Abstract
AbstractThe gold‐catalyzed mono‐hydroarylation and two‐fold hydroarylation of alkynes with electron‐rich heteroarenes was analyzed by a 1H NMR kinetic study. The obtained rate constants for the decreasing alkyne concentration provide information on the reactivity of this addition reaction. The examinations show the orthogonal reactivity of gold and a proton for the two reaction steps. The first hydroarylation is exclusively promoted by gold(I), whereas the second step is premised on a proton which will be reversibly derived from the formation of σ,π‐acetylide complexes from the terminal alkynes or by interaction with solvents. Based on kinetic data, it was possible to synthesize a large range of mono‐adducts in moderate to good yields, furthermore the synthesis of hetero‐di‐adducts, bearing two different substituents, was explored.magnified image
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