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Related Concept Videos

Olefin Metathesis Polymerization: Overview01:13

Olefin Metathesis Polymerization: Overview

Recently, the development of olefin metathesis polymerization advanced the field of polymer synthesis. Simply put, the reorganization of substituents on their double bonds between two olefins in the presence of a catalyst is known as the olefin metathesis reaction. The use of metathesis reaction for polymer synthesis is called olefin metathesis polymerization.
Ruthenium-based Grubbs catalyst is the most commonly used catalyst for olefin metathesis polymerization. Grubbs catalyst consists of a...
Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
Preparation of Alkynes: Dehydrohalogenation02:34

Preparation of Alkynes: Dehydrohalogenation

Introduction
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
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.
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)

Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...

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Related Experiment Video

Updated: May 24, 2026

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
19:58

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

Published on: July 30, 2017

Development of palladium-catalyzed transformations using propargylic compounds.

Masahiro Yoshida1

  • 1Graduate School of Pharmaceutical Sciences, The University of Tokushima, Tokushima, Japan. yoshida@ph.tokushima-u.ac.jp

Chemical & Pharmaceutical Bulletin
|March 3, 2012
PubMed
Summary

This study introduces novel palladium-catalyzed reactions using propargylic compounds for stereoselective synthesis of cyclic molecules and allenols. These methods enable efficient CO2 recycling and construction of complex organic structures.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Propargylic compounds with ester and halide groups react with palladium complexes.
  • Palladium complexes form π-propargylpalladium and allenylpalladium intermediates.
  • These intermediates facilitate various chemical transformations.

Purpose of the Study:

  • To develop novel palladium-catalyzed transformations utilizing propargylic compounds.
  • To achieve diastereoselective synthesis of highly substituted cyclic compounds.
  • To develop CO2-recycling reactions for synthesizing cyclic carbonates.

Main Methods:

  • Palladium-catalyzed reactions of propargylic carbonates with bis-nucleophiles (e.g., diones, acetates).
  • Palladium-catalyzed coupling of propargylic oxiranes with arylboronic acids and terminal alkynes.
  • Palladium-catalyzed reactions of propargylic carbonates with phenols for CO2 fixation.

Main Results:

  • Highly substituted cyclic compounds were synthesized with high stereoselectivity.
  • Substituted 4-aryl-2,3-allenols were produced diastereoselectively under mild conditions.
  • Cyclic carbonates were synthesized via a CO2 fixation pathway, achieving diastereoselective, enantioselective, and enantiospecific construction.

Conclusions:

  • Novel palladium-catalyzed reactions offer efficient routes to complex cyclic molecules and allenols.
  • The developed methods allow for stereoselective synthesis and CO2 utilization.
  • These transformations provide valuable tools for organic synthesis.