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Related Concept Videos

Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration02:40

Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration

Introduction
Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of alkynes produces different products such as aldehydes and ketones.
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

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.
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
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Electrophilic Addition to Alkynes: Halogenation

Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

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.
Pericyclic Reactions: Introduction01:17

Pericyclic Reactions: Introduction

Pericyclic reactions are organic reactions that occur via a concerted mechanism without generating any intermediates. The reactions proceed through the movement of electrons in a closed loop to form a cyclic transition state, where rearrangement of the σ and π bonds yields specific products.
Pericyclic reactions can be classified into three categories: electrocyclic reactions, cycloaddition reactions, and sigmatropic rearrangements. Electrocyclic reactions and sigmatropic rearrangements are...

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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions
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Ag-Catalyzed Multicomponent Reaction To Access 9-Phosphorylated Xanthenes.

Xiao-Hong Wei1, Xiu-Mei Jiang1, Xu Guo1

  • 1Key Laboratory for Utility of Environment-Friendly Composite Materials and Biomass in University of Gansu Province, College of Chemical Engineering, Northwest Minzu University, No. 1, Northwest Xincun, Lanzhou, 730030, P. R. China.

Organic Letters
|June 29, 2026
PubMed
Summary
This summary is machine-generated.

This study introduces an efficient silver-catalyzed reaction for synthesizing 9-phosphorylated xanthenes from readily available starting materials. This novel method offers a highly atom- and step-economical route to complex molecules.

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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Catalysis

Background:

  • Xanthene derivatives are important scaffolds in medicinal chemistry.
  • Efficient synthesis of multisubstituted xanthenes remains a challenge.

Purpose of the Study:

  • To develop a novel, efficient multicomponent reaction for synthesizing 9-phosphorylated xanthenes.
  • To explore a new synthetic strategy for constructing complex xanthene structures.

Main Methods:

  • A silver-catalyzed multicomponent reaction involving 2-hydroxybenzaldehyde, secondary phosphine oxides, and β-alkynyl ketones.
  • Mechanistic studies to elucidate the reaction pathway.

Main Results:

  • Efficient synthesis of various 9-phosphorylated xanthenes in moderate to good yields.
  • The reaction is highly atom- and step-economical.
  • Mechanistic studies revealed a sequence of phospha-aldol, alkylation, cyclization, dehydration, and cyclization.

Conclusions:

  • A novel and efficient synthetic strategy for multisubstituted 9-phosphorylated xanthenes has been established.
  • The developed method offers a valuable tool for accessing complex xanthene derivatives.
  • The reaction's efficiency and atom-economy make it attractive for further applications.