Suzuki reaction general procedure

Introduction

The Suzuki reaction, also known as the Suzuki-Miyaura cross-coupling reaction, is a widely used method in organic chemistry for forming carbon-carbon bonds. This reaction typically involves the coupling of aryl or vinyl boronic acids with aryl or vinyl halides, catalyzed by palladium. It is highly valued for its efficiency, mild reaction conditions, and broad substrate scope.

Key Insights from Research Papers

Efficiency and Mild Conditions:
- The Suzuki reaction can be performed efficiently under mild conditions using palladium catalysts in aqueous media, often without the need for ligands, resulting in high yields and short reaction times .
- A robust generic protocol has been developed using an air-stable palladium pre-catalyst at low loading in aqueous solvent mixtures, which is effective for a wide range of aryl bromides and chlorides.
Substrate Scope and Selectivity:
- The reaction is versatile, allowing for the synthesis of variously substituted biaryls and polyaryls, including nitrogen-rich heterocycles, under mild conditions with good to excellent yields .
- Chloropyrimidine substrates are preferable over other halogenated pyrimidines for the Suzuki coupling, demonstrating the reaction's adaptability to different substrates.
Green Chemistry and Operational Simplicity:
- The Suzuki reaction can be performed in a green manner, using water as a solvent and mild reaction conditions, making it suitable for educational purposes and industrial applications.
- The development of ligand-free and aqueous-phase reactions further enhances the environmental friendliness and operational simplicity of the Suzuki reaction .
Mechanistic Insights and Visualization:
- Mechanistic studies have provided insights into the inhibitory effects of unprotected azoles on Pd-catalyzed cross-coupling reactions, aiding in the optimization of reaction conditions.
- Real-time visualization techniques, such as surface-enhanced Raman spectroscopy (SERS), have been developed to monitor the Suzuki reaction processes, enhancing the understanding of reaction dynamics.
Specialized Applications:
- Sequential Suzuki coupling reactions have been developed for the synthesis of complex molecules, such as 3,6-disubstituted 2,5-dioxybenzoquinones, demonstrating the reaction's utility in multi-step syntheses.
- Intramolecular B-alkyl Suzuki reactions have been used for transannular macrocyclizations, offering an alternative to ring-closing metathesis for controlling olefin geometry.

Conclusion

The Suzuki reaction is a highly efficient and versatile method for forming carbon-carbon bonds under mild and environmentally friendly conditions. It is adaptable to a wide range of substrates, including nitrogen-rich heterocycles and complex molecules, and can be performed in aqueous media without the need for ligands. Mechanistic insights and real-time visualization techniques have further enhanced the understanding and optimization of this reaction, making it a valuable tool in both academic and industrial settings.

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Suzuki reaction general procedure

Summary

Introduction

Key Insights from Research Papers

Conclusion

Sources and full results

An approach to 3,6-disubstituted 2,5-dioxybenzoquinones via two sequential Suzuki couplings. three-step synthesis of leucomelone.

Two sequential Suzuki coupling reactions efficiently synthesize 3,6-disubstituted 2,5-dioxybenzoquinones, enabling the three-step synthesis of leucomelone in 61% overall yield.

Arylation of halogenated pyrimidines via a Suzuki coupling reaction.

The Suzuki coupling reaction can be used to prepare monophenyl-, diphenyl-, or triphenylpyrimidines, with chloropyrimidine substrates being preferable over iodo, bromo, or fluoropyrimidines.

Synthesis of biaryls and polyaryls by ligand-free Suzuki reaction in aqueous phase.

This study developed a highly efficient palladium acetate-catalyzed ligand-free Suzuki reaction in aqueous phase, enabling the synthesis of biaryls and polyaryls in a single one-pot step under mild reaction conditions (60 degrees C).

Transannular macrocyclization via intramolecular B-alkyl Suzuki reaction.

Intramolecular B-alkyl Suzuki reactions provide high control over olefin geometry, complementing ring closing metathesis macrocyclizations and potentially offering a superior alternative for precise olefin geometry control.

Real-time visualization of the Suzuki reaction using surface enhanced Raman spectroscopy and a moveable magnetic nanoparticle film.

This study successfully developed an operando SERS strategy for real-time visualization of the Suzuki reaction using a moveable magnetic nanoparticle film, proving its feasibility and generality.

Suzuki-Miyaura cross-coupling of unprotected, nitrogen-rich heterocycles: substrate scope and mechanistic investigation.

The Suzuki-Miyaura cross-coupling of nitrogen-rich heterocycles using precatalysts P1 or P2 allows for mild reactions with good to excellent yields, and explains the inhibitory effect of unprotected azoles on Pd-catalyzed cross-coup

An Aerobic and Very Fast Pd/C-Catalyzed Ligand-Free and Aqueous Suzuki Reaction Under Mild Conditions

Pd/C-catalyzed Suzuki reaction is a simple, efficient, and mild method for cross-coupling aryl bromides with arylboronic acids, yielding excellent yields within short reaction times.

A mild robust generic protocol for the Suzuki reaction using an air stable catalyst

This mild but robust generic protocol for the Suzuki-Miyaura reaction using an air stable palladium catalyst allows for complete conversion to biphenyls in less than 1 h, with sensitive functional groups and structural motifs well tolerated.

"Greening Up" the Suzuki Reaction

This rapid, green Suzuki reaction in water is suitable for both undergraduate and graduate students, exposing them to aqueous microscale organic reactivity and highlighting industrially applicable processes.

A novel synthesis of biaryl-containing macrocycles by a domino Miyaura arylboronate formation: intramolecular Suzuki reaction.

This novel macrocyclization procedure successfully synthesizes biaryl-containing macrocycles by combining Miyaura's arylboronic ester synthesis and intramolecular Suzuki reaction, with concentration being crucial for success.

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