Schaugaard, Richard N.; Nguyen, Hien M.; Schlegel, H. Bernhard published the artcile< Alkyl Radical-Free Cu(I) Photo-catalytic Cross-Coupling: A Theoretical Study of Anomerically Specific Photo-catalyzed Glycosylation of Pyranosyl Bromide>, Recommanded Product: ((3aR,5R,5aS,8aS,8bR)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-5-yl)methanol, the main research area is reductive elimination transition state free energy cyclic voltammetry glycosylation; thermodn solvation chromophore copper iodide xantphos DTMP phenanthroline catalyst; photochem catalyzed glycosylation pyranosyl bromide cross coupling disaccharide preparation.
Previously, we reported a visible light-activated Cu(I) photocatalyst capable of facilitating C-O bond formation of glycosyl bromides and aliphatic alcs. with a high degree of diastereoselectivity. This catalyst functions equally well in the presence of radical traps, suggesting an entirely inner sphere mechanism atypical for heteroleptic Cu photocatalysis. Further, exptl. estimates put the chromophore reducing power at -1.30 V vs Ag/AgCl. This is much more pos. than the ~-2.0 V vs Ag/AgCl onset observed for irreversible reduction of glycosyl bromides in our experiments Theor. investigations were undertaken to explain the function of the catalyst. Outer sphere electron transfer from a chromophore to substrate was discounted based on thermodn. and electron transfer barriers determined by Marcus theory and non-equilibrium solvation calculations Addition of a nucleophilic alc. and oxidation of the Cu(II) species to Cu(III) result in rapid reductive elimination forming products and resetting the catalytic cycle.
Inorganic Chemistry published new progress about Catalysis. 4064-06-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C12H20O6, Recommanded Product: ((3aR,5R,5aS,8aS,8bR)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-5-yl)methanol.
Referemce:
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