s, or keywords if they used Heck-type chemistry in their syntheses, because it became one of basic tools of organic preparations, a natural way to

http://aether.cmi.ua.ac.be/artikels/Artikels%20Gitte/Artikels/Reviews/Heck%20reactie%20Beletskaya%20%20Chem.%20Rev.%20003009.pdf

The heck reaction as a sharpening stone of palladium catalysis.

/pdf/aryl-aryl-bond-formation-one-century-after-the-discovery-of-1jdyxlkwix.pdf

Aryl-aryl bond formation one century after the discovery of the Ullmann reaction.

Selected patented cross-coupling reaction technologies.

Dialkylbiaryl phosphines are a valuable class of ligand for Pd-catalyzed amination reactions and have been applied in a range of contexts. This perspective attempts to aid the reader in the selection of the best choice of reaction conditions and ligand of this class for the most commonly encountered and practically important substrate combinations.

/pdf/dialkylbiaryl-phosphines-in-pd-catalyzed-amination-a-user-s-54l9jb3w9l.pdf

Dialkylbiaryl Phosphines in Pd-Catalyzed Amination: A User's Guide.

phinoethane) seemed mainly to stabilize intermediates, and often the catalytic reactions were slower when dppe was used instead of the most common monodentate triphenylphosphine. We will briefly review the history of “ligand effects” in catalysis before discussing a range of reactions for which a notable effect has been observed. It has taken quite some time before the positive effect that bidentates can have on selectivities and rates of catalytic reactions was fully recognized. Most of the established examples of bite angle effects involve diphosphine ligands. Therefore, many important catalysts containing a chelate ligand such as bipyridine and diimine will fall outside the scope of this review. The connecting bridge in these bidentates does play a dominant role in the performance of these catalysts, but systematic studies have not been published. The effects of phosphine ligands in catalysis have been known for quite some time. One of the first reports involves the use of triphenylphosphine in the “Reppe” chemistry, the reactions of alkynes, alcohols, and carbon monoxide.1 It was found that formation of acrylic esters was much more efficient using NiBr2(PPh3)2 than NiBr2 without ligand. In the commercial system, though, a phosphine-free catalyst is used. While the reaction was not yet understood mechanistically, the use of phosphines in catalysis attracted the attention of the petrochemical industry worldwide. An early example of a phosphine ligand modified catalytic process is the Shell process for alkene hydroformylation using a cobalt catalyst containing a trialkylphoshine.2 The reaction requires higher temperatures, but it leads to more linear product as compared to the unmodified catalyst. The general mechanism of the hydroformylation reaction has been known for a long time.3 Hydrocyanation as used by Du Pont is another early example of an industrially applied catalytic reaction employing ligands.4 It is a nickel-catalyzed reaction in which aryl phosphite ligands are used for the production of adiponitrile. The development of this process has played a key role in the introduction of the now very common study of “ligand effects” in the field of homogeneous catalysis by organometallic complexes.5 While several industries were working on new homogeneous catalysts, important contributions to the new field were made in academia in the early 1960s with the appearance of the first phosphinemodified hydrogenation catalysts. An early example of a phosphine-free ruthenium catalyst was published by Halpern.6 Triphenylphosphine-modified platinumtin catalysts for the hydrogenation of alkenes were reported by Cramer from Du Pont in 1963.7 In the same year Breslow (Hercules) included a few phosFigure 1. Bite angle: The ligand-metal-ligand angle of bidentate ligands. 2741 Chem. Rev. 2000, 100, 2741−2769

Ligand Bite Angle Effects in Metal-catalyzed C−C Bond Formation

Whereas the direct reduction of aryl triflates affords mainly phenols and some arenes, the presence of a catalytic amount of palladium or nickel results in the formation of biaryls. The homocoupling is performed in the presence of an electron source, either a cathode or zinc powder. A judicious choice of the metal (nickel or palladium), the ligand (monodentate or bidentate phosphine), and the reduction process (electrochemical or chemical) allows the synthesis of functional symmetrical biaryls. Nickel and palladium complexes ligated by bidentate ligands such as NiCl(2)(dppf) and Pd(OAc)(2) + 1 BINAP are very efficient for the homocoupling of 1-naphthyl triflate, since the dimer was obtained in almost quantitative yield. However, the homocoupling is sensitive to steric hindrance, excluding for the moment the synthesis of atropisomers. The homocoupling proceeds via an activation of the C-O bond of the aryl triflate by a palladium(0) (or a nickel(0)) complex, providing an intermediate arylpalladium(II) (or nickel(II)) complex that after activation by electron transfer affords a new complex able to undergo a second oxidative addition with the aryl triflates.

Nickel- and Palladium-Catalyzed Homocoupling of Aryl Triflates. Scope, Limitation, and Mechanistic Aspects.

The palladium(II) complex [PdCl2(PPh3)2] catalyses the electrosynthesis of biaryls from aryl triflates whereas, in the presence of carbon dioxide, this complex catalyses the electrosynthesis of aromatic carboxylic acids.

Palladium catalysed electrosynthesis using aryl trifluoromethanesulfonates (triflates). Synthesis of biaryls and aromatic carboxylic acids

Palladium and Nickel Catalyzed Synthesis of Biaryls from Aryl Triflates in the Presence of Zinc Powder

Palladium- and Nickel-Catalyzed Synthesis of Biaryls from Aryl Triflates in the Presence of Zinc Powder.

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Papers

Nickel- and Palladium-Catalyzed Homocoupling of Aryl Triflates. Scope, Limitation, and Mechanistic Aspects.

Palladium catalysed electrosynthesis using aryl trifluoromethanesulfonates (triflates). Synthesis of biaryls and aromatic carboxylic acids

Palladium and Nickel Catalyzed Synthesis of Biaryls from Aryl Triflates in the Presence of Zinc Powder

Palladium- and Nickel-Catalyzed Synthesis of Biaryls from Aryl Triflates in the Presence of Zinc Powder.

Nickel- and Palladium-Catalyzed Homocoupling of Aryl Triflates. Scope, Limitation, and Mechanistic Aspects.