33089-86-0Relevant articles and documents
Palladium/proazaphosphatrane-catalyzed amination of aryl halides possessing a phenol, alcohol, acetanilide, amide or an enolizable ketone functional group: Efficacy of lithium bis(trimethylsilyl)amide as the base
Urgaonkar, Sameer,Verkade, John G.
, p. 611 - 616 (2004)
A commercially available catalyst system comprising Pd(OAc)2 or Pd2(dba)3 and the proazaphosphatrane ancillary ligand P(i-BuNCH2CH2)3N (1) for the amination of aryl halides substituted with a phenol, alcohol, acetanilide, amide or ketone group containing an enolizable hydrogen is described. The reaction is performed in the presence of LiN(SiMe3)2 as the base. Other bases tested were either less effective or completely non-functional.
Polymer-supported copper complex for C-N and C-O cross-coupling reactions with aryl boronic acids
Chiang, Gary C. H.,Olsson, Thomas
, p. 3079 - 3082 (2007/10/03)
(Chemical Equation Presented) Immobilization of copper onto modified Wang resin provided a polymer-supported copper catalyst, which is effective in cross-coupling reactions between N- or O-containing substrates and arylboronic acids. The copper catalyst is air stable and can be recycled with minimal loss of activity.
Expanding Pd-catalyzed C-N bond-forming processes: The first amidation of aryl sulfonates, aqueous amination, and complementarity with Cu-catalyzed reactions
Huang, Xiaohua,Anderson, Kevin W.,Zim, Danilo,Jiang, Lei,Klapars, Artis,Buchwald, Stephen L.
, p. 6653 - 6655 (2007/10/03)
The first general method for the Pd-catalyzed amination of aryl tosylates and benzenesulfonates was developed utilizing ligand 1, which belongs to a new generation of biaryl monophosphine ligands. In addition, the new catalyst system for the first time enables amidation of aryl arenesulfonates and aqueous amination protocols that do not necessitate the use of cosolvents. The substrate scope has been significantly expanded to include aryl halides containing primary amides and free carboxylic acid groups. In the case of multifunctional substrates, the Pd-catalyzed amination can provide selectivity that is complementary to the Cu-catalyzed C-N bond-forming processes. Copyright