20841-05-8

Upstream product

• 104-94-9 4-methoxy-aniline 
• 996-50-9 N,N-diethyl-1,1,1-trimethylsilanamine 
• 75-77-4 chloro-trimethyl-silane 
• 501-58-6 (E)-1,2-bis(4-methoxyphenyl)diazene 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 4039-32-1 lithium hexamethyldisilazane 
• 623-12-1 4-chloromethoxybenzene 
• 696-62-8 para-iodoanisole 
• 71-43-2 benzene 

Downstream Products

• 104-94-9 4-methoxy-aniline 

Relevant academic research and scientific papers

Direct arylation of benzene with aryl bromides using high-temperature/high- pressure process windows: Expanding the scope of c-h activation chemistry

A detailed investigation on the direct arylation of benzene with aryl bromides by using first-row transition metals under high-temperature/high- pressure (high-T/p) conditions is described. By employing a parallel reactor platform for rapid reaction screening and discovery at elevated temperatures, various metal/ligand/base combinations were evaluated for their ability to enable biaryl formation through C-H activation. The combination of cobalt(III) acetylacetonate and lithium bis(trimethylsilyl)amide was subjected to further process intensification at 200°C (15 bar), allowing a significant reduction of the catalyst/base loading and a dramatic increase in catalytic efficiency (turnover frequency) by a factor of 1000 compared to traditional protocols. The high-throughput screening additionally identified novel nickel-and copper-based metal/ligand combinations that favored an amination pathway competing with C-H activation, with the addition of ligands, such as 1,10-phenanthroline, having a profound influence on the selectivity. In addition to metal-based catalysts, high-T/p process windows were also successfully applied to transition-metal-free systems, utilizing 1,10-phenanthroline as organocatalyst. Copyright

General preparation of primary, secondary, and tertiary aryl amines by the oxidative coupling of polyfunctional aryl and heteroaryl amidocuprates

(Chemical Equation Presented). A tolerant reaction: Functionalized tertiary amines have been prepared by the oxidative coupling of amidocuprates with chloranil used as the oxidant (see Scheme). A high tolerance of functional groups and insensitivity to steric hindrance characterize this general amination reaction.

Palladium-catalyzed synthesis of arylamines from aryl halides and lithium bis(trimethylsilyl)amide as an ammonia equivalent

(Equation presented) A simple, palladium-catalyzed method to convert aryl halides to the parent anilines using lithium bis(trimethylsilyl)amide (LiN(SiMe3)2) is reported. The reaction is catalyzed by Pd(dba)2 and P(t-Bu)3 and can be run with as little as 0.2 mol % of catalyst. The reaction is faster than competing generation of benzyne intermediates and, therefore, provides the aniline products regiospecifically.

Novel Syntheses of Bis(trialkylsilyl)amines by Reductive Trialkylsilylation of Azo Compounds

Reduction of azo compounds with a system of a trialkylchlorosilane and lithium has been found to afford bis(trialkylsilyl)amines in the presence of a transition metal halide as a catalyst in THF.The reaction course was significantly modified by using t-butyldimethylchlorosilane as a trialkylchlorosilane.