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Lam et al. have demonstrated via 18O-labeling studies that a phenol byproduct arises from water serving as an oxygen nucleophile, not via oxygen-atom transfer from O2: Lam, P. Y. S.; Bonne, D.; Vincent, G.; Clark, C. G.; Combs, A. P. Tetrahedron Lett. 2003, 44, 1691-1694.
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See Supporting Information for details.
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Three similar CuII species are evident under catalytic conditions; see Figure S2 for experimental and simulated EPR data. Very similar EPR spectra are obtained from solutions of Cu(OAc)2 and B(OMe)3 in methanol. In contrast, Cu(OAc)2 alone in methanol exists as a dimer that exhibits virtually no EPR signal (cf.: Rao, V. M.; Sathyanarayana, D. N.; Manohar, H. Ind. J. Chem. Sect. A1985, 24A, 417-418).
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Three similar CuII species are evident under catalytic conditions; see Figure S2 for experimental and simulated EPR data. Very similar EPR spectra are obtained from solutions of Cu(OAc)2 and B(OMe)3 in methanol. In contrast, Cu(OAc)2 alone in methanol exists as a dimer that exhibits virtually no EPR signal (cf.: Rao, V. M.; Sathyanarayana, D. N.; Manohar, H. Ind. J. Chem. Sect. A1985, 24A, 417-418).
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See, for example, refs 3c and 5.
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