And Sonogashira coupling

A silver(i) complex having the heterosubstituted 3-methyl-l-(2-pyridylmethyl)imidazol-2-ylidene ligand, [Ag(carbene)2] [I/Agl2] 37, was reported, which was further reacted to give a series of palladium(n) carbene complexes that were demonstrated to be active catalysts toward Heck, Suzuki, and Sonogashira coupling reactions.87... 

Aryl-acetylene synthesis, Cf. Cadiot-Chodkiewicz coupling and Sonogashira coupling. The Castro-Stephens coupling uses stoichiometric copper, whereas the Sonogashira variant uses catalytic palladium and copper. 

Corma A, Garcfa H, Leyva A (2005) Comparison between polyethylenglycol and imidazolium ionic liquids as solvents for developing a homogeneous and reusable palladium catalytic system for the Suzuki and Sonogashira coupling. Tetrahedron 61(41) 9848-9854... 

Tzschucke, C.C., Marker , C., Glatz, H., and Bannwarth, W. 2002. Fluorous biphasic catalysis without perfluorinated solvents Application to Pd-mediated Suzuki and Sonogashira couplings. Angewandte Chemie International Edition, 41 4500-03. 

Triflates of 3-benzo[. ]furans were prepared, and evaluated in the palladium-catalyzed Stille, Heck, Suzuki, and Sonogashira coupling reactions. As can be seen in Scheme 55, results demonstrated that benzo[. ]furan-3-triflate 109 was a good coupling partner in the metal-catalyzed reactions, and good to excellent results were obtained <2002SL501>. 

Suzuki, Stille, Kumada, Hiyama and Sonogashira couplings... 

E.I2Z)-10.12-hexadecadienal CHO Melon worm Diaphtinia hyalimila) Fs Palladium-catalyzed coupling and Sonogashira coupling [153]... 

Intramolecular iminoacetonitrile [4-1-2] cycloaddition has been exploited in the synthesis of quinolizidine alkaloids (Scheme 54). The intermediate 187 was generated by elimination of trifluoromethanesulfinate from 188 and underwent the desired aza Diels-Alder reaction to give 189. A series of steps which included reduetive decyanation, alkylation with (Z)-3-bromo-l-chloropropene, classical resolution, and Sonogashira coupling provided the alkaloid (-)-217A 190<050L3115>. 

Other biphasic C—C bonding reactions were carried out with fluorous solvents, for instance Suzuki- and Sonogashira-couplings [124] or ethene or propene oligomerizations [125, 126], Further new solvent systems use ionic liquids for the linear dimerisation of 1-butene to octenes [127] or the hydrovinylation of styrene with a combination ionic liquid/supercritical carbon dioxide [128] (cf. Section 7.4). 

Nonpolar biphasic catalysis Suzuki- and Sonogashira coupling reactions... 

NONPOLAR BIPHASIC CATALYSIS SUZUKI- AND SONOGASHIRA COUPLING REACTIONS... 

Palladium catalyst supported on poly(4-methylstyrene) can be used for biphasic nonpolar Suzuki and Sonogashira coupling of aryl bromides and chlorides with good product yields. The catalyst can be recycled five times with negligible decrease in the activity. 

Thiolactams enter Suzuki coupling and Sonogashira coupling with loss of the sulfur atom when copper(I) 2-thienylcarboxylate is also present. 

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