28139-64-2

Upstream product

• 14331-67-0 4-(4-methylphenyl)-3-phenyl-4H-1,2,4-triazole 
• 119072-55-8 tert-butylisonitrile 
• 501-60-0 1,2-di(p-tolyl)diazene 
• 106-49-0 p-toluidine 
• 104351-33-9 3,3-Dimethyl-N-p-tolyl-butyrimidoyl chloride 
• 36288-37-6 N-hydroxy-4-methylbenzenecarboximidoyl chloride 
• 726-42-1 di-p-tolylcarbodiimide 
• 80820-73-1 N¹-tert-Butyl-N¹-hydroxy-N²-phenylformamidin 
• 190712-80-2 TiCl₂(N-tert-butylimido)bischlorobis(pyridine)titanium(IV) 
• 622-58-2 p-Tolylisocyanate 
• 2101-86-2 p-methylazidobenzene 
• 917-95-3 t-butylnitrite 
• 72624-86-3 (3,3-Dimethyl-but-1-enylidene)-p-tolyl-amine 

Downstream Products

• 55305-60-7 N'-tert-butyl-N-4-methylphenyl urea 

Relevant academic research and scientific papers

Halogen-containing heteroaromatic carbenes of the 1,2,4-triazole series and their transformations

A series of new stable halogenated carbenes, 1-tert-butyl-3,4-diaryl-1,2,4-triazol-5-ylidenes, has been synthesized. According to quantum chemical calculations, 4-(2,3,4-trifluorophenyl)-substituted 1-tert-butyl-3,4-diaryl-1,2,4-triazol-5-ylidene is the l

Electrochemical Synthesis of Carbodiimides via Metal/Oxidant-Free Oxidative Cross-Coupling of Amines and Isocyanides

This work discloses an electrochemical oxidative cross-coupling of amines with aryl and aliphatic isocyanides. In an undivided cell, the reaction proceeds without involving any transition-metal catalyst, oxidant, or toxic reagents providing carbodiimides in good yields, thereby circumventing stoichiometric chemical oxidants, with H2 as the only byproduct. Moreover, carbodiimides were in situ converted into unsymmetrical ureas in moderate to good yields using an electricity ON-OFF strategy.

Carbodiimide Synthesis via Ti-Catalyzed Nitrene Transfer from Diazenes to Isocyanides

Simple Ti imido halide complexes such as [Br2Ti(NtBu)py2]2 are competent catalysts for the synthesis of unsymmetrical carbodiimides via Ti-catalyzed nitrene transfer from diazenes or azides to isocyanides. Both alkyl and aryl isocyanides are compatible with the reaction conditions, although product inhibition with sterically unencumbered substrates sometimes limits the yield when diazenes are employed as the oxidant. The reaction mechanism has been investigated both experimentally and computationally, wherein a key feature is that the product release is triggered by electron transfer from an η2-carbodiimide to a Ti-bound azobenzene. This ligand-to-ligand redox buffering obviates the need for high-energy formally TiII intermediates and provides further evidence that substrate and product "redox noninnocence" can promote unusual Ti redox catalytic transformations.

Sequential Pd(0)/Fe(III) Catalyzed Azide-Isocyanide Coupling/Cyclization Reaction: One-Pot Synthesis of Aminotetrazoles

A rapid and efficient synthesis of aminotetrazole from aryl azides, isocyanides, and TMSN3 is developed. The reaction is promoted by sequential Pd(0)/Fe(III) catalysis. The reaction sequence utilizes the Pd-catalyzed azide-isocyanide denitrogenative coupling reaction to generate unsymmetric carbodiimide in situ, which reacts with TMSN3 in the presence of FeCl3 in a single pot. The methodology has distinct advantages over traditional synthetic approaches where toxic Hg and Pb salts are employed at stoichiometric scale.

Palladium-catalyzed cross-coupling reaction of azides with isocyanides

An efficient palladium-catalyzed cross-coupling reaction of azides with isocyanides is developed, providing a general synthetic route to unsymmetric carbodiimides with excellent yields. This method shows a broad substrate scope, including not only aryl azides, but also unactivated benzyl and alkyl azides. Furthermore, from readily available substrates, Pd-catalyzed coupling with a tandem amine insertion cascade to obtain unsymmetric trisubstituted guanidines has been achieved in a one-pot fashion.

Synthesis of carbodiimides by I2/CHP-mediated cross-coupling reaction of isocyanides with amines under metal-free conditions

An I2/CHP-mediated cross-coupling reaction of isocyanides with readily accessible amines via C-N formation is described for carbodiimide synthesis in moderate to excellent yields. This represents a metal-free strategy for a coupling reaction of isocyanides with amines, and it provides an efficient approach for symmetric and unsymmetric functionalized carbodiimide derivative synthesis under mild conditions.

The efficient synthesis of carbodiimides using a titanium imido complex

An efficient rt synthesis of carbodiimides or ureas from the combination of a titanium imido complex 2 and a range of 12 aryl and aliphatic isocyanates is described. Control experiments suggest that carbodimide formation is via heterocumulene metathesis t

Cycloaddition of N-Aryl-tert-butylketenimines to Both Nitrosobenzene and 2-Methyl-2-nitrosopropane

Reactions of the ketenimines 1a, b with nitrosobenzene (2a) do not give the appropriate 1,2-oxazetidines such as 3Aa,b, but produce small amounts of the benzoxazoles 4a, b and the 1,4-benzoxazines 5Aa, b.However, from 1a-c and the nitrosoalkane 2b the analogous compounds 5Ba-c and/or 3Ba-c are formed (depending on conditions); mixtures of 1d-f and 2b afford 3Bd-f only.The heterocycles 4 and 5 are believed to arise through the intermediary cycloadduct 14/14'.

Reactions of N1-Hydroxyformamidines with Heterocumulenes

N1-Hydroxyformamidines and isocyanates react to yield N1-(carbamoyloxy)formamidines and/or 3-amino-1,2,4-oxazolidin-5-ones.Frequently the formation of ureas is observed.It can be explained by an oxidoreductive rearrangement to 1,3,5-trisubstituted biurets which undergo abstraction of isocyanate.Reactions with carbodiimides lead to 3-amino-5-imino-1,2,4-oxadiazolidines, ureas and carbodiimides not identical with the educts.