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Gold Catalysis: Oxepines from γ‐Alkynylfurans
Author(s) -
Hashmi A. Stephen K.,
Kurpejović Elzen,
Wölfle Michael,
Frey Wolfgang,
Bats Jan W.
Publication year - 2007
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200600653
Subject(s) - chemistry , furan , substituent , catalysis , phenol , phenols , chloride , tautomer , oxide , valence (chemistry) , medicinal chemistry , organic chemistry , photochemistry
A ketal group in a furyl position affords arene oxides from γ‐alkynylfurans even with the simple gold(III) chloride (AuCl 3 ) catalyst. These can either undergo Diels–Alder reactions, isomerise to stable oxepines by an oxygen‐walk reaction or by the addition of water selectively be converted to phenols which differ in the position of the hydroxy group from the normal phenols formed in the gold‐catalysed phenol synthesis. With a phenyl substituent on the furan, the 2‐hydroxymethylpyridinato‐gold(III) complex, not the usual arene oxide but an oxepine is obtained, still the arene oxide can be trapped from the valence‐tautomeric equilibrium by a Diels–Alder reaction.