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Upstream product

• 110-89-4 piperidine 
• 693-13-0 diisopropyl-carbodiimide 
• 68897-42-7 N′,N″-diisopropyl-N,N-dimethyl guanidine 
• 109-72-8 n-butyllithium 

Relevant academic research and scientific papers

Combination of air/moisture/ambient temperature compatible organolithium chemistry with sustainable solvents: Selective and efficient synthesis of guanidines and amidines

Highly-efficient and selective fast addition of in situ generated lithium amides [LiN(H)R] (obtained via an acid-base reaction between n-BuLi and the desired primary amine) into carbodiimides (R-NCN-R) or nitriles (R-CN) has been studied, for the first ti

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.

An amidato divalent ytterbium cluster: Synthesis and molecular structure, its reactivity to carbodiimides and application in the guanylation reaction

A divalent ytterbium amidate 1 ([Yb3L6]·2C7H8 for short) was synthesized via amine-elimination of Yb[N(SiMe3)2]2(TMEDA) with an amide proligand N-2,6-diisopropylphenylbenzamide HL (L = 2,6-iPr2C6H3NC(O)Ph) and structurally characterized to be a trinuclear symmetric cluster. Further studies on the reduction of iPrNCNiPr by complex 1 provide Yb(iii) complex 2 in hexane-THF ([(YbL2)2(μ-NiPrCNiPr)][YbL3(THF)]·C7H8), which is composed of two subunits in a unit cell, one is a bridged Yb(iii) carbene, just the same as complex 4 ([(YbL2)2(μ-NiPrCNiPr)]·3C7H8) obtained in the same reaction in toluene, and the other is a homoleptic monomeric Yb(iii) amidate (YbL3). It is also found that complex 2 decomposed to complex 3 ([YbL3]2·2C7H8) and 4 at 90 °C in toluene. Complexes 1-4 were confirmed by X-ray structure determination. Furthermore, complex 4 was proved to be a more active species than its precursor 1 in the catalytic addition of amines to carbodiimides. Finally, complex 1 was found to be an excellent pre-catalyst for the guanylation reaction with a wide scope of substrates.

Structural and Mechanistic Insights into s-Block Bimetallic Catalysis: Sodium Magnesiate-Catalyzed Guanylation of Amines

To advance the catalytic applications of s-block mixed-metal complexes, sodium magnesiate [NaMg(CH2SiMe3)3] (1) is reported as an efficient precatalyst for the guanylation of a variety of anilines and secondary amines with

Tris(pentafluorophenyl)borane as an efficient catalyst in the guanylation reaction of amines

Tris(pentafluorophenyl)borane, [B(C6F5)3], has been used as an efficient catalyst in the guanylation reaction of amines with carbodiimide under mild conditions. A combined approach involving NMR spectroscopy and DFT calcul

Phenylene-bridged β-Ketoiminate Dilanthanide Aryloxides: Synthesis, Structure, and Catalytic Activity for Addition of Amines to Carbodiimides

The synthesis and reactivity of a series of bimetallic lanthanide aryloxides stabilized by a p-phenylene-bridged bis(β-ketoiminate) ligand is presented. The reaction of 1,4-diaminobenzene with acetylacetone in a 1:2.5 molar ratio in absolute ethanol gave

Catalytic addition of amines to carbodIImides by bis(β-diketiminate)lanthanide(II) complexes and mechanistic studies

Reduction reactions of bis(β-diketiminate)lanthanide(iii) chlorides formed in situ by reactions of anhydrous LnCl3 with 2 equiv. of sodium salt of the β-diketiminate ligand in THF with a Na/K alloy afforded a series of bis(β-diketiminate)lanthanide(ii) complexes LnL2(THF)n (L = L26-Me2 = [N(2,6-Me2C6H3)C(Me)]2CH-, n = 1, Ln = Eu (1); L = L2,4,6-Me3 = [N(2,4,6-Me3C6H2)C(Me)]2CH-, n = 1, Ln = Eu (2); L = L2,6-iPr2 = [N(2,6-iPr2C6H3)C(Me)]2CH-, n = 0, Ln = Eu (3), Sm (4); L = L2,6-ipr2Ph = [(2,6-iPr2C6H3)NC(Me)CHC(Me)N(C6H5)]-, n = 0, Ln = Eu (5), Yb (6); L = L2-Me = [N(2-MeC6H4)C(Me)]2CH-, n = 1, Ln = Yb (7)) in high yields. All the complexes, especially the complexes of SmII (4) and EuII (5), were found to be excellent pre-catalysts for catalytic addition of amines to carbodiimides to multi-substituted guanidines with a wide scope of substrates. The activity depends both on the central metals and the ligands with the active sequence of YbII II and EuII II and L2,6-Me2 2,4,6-Me3 ～ L2,6-iPr2 2,6-ipr2Ph for the ligands. The mechanistic study by the isolation of guanidinate species and their reactivity revealed that EuII monoguanidinate complexes Eu(L2,6-Me2)[(C6H5N)C(NHCy)(NCy)](DME) (8) and Eu(L2,6-ipr2Ph)[(C6H5N)C(NHCy)(NCy)](THF)2 (9) should be the key active intermediates for the systems with EuII complexes and a YbIII bis(guanidinate) complex Yb(L2-Me)[(C6H5N)C(NHCy)(NCy)]2 (11) for the system using a YbII complex.

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.

Cyclopentadienyl-like ligand as a reactive site in half-sandwich bis(amidinato) rare-earth-metal complexes: An efficient application in catalytic addition of amines to carbodiimides

A series of mixed Cp′/bis(amidinato) (Cp′ = η5-C5Me4(SiMe3)) lanthanide complexes were synthesized by the 1:2 acid-base reaction between Cp′Ln(CH2SiMe3)2(THF) (Ln = Y, Dy, Er, Lu

Bridged bis(amidinate) lanthanide aryloxides: Syntheses, structures, and catalytic activity for addition of amines to carbodiimides

Various lanthanide aryloxide complexes supported by bridged bis(amidinate) ligand L, LLnOAr(DME) (L = Me3SiNC(Ph)N(CH2) 3NC(Ph)NSiMe3, DME = dimethoxyethane, Ln = Y, Ar = 2,6-(Me)2C6H3