An efficient copper-catalyzed solvent-switchable regioselective 1,2- or 1,6-addition of quinones with boronic acids has been developed. This novel catalytic protocol for the synthesis of various quinols and 4-phenoxyphenols was enabled by a simple solvent swap between H2O and MeOH. It features mild reaction conditions, simple and easy operation, broad substrate scope and excellent regioselectivity. The gram-scale reactions as well as the further transformations of both addition products were also successfully investigated.
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Univ Bologna, Dept Ind Chem Toso Montanari, Alma Mater Studiorum, V Risorgimento 4, I-40136 Bologna, Italy
Univ Bologna, INSTM RU Bologna, Alma Mater Studiorum, V Risorgimento 4, I-40136 Bologna, ItalyUniv Bologna, Dept Ind Chem Toso Montanari, Alma Mater Studiorum, V Risorgimento 4, I-40136 Bologna, Italy
Bertuzzi, Giulio
Lenti, Lucia
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Univ Bologna, Dept Ind Chem Toso Montanari, Alma Mater Studiorum, V Risorgimento 4, I-40136 Bologna, Italy
Univ Bologna, INSTM RU Bologna, Alma Mater Studiorum, V Risorgimento 4, I-40136 Bologna, Italy
Univ Camerino, Sch Sci & Technol, Chem Div, VS Agostino 1, I-62032 Camerino, ItalyUniv Bologna, Dept Ind Chem Toso Montanari, Alma Mater Studiorum, V Risorgimento 4, I-40136 Bologna, Italy
Lenti, Lucia
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Bisag, Denisa Giorgiana
Fochi, Mariafrancesca
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Univ Bologna, Dept Ind Chem Toso Montanari, Alma Mater Studiorum, V Risorgimento 4, I-40136 Bologna, Italy
Univ Bologna, INSTM RU Bologna, Alma Mater Studiorum, V Risorgimento 4, I-40136 Bologna, ItalyUniv Bologna, Dept Ind Chem Toso Montanari, Alma Mater Studiorum, V Risorgimento 4, I-40136 Bologna, Italy
Fochi, Mariafrancesca
Petrini, Marino
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Univ Camerino, Sch Sci & Technol, Chem Div, VS Agostino 1, I-62032 Camerino, ItalyUniv Bologna, Dept Ind Chem Toso Montanari, Alma Mater Studiorum, V Risorgimento 4, I-40136 Bologna, Italy