16955-25-2

Upstream product

• 106-49-0 p-toluidine 

Downstream Products

• 16954-38-4 toluene-3,5-d₂ 
• 1514864-18-6 (2,6-d₂-4-methylphenyl)trimethylsilane 
• 54299-27-3 2,6-d₂-4-methylbromobenzene 
• 1620817-54-0 N-(p-tolyl)benzamide-d₂ 
• 740871-98-1 C₁₃H₁₇⁽²⁾H₂BO₂ 

Relevant academic research and scientific papers

Iridium-catalysed labelling of anilines, benzylamines and nitrogen heterocycles using deuterium gas and cycloocta-1,5-dienyliridium(I) 1,1,1,5,5,5-hexafluoropentane-2,4-dionate

A wide range of variously substituted anilines, benzylamines, and nitrogen heterocycles may be conveniently deuterated by exchange with deuterium gas and cycloocta-1,5-dienyliridium(I) 1,1,1,5,5,5-hexafluoropentane-2,4-dionate. The isotopic exchange can b

Mesoionic Carbene-Iridium Complex Catalyzed Ortho-Selective Hydrogen Isotope Exchange of Anilines with High Functional Group Tolerance

Mesoionic carbene-iridium complex 1a has been investigated in the hydrogen isotope exchange (HIE) reaction of anilines. By employing 1 mol % of 1a as catalyst, anilines were selectively deuterated at the ortho-position with high deuteration levels. High ortho-selectivity was observed for anilines with various competing directing groups, which is in contrast with catalytic results of Kerr's catalysts.

Ir-Catalyzed Intramolecular Transannulation/C(sp2)-H Amination of 1,2,3,4-Tetrazoles by Electrocyclization

An efficient strategy for the intramolecular denitrogenative transannulation/C(sp2)-H amination of 1,2,3,4-tetrazoles bearing C8-substituted arenes, heteroarenes, and alkenes is described. The process involves the generation of the metal-nitrene intermediate from tetrazole by the combination of [CpIrCl2]2 and AgSbF6. It has been shown that the reaction proceeds via an unprecedented electrocyclization process. The method has been successfully applied for the synthesis of a diverse array of α-carbolines and 7-azaindoles.

Copper(I)-Catalyzed regioselective amination of N -aryl imines using TMSN3 and TBHP: A route to substituted benzimidazoles

A novel and efficient copper-catalyzed amination of N-aryl imines is described. This one-pot, multicomponent reaction, in which imine acts as a directing group by chelating to the metal center, affords a potential route for the transformation of the commercial aryl amines, aldehydes, and azides into valuable benzimidazole structural units with wide substrate scope and diversity. The synthetic and mechanistic aspects are presented.

Gold-catalyzed oxidative coupling of arylsilanes and arenes: Origin of selectivity and improved precatalyst

The mechanism of gold-catalyzed coupling of arenes with aryltrimethylsilanes has been investigated, employing an improved precatalyst (thtAuBr3) to facilitate kinetic analysis. In combination with linear free-energy relationships, kinetic isotope effects, and stoichiometric experiments, the data support a mechanism involving an Au(I)/Au(III) redox cycle in which sequential electrophilic aromatic substitution of the arylsilane and the arene by Au(III) precedes product-forming reductive elimination and subsequent cycle-closing reoxidation of the metal. Despite the fundamental mechanistic similarities between the two auration events, high selectivity is observed for heterocoupling (C-Si then C-H auration) over homocoupling of either the arylsilane or the arene (C-Si then C-Si, or C-H then C-H auration); this chemoselectivity originates from differences in the product-determining elementary steps of each electrophilic substitution. The turnover-limiting step of the reaction involves associative substitution en route to an arene π-complex. The ramifications of this insight for implementation of the methodology are discussed.

Organocatalytic syntheses of benzoxazoles and benzothiazoles using aryl iodide and oxone via C-H functionalization and C-O/S bond formation

An organocatalytic protocol for the syntheses of 2-substituted benzoxazoles and benzothiazoles is described from alkyl-/arylanilides and alkyl-/arylthioanilides using 1-iodo-4-nitrobenzene as catalyst and oxone as an inexpensive and environmentally safe terminal oxidant at room temperature in air via oxidative C-H functionalization and C-O/S bond formation. The procedure is simple and general and provides an effective route for the construction of functionalized 2-alkyl-/arylbenzoxazoles and 2-alkyl-/arylbenzothiazoles with moderate to high yields. The synthetic and mechanistic aspects have been described.

Direct imidation to construct 1H-benzo[d]imidazole through Pd II-catalyzed C-H activation promoted by thiourea

A study was conducted to demonstrate the development of a method to construct 1H-benzo[d]immidazole through PdII -catalyzed intermolecular C-H activation starting from N-phenylbenziimidamide. The detailed mechanism investigations indicated that a palladacycle monomer or dimer was the key intermediate for this transformation, demonstrating that thiourea was first used to influence the efficiency of C-H activation. The method was found to construct 1H-benzo[d]immidazole through PdII -catalyzed intermolecular C-H activation extending the substrate scope widely. It also demonstrated the introduction of thiourea (tetramethylthiourea) (TMTU) for the first time as an additive to promote the efficiency of PdII catalysis for the direct C-H transformation. N-phenylbenziimidamide was also readily synthesized through the addition of aniline to benzonitrile according to the method to conduct the investigations.

Labelling of anilines, benzylamines and some N-heterocyclics using cycloocta-1,5-dienyliridium(I) -1,1,1,5,5,5-hexafluoro-pentan-2,4-dionate and isotopic hydrogen gas in DMF or DMA

A wide range of anilines, benzylamines and some N-heterocyclics can be ortho-deuterated at room temperature using deuterium gas and cycloocta-1,5-dienyliridium(I)-1,1,1,5,5,5-hexafluoropentan-2,4-dionate in DMF or DMA. The method is applicable to labellin