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Redox Reactions01:27

Redox Reactions

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Redox reactions are vital biochemical processes that underpin energy metabolism in cells. These reactions involve the transfer of electrons between molecules, occurring in tandem as oxidation and reduction. Oxidation refers to the loss of electrons, while reduction denotes their gain. This coupling ensures the seamless flow of electrons through metabolic pathways. For example, in bacterial metabolism, glucose undergoes oxidation to carbon dioxide, while oxygen is simultaneously reduced to...
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Oxidation-reduction or redox reactions involve the transfer of electrons from one molecule or atom to another. When an atom gains an electron, another atom must lose an electron, meaning oxidation and reduction must occur together. Since the redox occurs in pairs, the atom that gets oxidized is also called the reducing agent or reductant, and the atom that is reduced is also called the oxidizing agent or oxidant. A straightforward way to remember the definitions of oxidation and reduction is...
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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.
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Oxymercuration–reduction of alkenes is one of the major reactions converting alkenes to alcohols. It involves the hydration of alkenes with mercuric acetate in a mixture of tetrahydrofuran and water, forming an organomercury adduct. This is followed by a demercuration step in which the adduct is reduced to an alcohol using sodium borohydride.
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Radical Reactivity: Overview01:11

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Radicals, the highly reactive species, gain stability by undergoing three different reactions. The first reaction involves a radical-radical coupling, in which a radical combines with another radical, forming a spin‐paired molecule. The second reaction is between a radical and a spin‐paired molecule, generating a new radical and a new spin‐paired molecule. The third reaction is radical decomposition in a unimolecular reaction, forming a new radical and a spin‐paired...
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Accelerating Medicinal Chemistry: A C(sp3)-Rich Fragment Toolbox for Redox-Neutral Cross-Coupling.

Jet Tsien1, Áron Péter1, Xin Zeng1

  • 1Department of Chemistry, Scripps Research, 10550 North Torrey Pines Road, La Jolla, CA, 92037, USA.

Angewandte Chemie (International Ed. in English)
|November 10, 2025
PubMed
Summary

Drug discovery synthesis is accelerated using novel sulfonyl hydrazide reagents for mild, nickel-catalyzed cross-coupling of C(sp3)-rich fragments. This approach simplifies analog preparation and improves yields for complex drug candidates.

Keywords:
Heteroaryl Halide FunctionalizationNickel‐catalysisRedox‐neutral Radical CouplingSmall‐fragment Coupling

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Area of Science:

  • Medicinal Chemistry
  • Organic Synthesis
  • Drug Discovery

Background:

  • The hit-to-lead phase is often slowed by analog synthesis, particularly for C(sp3)-rich fragments.
  • Existing methods like Suzuki couplings and radical reactions have limitations including unstable reagents, high costs, and harsh conditions.

Purpose of the Study:

  • To develop a new method for efficient incorporation of small C(sp3)-rich fragments into drug scaffolds.
  • To overcome the limitations of current synthetic strategies in drug discovery.

Main Methods:

  • Development of 15 sulfonyl hydrazide reagents for redox-neutral, nickel-catalyzed radical cross-coupling.
  • Application of the method to over 60 (hetero)aryl halides with diverse functional groups.

Main Results:

  • Successful incorporation of 14 distinct small C(sp3)-rich fragments (e.g., methyl, cyclopropyl, oxetanyl) onto (hetero)arenes under mild conditions.
  • Demonstrated modularity, operational simplicity, and broad substrate scope with high functional group tolerance.
  • Achieved significantly improved yields for key transformations, such as trideuteromethylation and cyclobutylation, compared to existing methods.

Conclusions:

  • The disclosed sulfonyl hydrazide reagents provide a versatile, efficient, and mild platform for synthesizing drug analogs.
  • This method streamlines the incorporation of crucial C(sp3)-rich fragments, accelerating the hit-to-lead process in drug discovery.