60006-28-2

Upstream product

• 123-75-1 pyrrolidine 
• 29882-02-8 N',N''-dicyclohexyl-N,N-dimethylguanidine 
• 538-75-0 dicyclohexyl-carbodiimide 

Downstream Products

• 1357859-68-7 BA/DCPG 
• 117688-53-6 C₄₂H₇₄N₈O₂ 

Relevant academic research and scientific papers

Ytterbium triflate: A highly active catalyst for addition of amines to carbodiimides to N,N′,N″-trisubstituted guanidines

(Chemical Equation Presented) Ytterbium triflate was found to be efficient catalyst for addition of amines to carbodiimides to N,N′,N″- trisubstituted guanidines with a wide scope of amines under solvent-free condition.

Synthesis and Reactivity of NNNNN-Pincer Multidentate Pyrrolyl Rare-Earth-Metal Amido-Chloride or Dialkyl Complexes

The NNNNN-pincer multidentate pyrrolyl rare-earth-metal amido-chloride complexes {η1:κ3-2,5-[CH3N(CH2CH2)2NCH2]2C4H2N}RECl[N(SiMe3)2] (RE = Y (2a), Sm (2b), Dy (2c), Er (2d), Yb (2e)) were synthesized by one step from reactions of [(Me3Si)2N]3RE(μ-Cl)Li(T

Cyclic (Alkyl)amino Carbene Complex of Aluminum(III) in Catalytic Guanylation Reaction of Carbodiimides

Herein we report the synthesis of a cyclic (alkyl)amino carbene (cAAC) complex of AlMe3. This complex was used as an efficient catalyst for the guanylation reaction of carbodiimides with primary arylamines and secondary amines to deliver guanidine derivatives in good to excellent yields. This catalytic protocol can tolerate a wide range of functional groups. Furthermore, the longevity of the catalyst was tested in successive catalytic cycles, which indicated a sustained catalytic activity over a multiple cycles. The mechanistic pathway was well understood with the help of stoichiometric reaction and DFT study.

Catalytic C-N bond formation in guanylation reaction by N-heterocyclic carbene supported magnesium(II) and zinc(II) amide complexes

The catalytic activity of N-heterocyclic carbene (NHC) supported magnesium(II) and a zinc(II) amide complex towards the addition of N-H bond of amine to carbodiimide was studied. Treatment of a free carbene i.e., 1,3-di-tert-butylimidazol-2-ylidene (ItBu) with magnesium and zinc bis(amide) i.e., M[N(SiMe3)2]2, M = Mg or Zn in toluene led to the formation of ItBu:M[N(SiMe3) 2]2, M = Mg(1) and Zn(2) compounds, respectively. Both 1 and 2 were characterized by multinuclear (1H, 13C and 29Si) NMR spectroscopy and single X-ray crystal structure analysis. Solid state structures revealed that both complexes are monomeric in nature and their magnesium and zinc atoms are three coordinated and distorted trigonal planar in geometries. Furthermore, compounds 1 and 2 were tested as catalysts for the guanylation reaction of addition of amine to carbodiimide and turned to be excellent catalysts.

Enol-functionalized N-heterocyclic carbene lanthanide amide complexes: Synthesis, molecular structures and catalytic activity for addition of amines to carbodiimides

Reaction of LnCl3 (Ln = Y, Nd, Sm and Yb) with enol-functionalized imidazolium salt H2LBr (L = 4-OMe-C 6H4COCH{C(NCHCHNiPr)}) and NaN(TMS)2 at a molar ratio of 1:4:1 in THF at room temperature afforded the corresponding novel enol-functionalized N-heterocyclic carbene (NHC) lanthanide amides L 2LnN(TMS)2 (Ln = Y (1), Nd (2), Sm (3), Yb (4)) in 37-40% yields. Molecular structures of 1-4 were determined by X-ray structure analyses. All complexes adopt monomeric structures where each 5-coordinated metal is coordinated by two NHC ligands and one amido group.in distorted trigonal bipyramid geometry. All complexes, especially Yb complex (4), were found to be highly active precatalysts for the catalytic addition of amines to carbodiimides giving guanidines. The system with 4 shows good functional group tolerance and a wide scope of amines including primary and secondary cyclic amines.

