ZnII??and AuI??Catalyzed Regioselective Hydrative Oxidations of 3??En??1??ynes with Selectfluor: Realization of 1, 4??Dioxo and 1, 4??Oxohydroxy Functionalizations

AM Jadhav, SA Gawade, D Vasu…

Index: Jadhav, Appaso Mahadev; Gawade, Sagar Ashok; Vasu, Dhananjayan; Dateer, Ramesh B.; Liu, Rai-Shung Chemistry - A European Journal, 2014 , vol. 20, # 7 p. 1813 - 1817

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Citation Number: 11

Abstract

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 Zn II assists the hydrolysis ...