Related Experiment Video

Updated: May 15, 2025

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions

Published on: March 20, 2014

Pd-Catalyzed Cross-Coupling of Alkylbisboronic Esters

Philip P Scott¹, Christopher E Baird¹, Elizabeth A Kraichely¹

¹Department of Chemistry and Biochemistry, College of Charleston, 66 George Street, Charleston, SC, 29424, USA.

|April 11, 2025

Summary

This study details a palladium-catalyzed cross-coupling reaction using alkylbisboronic esters and aryl bromides. A two-carbon linker proved optimal for efficient coupling, with the reaction mechanism explored through competition experiments.

Area of Science:

Organic Chemistry
Catalysis

Background:

Cross-coupling reactions are vital in organic synthesis.
Palladium catalysis offers efficient methods for C-C bond formation.

Purpose of the Study:

To develop a Pd-catalyzed cross-coupling method utilizing alkylbisboronic esters and aryl bromides.
To optimize the alkyl chain length for effective coupling.
To investigate the reaction mechanism.

Main Methods:

Palladium-catalyzed cross-coupling reaction.
Systematic variation of alkylbisboronic ester chain lengths.
Competition experiments to elucidate the reaction pathway.

Main Results:

Successful cross-coupling of various aryl bromides with alkylbisboronic esters.
Identification of a two-carbon linker as the optimal chain length.
Insights into the reaction mechanism derived from competition studies.

Conclusions:

A novel Pd-catalyzed cross-coupling method has been established.
The optimal alkyl chain length for efficient coupling was determined.
The mechanistic understanding of this transformation was advanced.

Keywords:

Suzuki alkylboronic esters borons palladium

More Related Videos

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

Published on: April 4, 2014

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

Related Concept Videos

β-Dicarbonyl Compounds via Crossed Claisen Condensations

β-Dicarbonyl Compounds via Crossed Claisen Condensations

Crossed Claisen condensations are base-promoted reactions between two different ester molecules producing β-dicarbonyl compounds. The reaction involving esters, with both containing α hydrogen, results in a mixture of four different products that are difficult to isolate. This reduces the synthetic utility of the reaction.

Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization

Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization

Dieckmann cyclization is an intramolecular Claisen condensation of diesters. The reaction occurs in the presence of a base and generates a cyclic β-ketoester as the final product. Commonly, 1, 6 and 1, 7-diesters are preferred substrates for the reaction since the generated five, and six-membered cyclic β-keto esters are particularly more stable.

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.

Esters to β-Ketoesters: Claisen Condensation Mechanism

Esters to β-Ketoesters: Claisen Condensation Mechanism

Regular Claisen condensation involves the synthesis of β-ketoesters by combining identical ester molecules bearing two α hydrogens in the presence of an alkoxide base. The reaction commences with the deprotonation of the acidic α hydrogen by the base to form a resonance stabilized ester enolate. This nucleophilic ion then attacks the carbonyl center of another ester molecule to generate a tetrahedral alkoxide intermediate. Next, the expulsion of the alkoxide group from the...

α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview

α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview

The pinacol and McMurry reactions involve the reductive coupling of ketones or aldehydes. Similarly, the bimolecular reductive coupling of two ester molecules in the presence of sodium metal in an aprotic solvent yields an α-hydroxy ketone product. The α-hydroxy ketone is also called acyloin, so the reaction is referred to as ‘acyloin condensation.’

Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism

Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism

Carboxylic acids react with alcohols to yield esters via an acid-catalyzed condensation reaction called Fischer esterification. This is a nucleophilic acyl substitution reaction that proceeds via a tetrahedral intermediate, where a water molecule is eliminated as the leaving group.

Articles linked to this work by shared authors, journal, and citation graph.

Chemoselective Benzylation of Aldehydes Using Lewis Base Activated Boronate Nucleophiles.

Organometallics·2019

See all related articles