224311-49-3Relevant articles and documents
The Use of Catalytic Amounts of CuCl and Other Improvements in the Benzyne Route to Biphenyl-Based Phosphine Ligands
Kaye, Steven,Fox, Joseph M.,Hicks, Frederick A.,Buchwald, Stephen L.
, p. 789 - 794 (2007/10/03)
Biphenyl-based phosphine ligands can be prepared on a significantly larger scale than previously possible as a result of the following discoveries and improvements to the original experimental procedure: the finding that CuCl catalyzes the coupling of hindered dialkylchlorophosphines with Grignard reagents; the development of conditions that permit ClPCy2 to be prepared and utilized in situ; the development of a more reliable large-scale preparation of 2-dimethylaminophenylmagnesium halide.
Novel electron-rich bulky phosphine ligands facilitate the palladium-catalyzed preparation of diaryl ethers
Aranyos, Attila,Old, David W.,Kiyomori, Ayumu,Wolfe, John P.,Sadighi, Joseph P.,Buchwald, Stephen L.
, p. 4369 - 4378 (2007/10/03)
A general method for the palladium-catalyzed formation of diaryl ethers is described. Electron-rich, bulky aryldialkylphosphine ligands, in which the two alkyl groups are either tert-butyl or 1-adamantyl, are the key to the success of the transformation. A wide range of electron-deficient, electronically neutral and electron-rich aryl bromides, chlorides, and triflates can be combined with a variety of phenols with the use of sodium hydride or potassium phosphate as base in toluene at 100 °C. The bulky yet basic nature of the phosphine ligand is thought to be responsible for increasing the rate of reductive elimination of the diaryl ether from palladium.
