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Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

2.7K
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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Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

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Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
2.2K
Carboxylic Acid Derivatives: Overview01:15

Carboxylic Acid Derivatives: Overview

3.9K
Carboxylic acid derivatives are formed by replacing the hydroxyl group of carboxylic acids with a different functional group. The most common carboxylic acid derivatives are:
3.9K
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.1K
Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
2.1K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism01:26

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism

3.5K
The Hofmann and Curtius rearrangement reactions can be applied to synthesize primary amines from carboxylic acid derivatives such as amides and acyl azides. In the Hofmann rearrangement, a primary amide undergoes deprotonation in the presence of a base, followed by halogenation to generate an N-haloamide. A second proton abstraction produces a stabilized anionic species, which rearranges to an isocyanate intermediate via an alkyl group migration from the carbonyl carbon to the neighboring...
3.5K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

3.3K
In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
3.3K

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New synthetic approaches toward OCF3-containing compounds.

Bo-Ya Hao1, Ya-Ping Han1, Yuecheng Zhang1

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Organic & Biomolecular Chemistry
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This review summarizes synthesis strategies for trifluoromethoxylated (OCF3) compounds, crucial in pharmaceuticals and agrochemicals. It covers six key methods for efficiently creating these valuable fluorinated molecules.

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Agrochemistry

Background:

  • Fluorinated organic compounds are essential in various industries.
  • The trifluoromethoxy (OCF3) group offers unique physicochemical properties.
  • OCF3 motifs are prevalent in pharmaceuticals, agrochemicals, and materials.

Purpose of the Study:

  • To review and categorize current synthesis strategies for OCF3-containing compounds.
  • To highlight the importance of OCF3 group installation in drug and agrochemical design.
  • To provide a comprehensive overview of the state-of-the-art in OCF3 synthesis.

Main Methods:

  • Summarizing existing literature on OCF3 synthesis.
  • Categorizing methods into six distinct approaches.
  • Analyzing strategies for *de novo* OCF3 formation and functional group installation.

Main Results:

  • Six main categories of OCF3 synthesis are identified.
  • Methods include direct trifluoromethylation, direct OCF3 group installation, visible-light, and transition metal catalysis.
  • Rearrangement reactions also offer pathways to OCF3 compounds.

Conclusions:

  • Efficient and versatile synthesis of OCF3 compounds is critical for developing new drugs and agrochemicals.
  • The review provides a structured overview of available synthetic methodologies.
  • Continued research in OCF3 synthesis will drive innovation in applied chemistry.