Gold-Catalyzed Divergent Ring-Opening Rearrangement of Cyclopropenes Enabled by Dichotomous Gold-Carbenes.

The gold-catalyzed ring-opening rearrangement of cyclopropenes affords an efficient route to either polysubstituted naphthols or aryl-substituted furans. Owing to the unique dichotomy of gold-carbenes, this protocol provides a switchable reaction selectivity between naphthols and furans enabled by the use of TFP-Au(MeCN)SbF 6 (tri(2-furyl) phosphine) or PNP(AuNTf 2 ) 2 (bis(diphenylphosphino)(isopropyl) amine) as catalysts respectively. It is proposed that the gold-carbene intermediate might be involved in the cyclopropene→naphthol rearrangement while the gold-carbocation is more likely to be involved in the cyclopropene→furan rearrangement.