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New copper(II) salicylaldimine derivatives for mild oxidation of cyclohexane

Busa, Asanda V. ; Lalancette, Roger ; Nordlander, Ebbe LU and Onani, Martin (2018) In Journal of Chemical Sciences 130(6).
Abstract

Abstract: Two new salicylaldiminato-copper(II) complexes, [Cu(L1)2] (1) and [Cu(L2)2] (2) (where HL1= 4 -tert-Butyl-2-[(thiophen-2-ylmethylimino)-methyl]-phenol and HL2= 2 , 4 -Di-tert-butyl-6-[(thiophen-2-ylmethylimino)-methyl]-phenol), endowed with a pendant thiophenyl moiety, were synthesized and characterized using standard spectroscopic techniques (FT-IR, UV-Vis, MS) and elemental analysis. Complexes 1 and 2 were unequivocally characterized by single crystal X-ray crystallography, which confirmed bidentate bis-chelation of the deprotonated -L1 and -L2 ligands to the copper (II) centres via the phenoxo and imine atoms forming square planar complexes. The copper(II)-hydroperoxo derivatives... (More)

Abstract: Two new salicylaldiminato-copper(II) complexes, [Cu(L1)2] (1) and [Cu(L2)2] (2) (where HL1= 4 -tert-Butyl-2-[(thiophen-2-ylmethylimino)-methyl]-phenol and HL2= 2 , 4 -Di-tert-butyl-6-[(thiophen-2-ylmethylimino)-methyl]-phenol), endowed with a pendant thiophenyl moiety, were synthesized and characterized using standard spectroscopic techniques (FT-IR, UV-Vis, MS) and elemental analysis. Complexes 1 and 2 were unequivocally characterized by single crystal X-ray crystallography, which confirmed bidentate bis-chelation of the deprotonated -L1 and -L2 ligands to the copper (II) centres via the phenoxo and imine atoms forming square planar complexes. The copper(II)-hydroperoxo derivatives of 1 and 2 ([(L1)2CuII-OOH] (3) and [(L2)2CuII-OOH] (4)) were also synthesized and the formation of the active intermediate in solution studied. Complexes 1 and 2 were tested as catalyst precursors in cyclohexane oxidation under mild reaction conditions using hydrogen peroxide (H 2O 2) as a terminal oxidant, and were found to catalyse oxidation of the substrate with yields comparable to similar mononuclear and even multinuclear copper complexes. Graphical Abstract: Synopsis Synthesis, characterisation, and molecular structure of salicylaldiminato-copper(II) complexes, and their catalytic evaluation in the oxidation of cyclohexane employing hydrogen peroxide as a terminal oxidant have been studied. The complexes catalysed conversion of cyclohexane with appreciable yields. [Figure not available: see fulltext.].

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author
; ; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
Copper, cyclohexane, hydroperoxo complex, oxidation
in
Journal of Chemical Sciences
volume
130
issue
6
article number
59
publisher
Indian Academy of Sciences
external identifiers
  • scopus:85047461224
ISSN
0974-3626
DOI
10.1007/s12039-018-1455-y
language
English
LU publication?
yes
id
6002c70f-757c-43e1-9fbd-8fcdd8bf6b94
date added to LUP
2018-06-05 10:34:57
date last changed
2022-03-25 02:15:12
@article{6002c70f-757c-43e1-9fbd-8fcdd8bf6b94,
  abstract     = {{<p>Abstract: Two new salicylaldiminato-copper(II) complexes, [Cu(L1)2] (1) and [Cu(L2)2] (2) (where HL<sup>1</sup>= 4 -tert-Butyl-2-[(thiophen-2-ylmethylimino)-methyl]-phenol and HL<sup>2</sup>= 2 , 4 -Di-tert-butyl-6-[(thiophen-2-ylmethylimino)-methyl]-phenol), endowed with a pendant thiophenyl moiety, were synthesized and characterized using standard spectroscopic techniques (FT-IR, UV-Vis, MS) and elemental analysis. Complexes 1 and 2 were unequivocally characterized by single crystal X-ray crystallography, which confirmed bidentate bis-chelation of the deprotonated -L<sup>1</sup> and -L<sup>2</sup> ligands to the copper (II) centres via the phenoxo and imine atoms forming square planar complexes. The copper(II)-hydroperoxo derivatives of 1 and 2 ([(L1)2CuII-OOH] (3) and [(L2)2CuII-OOH] (4)) were also synthesized and the formation of the active intermediate in solution studied. Complexes 1 and 2 were tested as catalyst precursors in cyclohexane oxidation under mild reaction conditions using hydrogen peroxide (H <sub>2</sub>O <sub>2</sub>) as a terminal oxidant, and were found to catalyse oxidation of the substrate with yields comparable to similar mononuclear and even multinuclear copper complexes. Graphical Abstract: Synopsis Synthesis, characterisation, and molecular structure of salicylaldiminato-copper(II) complexes, and their catalytic evaluation in the oxidation of cyclohexane employing hydrogen peroxide as a terminal oxidant have been studied. The complexes catalysed conversion of cyclohexane with appreciable yields. [Figure not available: see fulltext.].</p>}},
  author       = {{Busa, Asanda V. and Lalancette, Roger and Nordlander, Ebbe and Onani, Martin}},
  issn         = {{0974-3626}},
  keywords     = {{Copper; cyclohexane; hydroperoxo complex; oxidation}},
  language     = {{eng}},
  month        = {{06}},
  number       = {{6}},
  publisher    = {{Indian Academy of Sciences}},
  series       = {{Journal of Chemical Sciences}},
  title        = {{New copper(II) salicylaldimine derivatives for mild oxidation of cyclohexane}},
  url          = {{http://dx.doi.org/10.1007/s12039-018-1455-y}},
  doi          = {{10.1007/s12039-018-1455-y}},
  volume       = {{130}},
  year         = {{2018}},
}