251320-86-2Relevant articles and documents
An efficient and safe procedure for the large-scale Pd-catalyzed hydrazonation of aromatic chlorides using buchwald technology
Mauger, Christelle C.,Mignani, Gerard A.
, p. 1065 - 1071 (2004)
A convenient, optimized and safe synthesis of N-arylhydrazines, useful as intermediates for active ingredients in agricultural and pharmaceutical applications, is reported. Starting from aryl halides (chlorides and bromides), a palladium-catalyzed carbon-nitrogen coupling reaction followed by an acidic treatment afforded the target molecules in good to excellent yields using low catalyst loadings. This technology has then been successfully applied on a large scale in a pilot plant. This contribution also describes the major improvements in ligand synthesis and the thermal data required to develop a process on a pilot scale.
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.
Highly active palladium catalysts for Suzuki coupling reactions
Wolfe, John P.,Singer, Robert A.,Yang, Bryant H.,Buchwald, Stephen L.
, p. 9550 - 9561 (2007/10/03)
Mixtures of palladium acetate and o-(di-tert-butylphosphino)biphenyl (4) catalyze the room-temperature Suzuki coupling of aryl bromides and aryl chlorides with 0.5-1.0 mol % Pd. Use of o-(dicyclohexylphosphino)biphenyl (2) allows Suzuki couplings to be carried out at low catalyst loadings (0.000001-0.02 mol % Pd). The process tolerates a broad range of functional groups and substrate combinations including the use of sterically hindered substrates. This is the most active catalyst system in terms of reaction temperature, turnover number, and steric tolerance which has been reported to date.
