Palladium-Catalyzed Suzuki-Miyaura Cross-coupling Reactions Employing Dialkylbiaryl Phosphine Ligands

Palladium-Catalyzed Suzuki-Miyaura Cross-coupling Reactions Employing Dialkylbiaryl Phosphine Ligands

2008 November 18; 41(11): 1461–1473 | Ruben Martin and Stephen L. Buchwald
The article discusses the use of dialkylbiaryl phosphine ligands in palladium-catalyzed Suzuki-Miyaura (SMC) cross-coupling reactions, which are crucial for synthesizing biaryl and substituted aromatic structures. These ligands, introduced in 1998, have significantly enhanced the efficiency and selectivity of SMC reactions by improving the rates of oxidative addition, transmetallation, and reductive elimination. The authors highlight the broad applicability of these ligands, which can be used with a wide range of substrates, including aryl bromides, aryl triflates, unactivated aryl chlorides, aryl tosylates, heteroaryl systems, and very hindered substrate combinations. The ligands are also noted for their stability, ease of handling, and the ability to work at mild conditions, making them valuable tools in organic synthesis. The article provides an overview of the mechanistic framework behind these reactions and discusses selected applications in the synthesis of natural products and new materials, demonstrating the utility of dialkylbiarylphosphine ligands in various synthetic contexts.The article discusses the use of dialkylbiaryl phosphine ligands in palladium-catalyzed Suzuki-Miyaura (SMC) cross-coupling reactions, which are crucial for synthesizing biaryl and substituted aromatic structures. These ligands, introduced in 1998, have significantly enhanced the efficiency and selectivity of SMC reactions by improving the rates of oxidative addition, transmetallation, and reductive elimination. The authors highlight the broad applicability of these ligands, which can be used with a wide range of substrates, including aryl bromides, aryl triflates, unactivated aryl chlorides, aryl tosylates, heteroaryl systems, and very hindered substrate combinations. The ligands are also noted for their stability, ease of handling, and the ability to work at mild conditions, making them valuable tools in organic synthesis. The article provides an overview of the mechanistic framework behind these reactions and discusses selected applications in the synthesis of natural products and new materials, demonstrating the utility of dialkylbiarylphosphine ligands in various synthetic contexts.
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[slides] Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions employing dialkylbiaryl phosphine ligands. | StudySpace