53370-98-2

Upstream product

• 118761-71-0 C₁₀H₁₄ClN 
• 122-00-9 para-methylacetophenone 
• 74-89-5 methylamine 
• 622-97-9 1-ethenyl-4-methylbenzene 

Downstream Products

• 42071-14-7 methyl-(1-p-tolyl-ethyl)-amine 
• 1156547-00-0 C₁₀H₁₅N 
• 1227083-40-0 1,3-dimethyl-1-phenyl-3-(1-p-tolylvinyl)urea 

Relevant academic research and scientific papers

Photocatalytic Difunctionalization of Vinyl Ureas by Radical Addition Polar Truce–Smiles Rearrangement Cascades

We report tandem alkyl-arylations and phosphonyl-arylations of vinyl ureas by way of a photocatalytic radical-polar crossover mechanism. Addition of photoredox-generated radicals to the alkene forms a new C?C or C?P bond and generates a product radical adjacent to the urea function. Reductive termination of the photocatalytic cycle generates an anion that undergoes a polar Truce–Smiles rearrangement, forming a C?C bond. The reaction is successful with a range of α-fluorinated alkyl sodium sulfinate salts and diarylphosphine oxides as radical precursors, and the conformationally accelerated Truce–Smiles rearrangement is not restricted by the electronic nature of the migrating aromatic ring. Formally the reaction constitutes an α,β-difuctionalisation of a carbon–carbon double bond, and proceeds under mild conditions with visible light and a readily available organic photocatalyst. The products are α,α-diaryl alkylureas typically functionalized with F or P substituents that may be readily converted into α,α-diaryl alkylamines.

Tackling N-Alkyl Imines with 3d Metal Catalysis: Highly Enantioselective Iron-Catalyzed Synthesis of α-Chiral Amines

A readily activated iron alkyl precatalyst effectively catalyzes the highly enantioselective hydroboration of N-alkyl imines. Employing a chiral bis(oxazolinylmethylidene)isoindoline pincer ligand, the asymmetric reduction of various acyclic N-alkyl imines provided the corresponding α-chiral amines in excellent yields and with up to >99 % ee. The applicability of this base metal catalytic system was further demonstrated with the synthesis of the pharmaceuticals Fendiline and Tecalcet.

Cooperative Lewis Acid/Cp?CoIII Catalyzed C-H Bond Activation for the Synthesis of Isoquinolin-3-ones

A facile route toward the synthesis of isoquinolin-3-ones through a cooperative B(C6F5)3- and Cp?CoIII-catalyzed C-H bond activation of imines with diazo compounds is presented. The inclusion of a catalytic amount of B(C6F5)3 results in a highly efficient reaction, thus enabling unstable NH imines to serve as substrates. CoIII-operative catalysis: The first facile route toward the synthesis of isoquinolin-3-ones through cooperative C-H bond activation with B(C6F5)3 (BCF in picture) and Cp?CoIII (Cp?=C5Me5) is presented. The newly developed catalytic system is highly reactive, thus unstable NH imines can serve as substrates.

Iron catalysed nitrosation of olefins to oximes

Fe(BF4)2·6H2O/2,6- pyridinedicarboxylic acid catalysed nitrosation of a wide variety of substituted styrenes has been developed in the presence of t-BuONO/NaBH4 under H2 pressure (10 bar) in MeOH-H2O (5 : 1) to afford corresponding oximes in good to excellent yields.

Geometry-selective synthesis of e or Z N -vinyl ureas (N -carbamoyl enamines)

N-Vinyl ureas are emerging as a valuable class of compounds with both nucleophilic and electrophilic reactivity. They may be made by capturing the enamine tautomer of an imine with an isocyanate, a reaction which in general leads to the E isomer of the vi

Tandem β-alkylation-α-arylation of amines by carbolithiation and rearrangement of N -carbamoyl enamines (Vinyl Ureas)

Organolithiums add in an umpolung fashion to the β-carbon of N-carbamoyl enamines (N-vinyl ureas). The reaction proceeds with syn diastereospecificity and provides urea-stabilized, configurationally defined organolithiums. Facilitated by coordinating solv

Reactions of N-Halo-N-methylbenzylamines with MeONa-MeOH and t-BuOK-t-BuOH. Effects of β-Carbon Substituent and Base-Solvent System upon the Imine-Forming Transition State

Elimination reactions of YC6H4CH(R)N(X)CH3 in which R = Me and Ph and X = Cl and Br promoted by MeONa-MeOH and t-BuOK-t-BuOH have been studied kinetically.The elimination reactions are regiospecific, producing only the corresponding N-benzylidenemethylami