13471-32-4

Upstream product

• 67-56-1 methanol 
• 726-42-1 di-p-tolylcarbodiimide 
• 124-41-4 sodium methylate 
• 13471-23-3 ClB{N(C₂H₅)2}{N(C₆H₄CH₃)((C(NC₆H₄CH₃)N(C₂H₅)2))} 
• 13471-15-3 ClB{N(C₆H₄CH₃)(C((NC₆H₄CH₃))C₆H₅)}{N(C₆H₄CH₃)(C((NC₆H₄CH₃))Cl)} 
• 13471-13-1 ClB{N(C₆H₄CH₃)(C((NC₆H₄CH₃))Cl)}2 
• 13471-14-2 BrB{NC₆H₄CH₃(C(NC₆H₄CH₃)Br)}2 
• 14335-26-3 CH₃O-BC₆H₅-NC₆H₄CH₃-C(=NC₆H₄-CH₃)OCH₃ 

Downstream Products

• 26292-51-3 dibenzyl methyl phosphate 

Relevant academic research and scientific papers

Catalytic Addition of Alcohols to Carbodiimides Mediated by Benzimidazolin-2-iminato Actinide Complexes

The synthesis of methyl and methoxy substituted benzimidazolin-2-iminato actinide (IV) complexes (1-4), [(Bim2-MeOPh/MeN)AnN″3] and [(Bim5-MeDipp/MeN)AnN″3] (An = U, Th; N″ = N(SiMe3)2

Benzimidazolin-2-iminato Hafnium Complexes: Synthesis, Characterization, and Catalytic Addition of Alcohols to Carbodiimides

A series of asymmetric imidazolin-2-iminato and benzimidazolin-2-iminato hafnium(IV) complexes were synthesized and fully characterized including single-crystal X-ray diffraction. The asymmetric imidazolin-2-iminato hafnium complex exhibits a shorter Hf-N

Metal-Free and Alkali-Metal-Catalyzed Synthesis of Isoureas from Alcohols and Carbodiimides

The first addition of alcohols to carbodiimides catalyzed by transition-metal-free compounds employs 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) and its alkali metal salts. Isoureas are obtained in short reaction times and high yields when TBDK is used as the catalyst. Control of the coordination sphere of potassium with exogenous chelating ligands, in combination with mechanistic DFT calculations, demonstrated the role and positive influence of the alkali-metal cation on the kinetics.

Actinide-Catalyzed Intermolecular Addition of Alcohols to Carbodiimides

The unprecedented actinide-catalyzed addition of alcohols to carbodiimides is presented. This represents a rare example of thorium-catalyzed transformations of an alcoholic substrate and the first example of uranium complexes showing catalytic reactivity with alcohols. Using the uranium and thorium amides U[N(SiMe3)2]3 and [(Me3Si)2N]2An[κ2-(N,C)-CH2Si(CH3)2N(SiMe3)] (An = Th or U), alcohol additions to unsaturated carbon-nitrogen bonds are achieved in short reaction times with excellent selectivities and high to excellent yields. Computational studies, supported by experimental thermodynamic data, suggest plausible models of the profile of the reaction which allow the system to overcome the high barrier of scission of the actinide-oxygen bond. Accompanied by experimentally determined kinetic parameters, a plausible mechanism is proposed for the catalytic cycle.

Actinide complexes possessing six-membered N-heterocyclic iminato moieties: Synthesis and reactivity

A novel class of ligand systems possessing a sixmembered N-heterocyclic iminato [perimidin-2-iminato (PrRN, where R = isopropyl, cycloheptyl)] moiety is introduced. The complexation of these ligands with early actinides (An = Th and U) results in powerful catalysts [(PrRN)An(N{SiMe3)2}3] (3-6) for exigent insertion of alcohols into carbodiimides to produce the corresponding isoureas in short reaction times with excellent yields. Experimental, thermodynamic, and kinetic data as well as the results of stoichiometric reactions provide cumulative evidence that supports a plausible mechanism for the reaction.

Catalytic Addition of Alcohols into Carbodiimides Promoted by Organoactinide Complexes

The insertion of alcohols into carbodiimides mediated by benzimidazolin-2-iminato actinide complexes [(BimR1/R2N)AnN3] [N = N(SiMe3)2] is presented herein. Analysis of single-crystal data revealed that steric hindrance, rather than electronic properties, plays an important role in determining the accessibility for this insertion process. All actinide complexes showed excellent activities under very mild conditions. Stoichiometric reactions in combination with kinetic and thermodynamic studies allow us to propose a plausible active species and a mechanism for the catalytic cycle.