Swiss Science Concentrates

Y. Li, J. P. Brand, and J.Waser*, Angew. Chem. Int. Ed. 2013, 52, 6743. EPF Lausanne Furan rings are a common structural motif found in many functional organic materials, bioactive compounds and natural products. In this communication, Waser and co-workers outline a selective and efficient access to C(2)or C(3)-alkynylated furans using gold catalysis. Direct C–H alkynylation at C(2) was achieved using hypervalent TIPS-ethynylbenziodoxolone in combination with aAu catalyst. For the C(3)-selective variation, a modification of the ethynyl reagent was required. Replacement of the carbonylby two trifluoromethyl groups enabled a domino cyclization/alkynylation process, relying on allenes as starting material in combination with a Au precursor. The broad substrate scope, good yields and mild conditions open fascinating perspectives for this novel methodology.