861-67-6

Upstream product

• 76-84-6 triphenylmethyl alcohol 
• 4083-64-1 Tosyl isocyanate 
• 519-73-3 triphenylmethane 
• 127-65-1 chloroamine-T 
• 55962-05-5 [N-(p-tolylsulfonyl)imino]phenyliodinane 
• 41085-71-6 bromamine T 
• 596-43-0 bromo-triphenyl-methane 
• 14309-25-2 trityl azide 
• 5824-40-8 Triphenylmethylamin 
• 4104-47-6 N-sulfinyl-p-toluenesulfonamide 

Relevant academic research and scientific papers

Visible-light-mediated, nitrogen-centered radical amination of tertiary alkyl halides under metal-free conditions to form α-tertiary amines

A mild and operationally convenient amino-functionalization of a range of tertiary alkyl halides by reaction with iminoiodinanes (PhINNs) and I2 has been developed. According to the mechanistic experiments described within, the reaction is spec

Iron-catalyzed efficient intermolecular amination of C(sp3)-H bonds with bromamine-T as nitrene source

[Fe(N4Py)(CH3CN)](ClO4)2 can efficiently catalyze intermolecular nitrene insertion of sp3 C-H bonds with bromamine-T as the nitrene source, forming the desired tosylprotected amines with NaBr as the by-product.

A versatile tripodal Cu(I) reagent for C-N bond construction via nitrene-transfer chemistry: Catalytic perspectives and mechanistic insights on C-H aminations/amidinations and olefin aziridinations

A CuI catalyst (1), supported by a framework of strongly basic guanidinato moieties, mediates nitrene-transfer from PhI=NR sources to a wide variety of aliphatic hydrocarbons (C-H amination or amidination in the presence of nitriles) and olefins (aziridination). Product profiles are consistent with a stepwise rather than concerted C-N bond formation. Mechanistic investigations with the aid of Hammett plots, kinetic isotope effects, labeled stereochemical probes, and radical traps and clocks allow us to conclude that carboradical intermediates play a major role and are generated by hydrogen-atom abstraction from substrate C-H bonds or initial nitrene-addition to one of the olefinic carbons. Subsequent processes include solvent-caged radical recombination to afford the major amination and aziridination products but also one-electron oxidation of diffusively free carboradicals to generate amidination products due to carbocation participation. Analyses of metal- and ligand-centered events by variable temperature electrospray mass spectrometry, cyclic voltammetry, and electron paramagnetic resonance spectroscopy, coupled with computational studies, indicate that an active, but still elusive, copper-nitrene (S = 1) intermediate initially abstracts a hydrogen atom from, or adds nitrene to, C-H and C=C bonds, respectively, followed by a spin flip and radical rebound to afford intra- and intermolecular C-N containing products.

Ligand-assisted, copper-catalyzed enantioselective benzylic amination

Several classes of ligands, including α-amino acids, diamines, diphosphines, bis-oxazolines, and diimines, support efficient copper-catalyzed amination of benzylic hydrocarbons by anhydrous chloramine-T. Catalysts derived from homochiral ligands, particularly chiral diimines, effect aminosulfonation with low to moderate enantioselectivity.

Hydrous zinc halide-catalyzed aminosulfonation of hydrocarbons

Benzylic and allylic hydrocarbons are selectively converted to the corresponding sulfonamides by a ZnBr2-H2O-catalyzed reaction with PhI=NTs; saturated adamantane is aminosulfonated at the tertiary C-H bond. The Royal Society of Chemistry.

Efficient copper-catalyzed benzylic amidation with anhydrous chloramine-T

Benzylic hydrocarbons are selectively converted to the corresponding sulfonamides by the [Cu(CH3CN)4]PF6-catalyzed reaction with anhydrous TolSO2NNaCl (chloramine-T). Under the same conditions, representative ethers are also α-amidated; olefins produce allyl sulfonamides, aziridines, and/or β-chloro sulfonamides.

A CHEMOSELECTIVE CONVERSION OF ALKYL AND ARYL AZIDES TO AMINES WITH SODIUM HYDROGENTELLURIDE

By treatment with sodium hydrogentelluride in ethanol/ether at room temperature, alkyl and aryl azides are easily converted to the corresponding primary amines in good yields.

REACTIONS OF N-SULFINYL-p-TOLUENESULFONAMIDE WITH ALCOHOLS

N-Sulfinyl-p-toluenesulfonamide (1) reacted with triaryl- and diarylmethanols to give predominantly N-substituted sulfonamides and SO2 presumably via carbonium ion intermediates.When carbonium ion forming alcohols, such as t-BuOH and Ph2C(Me)OH, were used, the predominant products were alkenes and p-toluenesulfonamide.Allylic alcohols afforded N-substituted sulfonamides, along with dienes and p-toluenesulfonamide.Alcohols wich could not predictably give relatively stable intermediate carbonium ions, gave either dialkyl sulfites or dialkyl ethers, along with p-toluenesulfonamide.In one case, namely with 9-phenylfluorenol, the 1:1 adduct with 1 (an amidosulfite) was isolated.A mechanism for the reaction is proposed.