Mushroom tyrosinase catalysed coupling of hindered phenols : A novel approach for the synthesis of diphenoquinones and bisphenols

Pandey, Ganesh; Muralikrishna, C.; Bhalerao, U. T.

doi:10.1016/s0040-4039(00)97467-7

Cited by 33 publications

(14 citation statements)

References 7 publications

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“…This suggests that the copper complexes have an obvious comparative advantage in the oxidative coupling of DMP. In addition, central metal ion-exchanged products 2 and 3 perform identically with selectivity of almost 88%, which is comparable to that found for enzymes such as laccaese and tyrosinase [26]. The potential benefits of the heterogeneous catalyst include facilitation of catalyst separation from reagents and reaction products, and simplification of methods for catalyst recycling [27].…”

Section: Catalytic Oxidative Coupling Of Dmp In Watersupporting

confidence: 56%

Study on the reactions of zinc carboxylate complexes with copper(II) or cobalt(II) ions

Xiao

Chen

2014

Journal of Coordination Chemistry

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By immersion of selected big single crystals of [Zn(pc)(Phen)(H 2 O)] 2 ·6H 2 O (1; H 2 pc = 4-hydroxyphthalic acid) into aqueous solutions of Cu(NO 3 ) 2 and Co(NO 3 ) 2 , respectively, two central metal ion exchange induced SCTSC transformation products, [Cu 0.63 Zn 0.37 (pc)(Phen)(H 2 O)] 2 ·6H 2 O (2) and [Co 0.69 Zn 0.31 (pc)(Phen)(H 2 O)] 2 ·6H 2 O (3), can be obtained. As heterogeneous catalysts, central metal ion-exchanged products 2 and 3 showed high catalytic efficiency in the green oxidative polymerization of DMP. Our results indicate that central metal ion exchange might be regarded as a powerful and effective method to modify properties of crystalline materials only by varying central metal ions under moderate conditions. *Corresponding authors. Reaction of zinc carboxylate, [Zn(pc)(Phen)(H 2 O)] 2 ·6H 2 O (1; H 2 pc = 4-hydroxyphthalic acid), with Cu(NO 3 ) 2 or Co(NO 3 ) 2 is investigated. By immersion of single crystals of 1 into aqueous solutions of Cu(NO 3 ) 2 and Co(NO 3 ) 2 , respectively, metal ion exchange induced single-crystal to single-crystal (SCTSC) transformation products, [Cu 0.63 Zn 0.37 (pc)(Phen)(H 2 O)] 2 ·6H 2 O (2) and [Co 0.69 Zn 0.31 (pc) (Phen)(H 2 O)] 2 ·6H 2 O (3), could be obtained. As heterogeneous catalysts, central metal ionexchanged products 2 and 3 show high catalytic efficiency in the green oxidative polymerization of 2,6-dimethylphenol (DMP) to poly(1,4-phenylene ether) in the presence of H 2 O 2 as oxidant in water under mild conditions with reuse without significant loss of activity through three runs, which suggests that these catalysts are efficient, mild, and easily recyclable for the oxidative coupling of DMP.Our results indicate that central metal ion exchange might be a powerful and effective method to modify properties of crystalline materials by varying the central metal ions under moderate conditions.

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Section: Catalytic Oxidative Coupling Of Dmp In Watersupporting

confidence: 56%

Study on the reactions of zinc carboxylate complexes with copper(II) or cobalt(II) ions

Xiao

Chen

2014

Journal of Coordination Chemistry

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“…Concretely, the less steric hindrance around Cu II center in polymer 2 may ease more DMP molecules binding to Cu II centers to promote this oxidative coupling reaction, and the higher conversion is observed. In addition, both complexes perform identically the good selectivity of almost 90%, which is comparable to that found for enzymes such as laccese and tyrosinase [41,42]. As a result, further structure modification for Cu-containing MOFs could be obtained through objective molecular design and synthesis, and then enhance the catalytic properties for desired applications.…”

Section: Catalytic Properties Of Complexessupporting

confidence: 54%

Catalytic applications of CuII-containing MOFs based on N-heterocyclic ligand in the oxidative coupling of 2,6-dimethylphenol

Xiao

Hou

Fan

2007

Journal of Organometallic Chemistry

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“…G 4 -Cu 2+ 12 efficiently catalyzed the C–C selective coupling reaction of 2,6-substituted phenols including 2,6-diisopropylphenol ( 1b ) and 2- tert -butyl-6-methylphenol ( 1c ) to afford corresponding diphenoquinone derivatives ( 2b and 2c ) in 97% yields for 24 h ( Scheme 1 ). These results differ from those obtained with mushroom tyrosinase , where both 1b and 1c were not fully converted even after extending the reaction time [ 16 ]. The coupling reaction of unsubstituted phenol or phenol derivatives with electron-withdrawing chlorine atoms did not proceed, which is similar to the results obtained by other Cu catalyst systems [ 16 , 18 ].…”

Section: Resultscontrasting

confidence: 99%

“…Bhalerao et al reported the first demonstration of the regioselective coupling of DMP to DPQ by using enzyme mushroom tyrosinase in 1990. Mushroom tyrosinase , which has a dinuclear copper species as an active center, promotes the selective C–C coupling in a phosphate buffer solution at room temperature [ 16 ]. Since this report, several homogeneous catalysts have been developed [ 17 , 18 , 19 ].…”

Section: Introductionmentioning

confidence: 99%

Selective C–C Coupling Reaction of Dimethylphenol to Tetramethyldiphenoquinone Using Molecular Oxygen Catalyzed by Cu Complexes Immobilized in Nanospaces of Structurally-Ordered Materials

et al. 2015

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Two high-performance Cu catalysts were successfully developed by immobilization of Cu ions in the nanospaces of poly(propylene imine) (PPI) dendrimer and magadiite for the selective C–C coupling of 2,6-dimethylphenol (DMP) to 3,3',5,5'-tetramethyldiphenoquinone (DPQ) with O2 as a green oxidant. The PPI dendrimer encapsulated Cu ions in the internal nanovoids to form adjacent Cu species, which exhibited significantly high catalytic activity for the regioselective coupling reaction of DMP compared to previously reported enzyme and metal complex catalysts. The magadiite-immobilized Cu complex acted as a selective heterogeneous catalyst for the oxidative C–C coupling of DMP to DPQ. This heterogeneous catalyst was recoverable from the reaction mixture by simple filtration, reusable without loss of efficiency, and applicable to a continuous flow reactor system. Detailed characterization using ultraviolet-visible (UV-vis), Fourier transform infrared (FTIR), electronic spin resonance (ESR), and X-ray absorption fine structure (XAFS) spectroscopies and the reaction mechanism investigation revealed that the high catalytic performances of these Cu catalysts were ascribed to the adjacent Cu species generated within the nanospaces of the PPI dendrimer and magadiite.

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Mushroom tyrosinase catalysed coupling of hindered phenols : A novel approach for the synthesis of diphenoquinones and bisphenols

Cited by 33 publications

References 7 publications

Study on the reactions of zinc carboxylate complexes with copper(II) or cobalt(II) ions

Study on the reactions of zinc carboxylate complexes with copper(II) or cobalt(II) ions

Catalytic applications of CuII-containing MOFs based on N-heterocyclic ligand in the oxidative coupling of 2,6-dimethylphenol

Selective C–C Coupling Reaction of Dimethylphenol to Tetramethyldiphenoquinone Using Molecular Oxygen Catalyzed by Cu Complexes Immobilized in Nanospaces of Structurally-Ordered Materials

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