Related Experiment Video
Updated: Mar 13, 2026
09:58
Light-driven Enzymatic Decarboxylation
Published on: May 22, 2016
12.4K
Selective Oxidative Esterification from Two Different Alcohols via Photoredox Catalysis
Hong Yi1, Xia Hu1, Changliang Bian1
1College of Chemistry and Molecular Sciences, The Institute for Advanced Studies (IAS), Wuhan University, Wuhan, 430072, Hubei, P.R. China.
Chemsuschem
|October 30, 2016
Summary
This study presents a mild photocatalysis method for synthesizing esters from alcohols using oxygen. The direct oxidative esterification works under neutral conditions and tolerates various alcohol types.
Area of Science:
- Organic Chemistry
- Photocatalysis
- Sustainable Chemistry
Background:
- Esters are crucial building blocks in the chemical industry and research.
- Direct oxidative esterification using alcohols and O2 is highly desirable but challenging.
- Existing methods often require harsh conditions or complex reagents.
Purpose of the Study:
- To develop a mild and efficient method for direct oxidative esterification.
- To utilize photocatalysis for activating dioxygen (O2) for ester synthesis.
- To achieve ester synthesis from two different alcohols under neutral conditions.
Main Methods:
- Employing photocatalysis to activate molecular oxygen (O2).
- Conducting the esterification reaction under neutral conditions.
- Utilizing readily available alcohols as starting materials.
Main Results:
- Successful synthesis of esters from various alcohols, including primary and secondary types.
- Demonstrated tolerance for long-chain alcohols in the reaction system.
- Achieved direct oxidative esterification using O2 as the terminal oxidant.
Conclusions:
- Photocatalysis offers a mild and simple approach for ester synthesis.
- The developed method provides an appealing alternative for producing esters.
- The system is versatile, accommodating a range of alcohol substrates.
Related Concept Videos
02:44Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
13.3K
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.
13.3K
03:08Hydroboration-Oxidation of Alkenes
12.0K
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.
12.0K
02:37Oxidation of Alcohols
17.4K
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:
The process of oxidation in a chemical reaction is observed in any of the three forms:
17.4K
02:57Sharpless Epoxidation
5.3K
The conversion of allylic alcohols into epoxides using the chiral catalyst was discovered by K. Barry Sharpless and is known as Sharpless epoxidation. The use of a chiral catalyst enables the formation of one enantiomer of the product in excess. This chiral catalyst is mainly a chiral complex of titanium tetraisopropoxide and tartrate ester (specific stereoisomer). The stereoisomer used in the chiral catalyst dictates the formation of the enantiomer of the product. In other words, the use of...
5.3K
02:04Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
7.8K
Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
7.8K
02:17Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
4.0K
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...
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...
4.0K