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Zn II ‐ and Au I ‐Catalyzed Regioselective Hydrative Oxidations of 3‐En‐1‐ynes with Selectfluor: Realization of 1,4‐Dioxo and 1,4‐Oxohydroxy Functionalizations
Author(s) -
Jadhav Appaso Mahadev,
Gawade Sagar Ashok,
Vasu Dhananjayan,
Dateer Ramesh B.,
Liu RaiShung
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201304322
Subject(s) - regioselectivity , selectfluor , chemoselectivity , chemistry , pyridine , catalysis , oxonium ion , medicinal chemistry , alkyne , hydrolysis , organic chemistry , combinatorial chemistry , ion
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 of key oxonium intermediate.