Catalytic guanylation of aliphatic, aromatic, heterocyclic primary and secondary amines using nanocrystalline zinc(II) oxide

Nanocrystalline ZnO was found to be a highly efficient heterogeneous catalyst for the guanylation of amines with various carbodiimides to afford N,N′,N″-trisubstituted guanidines in excellent yields. Structurally divergent aliphatic, aromatic, heterocyclic primary and secondary amines were converted to the corresponding N,N′,N″-trisubstituted guanidines using optimal conditions. The catalyst was easy to handle even under atmospheric conditions and can be easily recovered by centrifugation and reused for five cycles with consistent activity.

Heterobimetallic dianionic guanidinate complexes of lanthanide and lithium: Highly efficient precatalysts for catalytic addition of amines to carbodiimides to synthesize guanidines

A series of heterobimetallic dianionic guanidinate complexes of lanthanide and lithium, [Li(THF)(DME)]3Ln[μ- η2η1(iPrN)2C(NC 6H4p-R)]3 [R=Cl, Ln=Nd (I), Y (II), La (III); R=H, Ln=Nd (IV)] were synthesized and fully characterized. These complexes were found to be highly efficient precatalysts for the addition of various primary and secondary amines, and aromatic and aliphatic diamines to carbodiimides to give the corresponding monoguanidine and biguanidine derivatives under mild condition (at 25-60 °C), which provides an efficient way for the synthesis of biguanidines compounds. The activity depends on the central metals and ligands: La>Nd>Y for the metals and [(iPrN) 2C(NC6H4p-Cl)]2->[( iPrN)2C(NC6H5)]2- for the ligands were observed.

Catalytic Depolymerization of Polymers Containing Electrophilic Linkages Using Nucleophilic Reagents

The disclosure relates to methods and materials useful for depolymerizing a polymer. In one embodiment, for example, the disclosure provides a method for depolymerizing a polymer containing electrophilic linkages, wherein the method comprises contacting t

Acyclic guanidines as organic catalysts for living polymerization of lactide

We describe a facile route to structurally diverse guanidinium organic catalysts by reaction of carbodiimides with secondary amines. The efficacy of these catalysts for the living ring-opening polymerization (ROP) of lactide was demonstrated including predictable molecular weights and end-group fidelity. Theoretical studies indicate that the acyclic guanidines are less basic than 1, 5, 7-triazabicyclo[4.4.0]dec-5-ene (TBD), but as for the more active TBD, they catalyze ring opening by activation of the alcohol and by stabilizing the resultant tetrahedral intermediates through hydrogen bonding. These results demonstrate that weak secondary interactions are an important concept for controlled polymerization.

Titanacarborane mediated C-N bond forming/breaking reactions

Constrained-geometry titanacarboranes [σ:η1:η5-(OCH2)(R2NCH2)C2B9H9]Ti(NR2) (R = Me, Et) are synthesized via an unexpected reaction of [Me3NH][μ-7,8-CH2OCH2-7,8-C2B9H10] with Ti(NR2)4 (R = Me, Et), involving a C-O bond cleavage and C-N bond formation. These complexes can be readily converted to new amide species or alkoxide by reacting with amines or esters, respectively. Insertion of a series of unsaturated molecules into the Ti-N bond of the aforementioned complexes results in the formation of various half-sandwich titanacarboranes. [σ:η1:η5-(OCH2)(Me2NCH2)C2B9H9]Ti(NMe2) is also able to efficiently catalyze the hydroamination of carbodiimides and the transamination of guanidines. These results are summarized in this brief account.