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Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation

Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation

Baeyer–Villiger oxidation converts aldehydes to carboxylic acids and ketones to esters. The reaction uses peroxy acids or peracids and is often catalyzed by acid. The reaction is named after its pioneers, Adolf von Baeyer and Victor Villiger. The reaction is achieved by a wide range of peracids such as m-chloroperoxybenzoic acid (mCPBA), perbenzoic acid (C6H5COOOH), peracetic acid (CH3COOOH), hydrogen peroxide (H2O2), and tert-butyl hydroperoxide (t-BuOOH).
The carbonyl center is activated by...

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.

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.

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.

Cycloaddition Reactions: Overview

Cycloaddition Reactions: Overview

Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.

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Updated: Dec 14, 2025

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

Published on: June 20, 2014

Scalable biocatalytic C-H oxyfunctionalization reactions.

Suman Chakrabarty¹, Ye Wang, Jonathan C Perkins

¹Life Sciences Institute, University of Michigan, Ann Arbor, MI 48109, USA. arhardin@umich.edu.

Chemical Society Reviews

|July 24, 2020

Summary

Scalable biocatalytic C-H oxyfunctionalization offers a green approach to complex molecule synthesis. This review covers advances in enzymatic methods for preparative-scale C-H oxygenation over the last decade.

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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

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Published on: April 22, 2016

Area of Science:

Organic Chemistry
Biocatalysis
Synthetic Chemistry

Background:

Catalytic C-H oxyfunctionalization streamlines synthesis of complex molecules.
Enzymatic C-H oxygenation complements traditional synthetic methods.
Scalable biocatalysis is crucial for preparative applications.

Purpose of the Study:

To review key advances in scalable biocatalytic C-H oxyfunctionalization.
To highlight progress in the last decade.
To showcase enzymatic approaches for C-H oxygenation.

Main Methods:

Literature review of recent advancements.
Focus on biocatalytic C-H oxyfunctionalization reactions.
Emphasis on scalability and preparative applications.

Main Results:

Significant progress in catalyst design for C-H functionalization.
Development of enzymatic C-H oxygenation methods.
Demonstration of preparative-scale biocatalytic oxyfunctionalization.

Conclusions:

Biocatalytic C-H oxyfunctionalization is a powerful and scalable synthetic tool.
Enzymatic methods offer complementary and efficient routes to complex molecules.
Continued development promises further synthetic innovations.