Heck and Cross-Coupling Reactions: Two Core Chemistries in Metal-Catalyzed Organic Syntheses

Anionic Pd(0) and Pd(II) intermediates in palladium-catalyzed Heck and cross-coupling reactions.

The anions of PdCl(2)L(2) and Pd(OAc)(2), precursors of palladium(0) used in cross-coupling and Heck reactions, play a crucial role in these reactions. Tricoordinated anionic complexes Pd(0)L(2)Cl(-) and Pd(0)L(2)(OAc)(-) are the effective catalysts instead of the usually postulated Pd(0)L(2) complex. The anion ligated to the palladium(0) affects the kinetics of the oxidative addition to ArI as...

Palladium-Catalyzed Cross-Coupling Reactions of Perfluoro Organic Compounds

In this review, we summarize our recent development of palladium(0)-catalyzed cross-coupling reactions of perfluoro organic compounds with organometallic reagents. The oxidative addition of a C–F bond of tetrafluoroethylene (TFE) to palladium(0) was promoted by the addition of lithium iodide, affording a trifluorovinyl palladium(II) iodide. Based on this finding, the first palladium-catalyzed c...

The Metal-Catalyzed Cross-Coupling Reactions of n-Butylketene Dimer

Iron-catalyzed cross-coupling reactions.

Simple iron salts such as FeCl(n), Fe(acac)(n) (n = 2,3) or the salen complex 4 turned out to be highly efficient, cheap, toxicologically benign, and environmentally friendly precatalysts for a host of cross-coupling reactions of alkyl or aryl Grignard reagents, zincates, or organomanganese species with aryl and heteroaryl chlorides, triflates, and even tosylates. An "inorganic Grignard reagent...

Recent advances in noble metal nanocatalysts for Suzuki and Heck cross-coupling reactions.

Since metal nanoparticles have a high surface-to-volume ratio and very active surface atoms, they are very attractive catalysts for a wide variety of organic and inorganic reactions, compared to bulk catalysts. Metal nanoparticles suspended in colloidal solutions and those adsorbed onto bulk supports have been used as catalysts for a wide variety of carbon-carbon bond formation reactions such a...