2020
DOI: 10.1016/j.jorganchem.2020.121128
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Copper (II) immobilized on magnetically separable l-arginine-β-cyclodextrin ligand system as a robust and green catalyst for direct oxidation of primary alcohols and benzyl halides to acids in neat conditions

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Cited by 18 publications
(5 citation statements)
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“…The abstraction of a hydrogen radical from benzyl alcohol derivatives 2 produces benzyl radicals (I) which can react later with t-butylproxide radical to form the corresponding benzaldehyde (II) and regenerate Cu(II) species. [76][77][78] In the next step, aromatic aldehydes and malononitrile (3) are activated by the acidic sites of catalyst 1, respectively via a typical Knoevenagel condensation pathway. Eventually, the removal of one water molecule results in the desired products (4a-f).…”
Section: Resultsmentioning
confidence: 99%
“…The abstraction of a hydrogen radical from benzyl alcohol derivatives 2 produces benzyl radicals (I) which can react later with t-butylproxide radical to form the corresponding benzaldehyde (II) and regenerate Cu(II) species. [76][77][78] In the next step, aromatic aldehydes and malononitrile (3) are activated by the acidic sites of catalyst 1, respectively via a typical Knoevenagel condensation pathway. Eventually, the removal of one water molecule results in the desired products (4a-f).…”
Section: Resultsmentioning
confidence: 99%
“…Notably, substrates bearing ether substitutions were conducted at 120 °C to avoid hydrolysis. The deuteration of 3,5-dimethyl-and 3,5-difluorobenzoic acid (25,26) both showed excellent deuterium incorporation over 94%.…”
Section: Feature Synthesismentioning
confidence: 99%
“…Mp 102.1-102.4 °C (Lit. 25 104-108 °C); R f = 0.40 (petroleum ether/EtOAc, 6:1 + 1% CH 3 COOH). 1 H NMR (400 MHz, CDCl 3 ):  = 7.72 (dd, J = 7.6, 1.0 Hz, 0.07 H, labelled), 7.62 (d,J = 2.7 Hz,0.11 H,labelled),7.38 (d,J = 8.3 Hz,1 H),7.16 (d,J = 8.3 Hz,1 H),3.86 (s,3 H).…”
Section: Deuteration Of 3-methoxybenzoic Acid (17)mentioning
confidence: 99%
“…Heydari and coworkers have prepared support material 29-βCD-Fe 3 O 4 by reacting magnetic Fe 3 O 4 particles with L-arginin (100°C, 8 h) and then with tosylated βCD (toluene, reflux, 18 h) and, finally, treated the product with Cu(OAc) 2 (0.73 % Cu 2 + -29-βCD-Fe 3 O 4 ). [76] Characterization with instrumental methods (XRD, FT-IR, SEM, EDX, TGA, ICP) supported catalyst structure. Oxidation of primary alcohols with tert-butyl hydroperoxide (TBHP) gave the corresponding carboxylic acids in medium to high yields (Scheme 10).…”
Section: Oxidation Of Alcoholsmentioning
confidence: 99%