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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.

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.

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...

Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration

Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration

Introduction
Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of alkynes produces different products such as aldehydes and ketones.

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 Reactivity: Intramolecular vs Intermolecular

Radical Reactivity: Intramolecular vs Intermolecular

Radical reactions can occur either intermolecularly or intramolecularly. In an intermolecular radical reaction, a nucleophilic radical adds to an electrophilic alkene or vice versa. In such reactions, the radical and generally the alkene, which is also called the radical trap, are two different molecules. Additionally, for such intermolecular reactions to occur, the radical trap must be active, present in an excess concentration, and the radical starting material must have a weak...

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Updated: Sep 5, 2025

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

A redox-enabled strategy for intramolecular hydroamination.

Meredith A Allen¹, Huy M Ly¹, Geneviève F O'Keefe¹

¹Centre for Catalysis Research and Innovation, Department of Chemistry and Biomolecular Sciences, University of Ottawa 10 Marie-Curie Ottawa ON K1N 6N5 Canada andre.beauchemin@uottawa.ca.

Chemical Science

|July 8, 2022

Summary

This summary is machine-generated.

This study introduces a novel, catalyst-free redox strategy for intramolecular hydroamination, simplifying hydroxylamine generation and pyrrolidine N-oxide reduction in one pot. This efficient method offers mild conditions and broad functional group tolerance for synthetic chemists.

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Last Updated: Sep 5, 2025

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

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Published on: January 19, 2016

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

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Published on: August 16, 2018

Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry

Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry

Published on: October 18, 2019

Area of Science:

Organic Chemistry
Synthetic Methodology
Catalysis

Background:

Intramolecular hydroamination reactions, particularly those involving hydroxylamines, face limitations with traditional metal or acid catalysis.
Existing synthetic routes often require harsh conditions or lack functional group tolerance.

Purpose of the Study:

To develop a novel, efficient, and broadly applicable method for intramolecular hydroamination.
To overcome the limitations of existing catalytic approaches by employing a redox-enabled strategy.

Main Methods:

A one-pot, sequential process involving *in situ* generation of hydroxylamines via oxidation.
Subsequent Cope-type intramolecular hydroamination followed by reduction of the pyrrolidine N-oxide intermediate.
Utilizing mild reaction conditions without the need for external catalysts or extensive purification.

Main Results:

The developed redox strategy enables efficient intramolecular hydroamination under mild, catalyst-free conditions.
The process demonstrates high functional group tolerance, simplifying isolation procedures.
A gram-scale example and robustness screening confirm the practical applicability of the method.

Conclusions:

This redox-enabled approach provides a significant advancement in intramolecular hydroamination methodology.
The one-pot, catalyst-free protocol offers a practical and versatile alternative for synthesizing pyrrolidine derivatives.
The method's mildness and functional group tolerance make it valuable for complex molecule synthesis.