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Related Concept Videos

Radical Reactivity: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

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Radicals adjacent to electron-donating groups are called nucleophilic radicals. These radicals readily react with electrophilic alkenes. The SOMO–LUMO interactions are the driving force for the reaction, where the high-energy SOMO of the electron-rich, nucleophilic radicals interacts with the low-energy LUMO of the electron-deficient, electrophilic alkenes. Such SOMO–LUMO interactions are the basis of reactive radical traps, affecting the selectivity in radical reactions. For...
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Radicals01:27

Radicals

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Roots, often written as radicals, identify the quantity that must be raised to a specific exponent to produce a given value. A radical expression consists of two main components: the radicand, which is the value placed inside the root symbol, and the index, which indicates the degree of the root being taken. The notation n√a indicates the principal nth root of a. If n equals 2, the operation is the square root, while n = 3 defines the cube root. When n is even, a negative radicand does...
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Radical Reactivity: Electrophilic Radicals01:02

Radical Reactivity: Electrophilic Radicals

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Radicals adjacent to electron‐withdrawing groups are called electrophilic radicals. These radicals readily react with nucleophilic alkenes. For example, the malonate radical, in which the radical center is flanked by two electron‐withdrawing groups, reacts readily with butyl vinyl ether, which consists of an electron‐donating oxygen substituent. The reaction between electrophilic malonate radical and nucleophilic vinyl ether is favored because the radical has a...
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Radical Autoxidation01:20

Radical Autoxidation

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The oxidation of an organic compound in the presence of air or oxygen is called autoxidation. For example, cumene reacts with oxygen to form hydroperoxide. Autoxidation involves initiation, propagation, and termination steps. Many organic compounds are susceptible to autoxidation—especially ethers in the presence of oxygen, which form hydroperoxides. Even though this reaction is slow, old ether bottles contain small amounts of peroxide, which leads to laboratory explosions during ether...
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Radical Equations01:26

Radical Equations

372
Radical equations are mathematical expressions in which the variable is found within a radical, most commonly a square root or cube root. These equations frequently arise in science, engineering, and real-world measurements involving nonlinear relationships. To solve a radical equation, the standard procedure is to isolate the radical expression and then eliminate the radical by raising each side to a power equal to the index of the radical. This process may lead to extraneous...
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Radical Formation: Overview01:03

Radical Formation: Overview

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A bond can be broken either by heterolytic bond cleavage to form ions or homolytic bond cleavage to yield radicals. A fishhook arrow is used to represent the motion of a single electron in homolytic bond cleavage. There are two main sources from which radicals can be formed:
Radicals from spin-paired molecules:
Radicals can be obtained from spin-paired molecules either by homolysis or electron transfer. While two radicals are formed in the former, an electron is added in the...
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Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development
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Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development

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Radical Retrosynthesis.

Joel M Smith1, Stephen J Harwood1, Phil S Baran1

  • 1Department of Chemistry , The Scripps Research Institute , 10550 North Torrey Pines Road , La Jolla , California 93037 , United States.

Accounts of Chemical Research
|August 3, 2018
PubMed
Summary
This summary is machine-generated.

Chemists can simplify complex molecule synthesis by using "ideal" strategies, focusing on direct C-H functionalization and minimizing protecting groups and redox steps. Radical cross-coupling (RCC) methods offer a powerful, albeit less intuitive, approach to achieve these goals.

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Area of Science:

  • Organic Synthesis
  • Retrosynthetic Analysis
  • Green Chemistry

Background:

  • Retrosynthetic analysis, crucial for designing synthetic routes, traditionally relies on "wise" simplifying transforms and polar disconnections.
  • The concept of "ideality" in synthesis emphasizes practicality, scalability, and sustainability by minimizing steps, functional group interconversions, and redox manipulations.
  • Classical methods like cross-coupling and polar additions are widely used, while radical chemistry is often overlooked due to historical perceptions of uncontrollability.

Purpose of the Study:

  • To explore the strategic and tactical advantages of employing one-electron radical cross-coupling (RCC) methods in organic synthesis.
  • To demonstrate how RCC can enable more direct synthetic routes with minimal use of protecting groups and functional group interconversions.
  • To highlight the potential of RCC to overcome limitations of traditional methods and inspire innovative synthetic strategies.

Main Methods:

  • Application of retrosynthetic analysis guided by the principle of "ideality" to identify opportunities for novel transformations.
  • Investigation of both innate and programmed radical cross-coupling (RCC) reactions.
  • Analysis of case studies showcasing the strategic benefits of RCC in diverse synthetic contexts.

Main Results:

  • Radical cross-coupling (RCC) methods offer unique chemoselectivity, enabling syntheses that are more direct and efficient.
  • The use of RCC can significantly reduce the need for protecting group strategies and functional group interconversions.
  • One-electron disconnections, though less intuitive, provide powerful tools for simplifying complex molecular construction.

Conclusions:

  • The strategic application of radical cross-coupling (RCC) methods aligns with the principles of ideal synthesis, leading to more efficient and sustainable routes.
  • Overcoming the historical perception of radicals allows for the integration of RCC into mainstream retrosynthetic planning.
  • RCC represents a valuable complementary approach to traditional methods, driving innovation in complex molecule synthesis.