Recent Applications of Phosphane-based Palladium Catalysts in Suzuki-Miyaura Reactions Involved in Total Syntheses of Natural Products

Abstract

This review with 800 references illustrates applications of Suzuki-Miyaura (S.-M.) reactions in the total syntheses of 147 natural products that were made in the period 2010–2013. The review has been organized on the basis of the seven classes of phosphane-based Pd catalysts that have been used in the reported total syntheses. Emphasis has been given to describe and discuss the experimental conditions of the Pd-catalyzed (S.-M.) cross-coupling reactions also outlining the methods used to prepare the reactants. A focus has also been set on the biological and pharmacological properties of the reported natural products as well as on the most significant steps of the reported total syntheses

Chemistry informer libraries: a chemoinformatics enabled approach to evaluate and advance synthetic methods

“…3D , entry 1). Subsequently, we tested (1,1′-bis(diphenylphosphino)ferrocene)palladium( ii )chloride [(dppf)PdCl 2 ] under similar conditions and found that this bidentate phosphine palladium catalyst that has found extensive application in natural product and drug synthesis 16 gave successful outcomes with all 24 members and a higher overall average yield (entry 2). 17 Despite their strengths, both of these catalysts exhibit limited scope with aryl chloride substrates.…”

We Already Know Everything about Oxidative Addition to Pd(0): Do We?

“…Amines and nitrogen-containing heteroarenes are widely used in cross-coupling reactions, either as substrates in Buchwald–Hartwig aminations , and in C–H activation reactions or as bases as in the case of the Suzuki–Miyaura and Sonogashira cross-couplings or as ligands. Additionally, primary and secondary amines can also play the role of reducing agents to generate Pd(0) from the Pd­(II) precatalyst. ,,,, …”

Current Applications of Suzuki–Miyaura Coupling Reaction in The Total Synthesis of Natural Products: An update

“…After this outstanding accomplishment, asymmetric SMCR has been frequently employed in the total synthesis of several other natural products such as steganone as well as for the construction of most chiral biaryl systems present as scaffolds in naturally occurring compounds . The impact of asymmetric SMCR in total synthesis is increasing exponentially as evidenced by recent reviews represented in the chemical literature …”