227805-06-3

Upstream product

• 102-54-5 ferrocene 
• 1483-42-7 N,N'-dibenzyl-N,N'-dimethylmethylenediamine 
• 50-00-0 formaldehyd 
• 12093-10-6 ferrocenecarboxaldehyde 
• 103-67-3 benzyl-methyl-amine 

Downstream Products

• 913171-03-6 rac-σPt[(η5-Cp)Fe(η5-C5H3-CH2N(methyl)-benzyl)](chloride)(DMSO) 
• 1192236-43-3 1-formyl-2-[[methyl(phenylmethyl)amino]methyl]ferrocene 
• 515836-39-2 C₅H₅FeC₅H₃CH₃CH₂N(CH₃)2CH₂C₆H₅⁽¹⁺⁾*I^(1-)=[C₅H₅FeC₅H₃CH₃CH₂N(CH₃)2CH₂C₆H₅]I 

Relevant academic research and scientific papers

Dealkylation reactions of dialkylaminomethylferrocenes with cyclic chlorocarbaphosphazene, (ClCN)2(Cl2PN)

Dialkylaminomethylferrocenes, FcCH2NRR′ (NRR′=NMe2 (1), NEt2 (2), N(CH2CH=CH2)2 (3), N(CH2CH2)2O (4), N(Me)(CH2Ph) (5) and N(Me)(c-C6H11) (6) (Fc=Ferrocenyl) were synthesized by the reaction of ferrocene with the corresponding diamines, RR′NCH2NRR′. The identity of 3 was further confirmed by X-ray structural analysis of its hydrochloride, FcCH2NH(CH2CH=CH2)2 +Cl- (7). Reactions of compounds 1-6 were carried out with tetrachlorodicarbaphosphatriazene, (ClCN)2(Cl2PN) in diethylether medium at room temperature or in refluxing toluene. The amines 1, 2, 4, 5 and 6 were found to undergo a facile C-N bond cleavage at the bridging methylene group irrespective of the nature of substituents on the nitrogen. The cleaved dialkylamino groups were found to substitute regiospecifically at the ring carbon atoms of the carbaphosphazene, yielding the dialkylamino substituted carbaphosphazenes [(RR′N)CN]2(Cl2PN) 8-12. The X-ray crystal structure of the substituted carbaphosphazene (Me2NCN)2(Cl2PN) 8 has also been determined.

Room-Temperature Chemoselective Reductive Alkylation of Amines Catalyzed by a Well-Defined Iron(II) Complex Using Hydrogen

A transition-metal frustrated Lewis pair approach has been envisaged to enhance the catalytic activity of tricarbonyl phosphine-free iron complexes in reduction of amines. A new cyclopentadienyl iron(II) tricarbonyl complex has been isolated, fully characterized, and applied in hydrogenation. This phosphine-free iron complex is the first Earth-abundant metal complex that is able to catalyze chemoselective reductive alkylation of various functionalized amines with functionalized aldehydes. Such selectivity and functionality tolerance (alkenes, esters, ketones, acetals, unprotected hydroxyl groups, and phosphines) have been demonstrated also for the first time at room temperature with an Earth-abundant metal complex. This alkylation reaction was also performed without any preliminary condensation and generated only water as a byproduct. The resulting amines provided rapid access to potential building blocks, metal ligands, or drugs. Density functional theory calculations highlighted first that the formation of the 16 electron species, via the activation of the tricarbonyl complex Fe3, was facilitated and, second, that the hydrogen cleavage did not follow the same pathway as bond breaking, usually described with the known cyclopentadienone iron tricarbonyl complexes (Fe1 and Fe4). These calculations highlighted that the new complex Fe3 does not behave as a bifunctional catalyst, in contrast to its former congeners.

Synthesis, characterization, and anti-amoebic screening of core-modified 5,20-bis{2-{[(alkyl)(alkyl′)amino]methyl}ferrocen-1-yl}-10,15-diphenyl-21, 23-dithiaporphyrin (=1,1″-(10,15-diphenyl-21,23-dithiaporphine-5,20-diyl) bis[2-{[(alkyl)(alkyl′)amino]methyl}ferrocene]) derivatives

The synthesis of the first bis-ferrocenyl-substituted core-modified porphyrins, 5,20-bis{2-{[(alkyl)-(alkyl′)amino]methyl}ferrocen-1-yl}-10, 15-diphenyl-21,23-dithiaporphyrin derivatives 6a - 6j, via a multistep route is reported (Schemes 1, 2, and 4). The synthesis was carried out through acid-catalyzed (BF3 ? Et2O) condensation of 1,1″- [thiophene-2,5-diylbis(hydroxymethyl)]bis[2-{[(alkyl)(alkyl′)amino]methyl} ferrocenes] 4a - 4j with 2,2′-[thiophene-2,5-diylbis(phenylmethylene)] bis[1H-pyrrole] (5b) in presence of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (=4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile; DDQ). Characterization of the compounds was done at each step by means of various spectroscopic techniques. The final compounds were screened for in vitro anti-amoebic activity against the strain HM1:IMSS of E. histolytica (Table 2).

Synthesis, characterization of [{(N-methyl-N-benzyl)amino}methyl]ferrocenes and their cyclopalladated complexes: Crystal structure of σ-Pd[(η5-C5H5)Fe(η5-C5H3CH2N(CH3)

Condensation of aminomethylferrocene (1) and substituted benzaldehydes resulted in aldimines 2a-c which followed by reduction with sodium borohydride to give 3a-c. N-methylation of 3a-c with HCHO/NaCNBH3/HOAc led to 4a-c. Treatment of 4a-c with

Lithiation of ferrocenylamines and vanadium dinitrogen chemistry

The lithiation of ferrocenylamines [Fe(C5H5) (C5H4CH2R)] (R = NMe2, NEt2, CH2NMe2, NC4H8O or NMeCH2Ph) with organolithium reagents does not proceed with clean reaction at position 2 of the ring. Generally a range of products is formed, these sometimes difficult to separate. The electronic condition of the iron in these complexes as tested by M?ssbauer spectroscopy and electrochemistry, does not differ much between compounds. The crystal structures of several methylated derivatives of the ferrocenylamines are reported. All the ferrocenylamines seem to potentiate vanadium(II) to dinitrogen uptake, but the precise nature of the dinitrogen species formed could not be determined.