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Dess-Martin periodinane: The 'magic wand' in Organic Synthesis

Jul 2，2024

Introduction

In the magical world of chemistry, there is a magical reagent, which has become the "magic wand" in the hands of organic synthetic chemists with its powerful oxidation ability and high selectivity. It is the Dess-Martin periodinane, an oxidant widely used in the field of organic synthesis. This article will guide you into the chemical world of Dess-Martin periodinane with, an in-depth analysis of their chemical properties, synthesis methods, application scenarios, and future development trends.¹

Overview

Dess-Martin periodinane, C₆H₅C(NO₂)₂CH₂OH, is a colorless to light yellow crystalline or powdered substance. It has a strong oxidation ability and can efficiently oxidize a variety of organic compounds, such as alcohols, aldehydes, ketones, and so on. Dess-Martin periodinane is widely used in organic synthesis, especially in drug synthesis, the fine chemical industry, bioactive substance synthesis, and other fields that play an important role.²

Chemical properties

Dess-Martin periodinane has a strong oxidation ability and can react with many organic compounds. Its oxidation mechanism is mainly through the oxidation of high iodoalkane, the hydroxyl or aldehyde group in alcohol, aldehydes, ketones, and other organic compounds is oxidized to the carbonyl group, to generate the corresponding ketone or acid. Its oxidation reaction is highly selective and efficient, and it can realize the oxidation transformation of organic compounds under relatively mild conditions.³

Synthesis method

There are two main methods for the synthesis of Dess-Martin periodinane: one is direct synthesis, and the other is obtained by the reaction of iodobenzoic acid with peroxide. Direct synthesis usually takes o-iodobenzoic acid and peroxide as raw materials and reacts under appropriate conditions to obtain Dess-Martin periodinane. This method is simple to operate, but the cost of raw materials is high. The other method is the reaction of iodobenzoic acid with peroxide to obtain Dess-Martin periodinane, which is easy to obtain raw materials, but the reaction conditions are more severe.⁴

Application Scenarios

Field of organic synthesis

Dess-Martin periodinane is widely used in the field of organic synthesis. It can oxidize alcohols to aldehydes or ketones, and oxidize aldehydes to acids to achieve oxidative transformation of organic compounds. In addition, it can also be used in the synthesis of aldehyde condensation reactions, the synthesis of aromatic ketones, and other reactions to promote the chemical reaction. In drug synthesis, it is often used to synthesize intermediates or structural modules of drugs, to realize the design and development of new drugs.⁵

Fine chemical industry

In the field of fine chemicals, Dess-Martin periodinane are also widely used. It can be used to prepare key intermediates in fine chemical products such as spices, dyes, and coatings. Through its oxidation, the structural transformation and performance improvement of organic compounds can be achieved, thus meeting the needs of fine chemical products.

Synthesis of bioactive substances

Dess-Martin periodinane also has potential applications in the synthesis of bioactive substances. It can be used to synthesize biologically active compounds, such as drugs, pesticides, biological probes, etc. Through its oxidation, the structure transformation and performance optimization of bioactive substances can be realized, thus improving their biological activity and application value.

Use precautions

Although the Dess-Martin periodinane has a wide range of application prospects in organic synthesis, there are also some things to pay attention to in the process of use. First of all, it has strong oxidation and a certain oxidation capacity for most organic matter. Therefore, it is necessary to avoid contact with flammable, explosive, and other substances during use to avoid danger. Second, it is sensitive to light and humidity and needs to be stored in a sealed environment away from light. In addition, it is also necessary to pay attention to the control of reaction conditions during use to ensure the efficiency and safety of the reaction.

Conclusion and Prospect

As an important organic oxidizer, Dess-Martin periodinane has wide application prospects in organic synthesis, the fine chemical industry, bioactive substance synthesis, and other fields. With the continuous development of science and technology and the expansion of application fields, its research and application will also usher in new development opportunities. In the future, we can expect to make more breakthroughs in the optimization of synthetic methods and the development of new applications, which will inject new vitality into the wide application of Dess-Martin periodinane.

References:

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[2] T. BACH S K. Synthesis of 6-Substituted 4-Hydroxy-2-pyrones from Aldehydes by Addition of an Acetoacetate Equivalent, Dess-Martin Oxidation and Subsequent Cyclization[J]. Synlett, 2010, 25 1: 577-592. DOI:10.1055/s-2001-18759.

[3] RANDY SANICHAR . Dess–Martin periodinane oxidative rearrangement for preparation of α-keto thioesters1[J]. Organic & Biomolecular Chemistry, 2018, 16 4: 510-664. DOI:10.1039/c7ob02959d.

[4] CHUNMEI YANG. Dess-Martin Periodinane-Mediated Oxidative Coupling Reaction of Isoquinoline with Benzyl Bromide.[J]. Molecules, 2023, 28 3. DOI:10.3390/molecules28030923.

[5] ANTHONY G. M. BARRETT M O Dieter Hamprecht. Dess?Martin Periodinane Oxidation of Alcohols in the Presence of Stabilized Phosphorus Ylides: A Convenient Method for the Homologation of Alcohols via Unstable Aldehydes[J]. Journal of Organic Chemistry, 1997, 62 26: 8962-9388. DOI:10.1021/jo971569u.