A novel method for (Z)-stereoselective preparation of CF3-substituted enediynes and their coupling reactions

Ag-Mediated Reactions: Coupling and Heterocyclization Reactions

“…71 Jeong et al also applied the same conditions to coupling reactionsofbis(trimethylsilyl)enediynesandaffordedbis(aryl)enediynes. 72 Interestingly, a recent report broadened the scope of such couplings. Wu et al showed that aryl boronic acids as well as boronates could be engaged in coupling reactions with terminal alkynes in the presence of a palladacycle as catalyst and silver oxide.…”

Mild and Copper‐Free Stereoselective Cyanation of gem‐Difluoroalkenes by Using Benzyl Nitrile as a Cyanating Reagent

“…Eur.J.2016, 22,9902 -9908 www.chemeurj.org mediate IV would form two conformational intermediates, VI and VIII.T he more stable intermediate VI wase asily generated because there might be no electronic repulsionb etween fluorine atom and aryl group. [29] Finally,t he elimination of LiF from the intermediate VI with the assistanceo ftBuOLi furnished fluorinated alkenyl nitrile with an excellent E selectivity.…”

Coupling Reactions Promoted by Silver

“…133 Under essentially the same conditions, Jeong et al were able to prepare disubstituted trifluoromethylated enediynes, either directly through a dicoupling reaction from bis(trimethylsilyl)enediynes or through successive couplings from mono(trimethyl silyl)enediynes (Scheme 10.82). 134 The first direct coupling of terminal alkynes with aryl iodides or bromides without palladium was reported by Wang and Li in 2006. 135 Silver iodide and triphenylphosphane in polar solvents proved to be the best catalyst combination, while potassium carbonate proved to be the better base, giving diarylacetylenes in high yields ( …”