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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...
Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview01:27

Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview

Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.
Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
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...
Preparation of Diols and Pinacol Rearrangement01:57

Preparation of Diols and Pinacol Rearrangement

Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
Preparation of Alcohols via Addition Reactions02:15

Preparation of Alcohols via Addition Reactions

Overview
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...

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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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Sustainable Mizoroki-Heck Cross-Coupling Using a Pd(II)-Polymer as Precatalyst in 1‑Butanol.

Elvis Naoto Nishida1, Laíze Zaramello1, Mateus H Keller1

  • 1Department of Chemistry, Federal University of Santa Catarina, Florianópolis, Santa Catarina 88040-900, Brazil.

ACS Omega
|July 3, 2026
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A novel palladium-based polymer catalyst (Pd/PECIm) efficiently drives the Mizoroki-Heck reaction in 1-butanol, offering a sustainable and reusable method for synthesizing valuable organic compounds.

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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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A Simple and Efficient Protocol for the Catalytic Insertion Polymerization of Functional Norbornenes

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Green Chemistry

Background:

  • The Mizoroki-Heck reaction is a cornerstone of C-C bond formation in organic synthesis.
  • Developing sustainable catalytic systems using green solvents is crucial for environmentally friendly chemical processes.
  • Previous work demonstrated the utility of Pd/PECIm in Suzuki-Miyaura reactions.

Purpose of the Study:

  • To investigate the application of a palladium-containing polymeric precatalyst (Pd/PECIm) for the Mizoroki-Heck reaction.
  • To evaluate the performance of Pd/PECIm in various green solvents, focusing on efficiency, stability, and reusability.
  • To optimize reaction conditions for high yield and conversion in the Mizoroki-Heck coupling.

Main Methods:

  • Utilized a palladium-containing polymeric precatalyst (Pd/PECIm).
  • Performed Mizoroki-Heck cross-coupling reactions between iodobenzene and ethyl acrylate in green solvents like water, 2-propanol, and 1-butanol.
  • Optimized reaction parameters including solvent composition, temperature, and catalyst loading.
  • Analyzed catalyst stability, reusability, and product yields.
  • Scaled up the reaction to assess its industrial applicability.

Main Results:

  • Initial attempts in water or 2-propanol yielded low conversion due to polymer degradation and palladium black formation.
  • 1-butanol proved to be a superior solvent, preserving polymer integrity and enabling controlled nanoparticle formation.
  • Optimized conditions achieved 95% conversion to ethyl cinnamate in 1.5 hours with 0.5 mol% Pd.
  • The Pd/PECIm catalyst demonstrated stability and reusability for at least five cycles.
  • The methodology showed a broad substrate scope and was successfully scaled up 50-fold with a 93% yield.

Conclusions:

  • Pd/PECIm in 1-butanol is an efficient, stable, and environmentally friendly precatalyst for Mizoroki-Heck transformations.
  • This system offers a sustainable alternative for the synthesis of cinnamate and stilbene derivatives.
  • The imidization of the polymer matrix in 1-butanol is key to the catalyst's enhanced performance and recyclability.