Gold(III)-Catalyzed Regioselective Oxidation/Cycloisomerization of Diynes: An Approach to Fused Furan Derivatives

Article abstract of DOI:10.1021/acs.orglett.8b01915

The first gold(III)-catalyzed regioselective oxidation/cycloisomerization of diynes 1 with pyridine N-oxide as the oxidant was developed, providing a range of synthetically valuable and useful fused furan derivatives 3 in moderate to good yields. Control experiments and the confirmation structure of minor products 5 suggest that this chemistry was a concerted gold(III)-catalyzed oxidation/S_N2′-type addition/cyclization process via a β-gold vinyloxypyridinium intermediate and a putative vinyl cation intermediate.