One-pot synthesis of tripodal tris(2-aminoethyl)amine derivatives from seven molecular components

Almesaker, Anne; Scott, Janet L.; Spiccia, Leone; Strauss, Christopher R.

doi:10.1016/j.tetlet.2009.02.008

Cited by 12 publications

(5 citation statements)

References 27 publications

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“…The solid state structure of (3) can be seen in Scheme 2. Like 2 has been seen in other aryl substituted tren ligands [18,19,21,25].…”

Section: Ligand Structuresmentioning

confidence: 54%

“…Though many different variations of the tren ligand have been prepared, the majority of the metalation work performed to date has been on tris(silyl)tren derivatives [2,[4][5][6][7][8][9][10][11]. The tris(aryl)tren ligand set has been explored to a lesser extent [12][13][14][15][16][17][18][19], but has shown great promise in the areas of nitrogen fixation [3] and in metal cluster formation [20].…”

Section: Introductionmentioning

confidence: 99%

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A modular synthesis of tris(aryl)tren ligands: Synthesis, structure and lithiation chemistry

Mdluli

Hubbard

Javier-Jimenez

et al. 2017

Inorganica Chimica Acta

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A modular synthesis of tris(aryl)tren ligands has been demonstrated via the condensation of nitrilotracetyl chloride with different anilines followed by reduction. Varying the aniline in the condensation step from 2-methylthioaniline, to 2-phenylthioaniline, to 2-chloroaniline, generates 2,2',2"-nitrilotris(N-(2-(methylthio)phenyl)acetamide (1), 2,2',2"-nitrilotris(N-(2-(phenylthio)phenyl)acetamide (2) and 2,2',2"-nitrilotris(N-2-chlorophenyl)acetamide (3) respectively. The 2-chloroaniline synthesis is complicated by the production of N-(2chlorophenyl)-3,5-dioxo-1-piperazine-N-(2-chlorophenyl)acetamide (4), but can be adjusted to produce only 3. The reduction of complexes 1-3 proceeds with lithium aluminum hydride for 1 and 2 and with borane for 3 to yield the tris(aryl)tren ligands tris-(2-(2-(methylthio)phenylamino)ethyl)amine (5), tris-(2-(2-(phenylthio)phenylamino)ethyl)amine (6), and tris-(2-(2-chlorophenylamino)ethyl)amine (7). All three of these ligands can be deprotonated with tert-butyllithium for 5 and 7, and n-butyllithium for 6 to generate their trilithium complexes, 8, 9 and 10 for 5, 6 and 7 respectively, with 10 forming two different solvates (10a and 10b). All complexes are characterized by 1 H and 13 C NMR and the solid state structures of complexes 2, 3, 4, 7, 8, 9, 10a and 10b are described.

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“…The solid state structure of (3) can be seen in Scheme 2. Like 2 has been seen in other aryl substituted tren ligands [18,19,21,25].…”

Section: Ligand Structuresmentioning

confidence: 54%

Section: Introductionmentioning

confidence: 99%

A modular synthesis of tris(aryl)tren ligands: Synthesis, structure and lithiation chemistry

Mdluli

Hubbard

Javier-Jimenez

et al. 2017

Inorganica Chimica Acta

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“…The solid state structure of (1) is shown in Figure 1 By contrast, the solid state structure of the reduced ligand (2) exhibits a folded arrangement, similar to that expected upon tripodal coordination of a metal center ( Figure 2). This arrangement has been observed for the structures of other aryl substituted tren ligands [24][25][26]. Polymorph 2a has crystallographically imposed three-fold symmetry, with one third of the ligand present in the asymmetric unit.…”

Section: Ligand Structuresmentioning

confidence: 54%

A tripodal aminothioether ligand scaffold: Synthesis and coordination to zirconium and hafnium

et al. 2017

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The heptadentate ligand, tris-(2-(2-(methylthio)phenylamino)ethyl)amine (2), has been synthesized from the condensation of nitrilotriacetyl chloride with 2-(methylthio)aniline, to generate 2,2',2"-nitrilotris(N-(2-(methylthio)phenyl)acetamide) (1), followed by a lithium aluminum hydride reduction. The zirconium (3) and hafnium (4) complexes of this ligand were generated via transamination reactions. Both complexes are isostructural, exhibiting a hexadentate N 4 S 2 coordination from the ligand, with one diethylamido ligand also bound. The solid state structures of all compounds are reported.

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“…The synthesis of the ligand (p-NO 2 BP) 3 tren has been reported elsewhere. [26] All manipulations were carried out in air. X-band EPR spectra were recorded with a Bruker EMX electron spin resonance spectrometer.…”

Section: Methodsmentioning

confidence: 99%

Distortional Isomerism in Copper(II) Nitrato Complexes of N,N′,N″‐Tris{[(para‐nitrobenzyl)phenyl]aminoethyl}amine

et al. 2010

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The tris(aminoethyl)amine derivative tris{ [(para-nitrobenzyl)phenyl]aminoethyl}amine [(p-NO 2 BP) 3 tren] was reacted with copper(II) nitrate in thf to yield three different solvates of [Cu(p-NO 2 BP) 3 trenNO 3 ]NO 3 (C1) in the solid state, namely α-C1·2thf (C2), β-C1·2.5thf (C3) and α-C1·(thf) 1.5 · (iPr 2 O) 0.25 (C4). The light green-yellow coloured complexes, C2 and C4, are different solvates of the one distortion isomer, while the dark-green C3 is a different distortion isomer. The spectral properties of these distortion isomers were examined, and the structures of C3 and C4 were determined by Xray crystallography. The difference in the physical properties (EPR and reflectance electronic spectra) of the light and dark

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One-pot synthesis of tripodal tris(2-aminoethyl)amine derivatives from seven molecular components

Cited by 12 publications

References 27 publications

A modular synthesis of tris(aryl)tren ligands: Synthesis, structure and lithiation chemistry

A modular synthesis of tris(aryl)tren ligands: Synthesis, structure and lithiation chemistry

A tripodal aminothioether ligand scaffold: Synthesis and coordination to zirconium and hafnium

Distortional Isomerism in Copper(II) Nitrato Complexes of N,N′,N″‐Tris{[(para‐nitrobenzyl)phenyl]aminoethyl}amine

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