ZnII‐ and AuI‐Catalyzed Regioselective Hydrative Oxidations of 3‐En‐1‐ynes with Selectfluor: Realization of 1,4‐Dioxo and 1,4‐Oxohydroxy Functionalizations |
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| Authors: | Dr. Appaso Mahadev Jadhav Sagar Ashok Gawade Dr. Dhananjayan Vasu Dr. Ramesh B. Dateer Prof. Dr. Rai‐Shung Liu |
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| Affiliation: | Department of Chemistry, National Tsing Hua University, Hsinchu, 30013 (Taiwan), Fax: (+886)?3‐5711082 |
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| Abstract: | Catalytic 1,4‐dioxo functionalizations of 3‐en‐1‐ynes to (Z)‐ and (E)‐2‐en‐1,4‐dicarbonyl compounds are described. This regioselective difunctionalization was achieved in one‐pot operation through initial alkyne hydration followed by in situ Selectfluor oxidation. The presence of pyridine alters the reaction chemoselectivity to give 4‐hydroxy‐2‐en‐1‐carbonyl products instead. A cooperative action of pyridine and ZnII assists the hydrolysis of key oxonium intermediate. |
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| Keywords: | 1,4‐enediones 1,4‐oxohydroxy 3‐en‐1‐ynes hydrative oxidations regioselective difunctionalizations |
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