Hydrogenation Catalysed by Palladium or Rhodium Chlorides in the Presence of TDA-1

Tris[2-(2-methoxyethoxy)ethyl]amine

“…The methodology was extended to displacements by potassium methoxide on fluorobenzene and 1-fluoronaphthalene, and by potassium tert-butoxide on bromobenzene in yields ranging from 64-93%. Estrone triflate (28), when subjected to potassium thioacetate and TDA-1 in toluene at room temperature, gave 29 in 56% yield (eq 10). 12 Finally, aryl fluorides and chlorides bearing an electron-withdrawing group undergo the S N Ar reaction with trifluoroethanol at elevated temperatures (100-147 • C) in the presence of NaOH and 5-10 mol % TDA-1 to give the corresponding trifluoroethyl ethers (36-82% yield).…”