Proposal for halogen atom transfer mechanism for Ullmann O-arylation of phenols with aryl halides.

  title={Proposal for halogen atom transfer mechanism for Ullmann O-arylation of phenols with aryl halides.},
  author={Songlin Zhang and Zhenzhong Zhu and Yuqiang Ding},
  journal={Dalton transactions},
  volume={41 45},
A systematic theoretical study on reaction mechanisms for copper(I)-catalyzed C-O coupling of phenols with aryl bromides is reported herein. Through evaluation of the relative concentrations of possible copper species in reaction solution and reactivity study of these copper species with aryl halides in the context of several commonly proposed mechanisms for copper(I)-catalyzed Ullmann reactions, we propose that the active copper catalyst should be a neutral (L)Cu(I)-OAr (L denotes an ancillary… CONTINUE READING
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Br) -3749.566709 0.260656 0.281851 0.207315 -2.27 (phen)Cu(I)(O-Ph-p-CF3) -1413

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Cu(II)(O-Ph-p-CF3)(Br) -3987

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Electronic Energies, Zero-Point Vibrational Energies, Thermal Corrections to Enthalpies and Gibbs Free Energies and Solvation Energies in Toluene

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Electronic Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2012 Halogen atom transfer mechanism Ph @BULLET -231

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Note: SP: Single point electronic energy; ZPE: Zero-point vibrational energy; ∆H: Thermal correction to enthalpy; ∆G: Thermal correction to Gibbs free energy; Gsol : Solvation energy in toluene

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O-Ph-p-Me)(Br) -3689.624445 0.296347 0.318607 0.24118 -2.12 (phen)Cu(I)(O-Ph-p-OMe) -1190

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Substituent effect for (phen)Cu(OAr) (phen)Cu(I)(O-Ph-p-Me) -1115

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