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Usage

InChI:InChI=1/C13H21N/c1-10(2)14(11(3)4)13-8-6-12(5)7-9-13/h6-11H,1-5H3

Upstream product

• 106-49-0 p-toluidine 
• 92197-18-7 N, N-diisopropyl-O-benzoyl hydroxylamine 
• 1234215-21-4 IMesCu-(4-Me)Ph 
• 108-18-9 diisopropylamine 
• 106-38-7 para-bromotoluene 
• 100705-30-4 1,4-dimethyl-7-p-tolyl-2,5-dithia-7-aza-bicyclo[2.2.1]heptane 
• 146511-93-5 2,5-dimethyl-[1,4]dithiane-2,5-diol 
• 29540-83-8 p-tolyl triflate 
• 32578-31-7 3-tolyl triflate 

Relevant academic research and scientific papers

Efficient catalytic aryl amination of bromoarenes using 3-iminophosphine palladium(II) chloride

While pursuing the development of new hydroamination catalysts, a 3-iminophosphine palladium(II) chloride complex [(3IP)PdCl2] was synthesized that has subsequently proven to be an effective precatalyst for the aryl amination of bromoarenes. This (3IP)PdCl2 complex has been utilized in the catalytic aryl amination of both bromobenzene and bromopyridine derivatives, specifically yielding excellent activity in coupling reactions involving bromobenzene, 4-bromotoluene, and 2-bromopyridine. Using a standard set of catalytic conditions, many alkyl and aryl amines have been investigated as coupling partners in the aryl amination of bromoarenes. In general, secondary alkyl amines and ortho-substituted anilines proved to be the best substrates for this reaction, commonly giving quantitative conversion to products, while primary amines and other anilines gave only poor to moderate results. Catalytic screening data, product yields, and full characterization of isolated products are included.

Synthesis of hindered anilines: Copper-catalyzed electrophilic amination of aryl boronic esters

No longer a hindrance: Copper-catalyzed electrophilic amination of aryl boronic esters is accomplished under mild reaction conditions using 2.5-5.0 mol % of a catalyst derived from copper tert-butoxide and Xantphos ligand (see scheme). The reaction tolerates a wide range of functional groups and can be used to prepare some of the most hindered anilines made to date. Copyright

The anionic thia-Fries rearrangement of aryl triflates

Aryl triflates undergo LDA-mediated rearrangement to generate o-hydroxyaryl trifluoromethylsulfones. In some cases, partitioning between rearrangement and aryne generation can be controlled.

Benzyne Generation from Aryl Triflates

The use of aryl triflates to form arynes as reactive intermediates is decribed.This allows the first general use of phenols as aryne precursors.Phenyl triflate reacts with LDA at -78 deg C to form benzyne, which then reacts with diisopropylamine generating N,N-diisopropylaniline.Yields of diisopropylarylamines from aryne intermediates are superior to those previously reported.Regioisomeric ratios are similar to those obtained with use of other benzyne precursors.