Substitution reactions using organocopper

Stilbenes, photocyclization of, 30, 1 StiUe reaction, 50, 1 Stobbe condensation, 6, 1 Substitution reactions using organocopper reagents, 22, 2 41, 2 Sugars, synthesis by glycosylation with sulfoxides and sulfinates, 64, 2 Sulfide reduction of nitroarenes, 20, 4 Sulfonation of aromatic hydrocarbons and aryl halides, 3, 4 Swem oxidation, 39, 3 53, 1... 

G. H. Posner, Substitution Reactions Using Organocopper Reagents, Org. React. 1975, 22, 253-400. 

Substitution Reactions Using Organocopper Reagents Gary H. Posner... 

Sn2 substitution using organocopper reagents is an efficient method for the synthesis of 3-substituted olefins. In the synthesis of farnesyl diphosphate analogues (43, 45) as potential inhibitors of the enzyme protein-farnesyl transferase, for example, organocopper methodology was compared with the Stifle reaction [33] and the Suzuki reaction [34], frequently used in the coupling of vinyl triflates with... 

Sn2 substitution reactions of alkyl halides with hard nucleophiles such as alkyl anions can be achieved most readily with the aid of organocopper chemistry [95]. Sn2 reactions with epoxides and aziridines are also synthetically useful [96]. The... 

Therefore, the isomerization reaction was also performed starting from the a-substituted enol ether 119 (Scheme 52). By using the tandem allylic C-H activation-elimination reactions, Z-120c is initially formed and by a transmetalation reaction into organocopper with a stoichiometric amount of CuCI/ 2LiCl, followed by heating at +50 °C for 1 h and reaction with allyl chloride, the resulting ( , )-diene 122 is obtained with an isomeric ratio of 90 10 but in a low 40% yield as described in Scheme 52. 

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