III)-oxygen complexes can oxidize C-H and O-H bonds via hydrogen atom transfer. This study explores their catalytic potential, revealing stable radicals in alcohol oxidation, highlighting proton-coupled electron transfer capabilities.

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Area of Science:

Inorganic Chemistry
Catalysis
Oxidation Reactions

Background:

Gold(III)-oxygen adducts are proposed intermediates in gold-catalyzed oxidation reactions.
The reactivity and mechanistic pathways of these adducts remain largely unexplored.
Understanding these intermediates is crucial for advancing homogeneous and heterogeneous gold oxidation catalysis.

Purpose of the Study:

To investigate the reactivity of a specific Gold(III)-oxygen adduct, complex 1 ([AuIII(OH)(terpy)](ClO4)2).
To elucidate the mechanism by which complex 1 oxidizes substrates with C-H and O-H bonds.
To explore the potential of late transition metal-oxygen adducts in catalytic oxidation processes.

Main Methods:

Synthesis and characterization of the Gold(III)-oxygen adduct.
Kinetic analysis of substrate oxidation reactions.
Detection and quantification of reaction products, including stable radicals.

Main Results:

Complex 1 readily oxidized substrates containing C-H and O-H bonds.
Kinetic studies confirmed a hydrogen atom transfer (HAT) mechanism for the oxidation.
Stable radicals were identified as products from the near-quantitative HAT oxidation of alcohols by complex 1.

Conclusions:

Gold(III)-oxygen adducts can serve as effective oxidants, likely playing a role in gold-catalyzed oxidation reactions.
The study demonstrates the capability of late transition metal-oxygen adducts to facilitate proton-coupled electron transfer (PCET) reactions.
Findings provide insights into the mechanistic underpinnings of gold-mediated oxidations and broaden the scope of known catalytic pathways.