33089-86-0

Upstream product

• 103-88-8 4-bromoacetanilide 
• 106-49-0 p-toluidine 
• 106-38-7 para-bromotoluene 
• 122-80-5 N-acetyl-p-phenylenediamine 
• 539-03-7 N-(4-chlorophenyl)acetamide 
• 5720-05-8 4-methylphenylboronic acid 
• 3076-56-0 p-tolyllead triacetate 

Relevant academic research and scientific papers

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

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.

Pd-catalyzed amination in a polar medium: Rate enhancement, convenient product isolation, and tandem Suzuki cross-coupling

A catalytic system utilizing a polar medium for the Pd-catalyzed amination reaction is described. This system utilizes Pd[P(t-Bu)3]2 and a weak base and displays a modest rate enhancement compared to similar existing protocols. Significant functional group tolerance is observed in both amine and aryl halide, including carboxylates, carbamates, nitriles, amides, and esters. Product isolation after filtration and automated reverse-phase chromatography readily permits parallel synthetic approaches if desired.

Ligands for metals and improved metal-catalyzed processes based thereon

One aspect of the present invention relates to ligands for transition metals. A second aspect of the present invention relates to the use of catalysts comprising these ligands in transition metal-catalyzed carbon-heteroatom and carbon-carbon bond-forming reactions. The subject methods provide improvements in many features of the transition metal-catalyzed reactions, including the range of suitable substrates, reaction conditions, and efficiency.

Polymer-supported copper complex for C-N and C-O cross-coupling reactions with aryl boronic acids

(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

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

Improved functional group compatibility in the palladium-catalyzed synthesis of aryl amines

(figure presented) The use of Pd2dba3 with bulky, electron-rich ligands 1 or 2 and LiN(TMS)2 as the base for the coupling of amines with aryl halides containing hydroxyl, amide, or enolizable keto groups is described. This protocol expands the utility of palladium-catalyzed C-N bond formation by allowing for the use of aryl halides containing these functional groups, obviating the need for protecting group manipulations.

Copper-catalyzed coupling of arylboronic acids and amines.

[reaction: see text] A general catalytic coupling of arylboronic acids and amines is reported. This room-temperature coupling was realized through the use of catalytic copper(II) acetate, 2,6-lutidine as base, and myristic acid as an additive. Functionalized aniline substrates provided the diarylamine coupling products in good yield (58-91%). A variety of alkylamines were also successfully coupled to give N-alkyl anilines in moderate yield (50-64%).

New synthetic applications of aryllead triacetates. N-arylation of amides

p-Tolyllead triacetate efficiently arylates the nitrogen atom of carboxamide, sulfonamide, imide, and hydantoin anions under mild conditions. This reaction did not interfere with the arylation of amino and β-dicarbonyl groups.