Gold(I)-Catalyzed Reactions between -(-Alkynylphenyl)imines and Vinyldiazo Ketones to Form 3-(Furan-2-ylmethyl)-1-indoles via Postulated Azallyl Gold and Allylic Cation Intermediates.

This work describes gold-catalyzed additions of vinyldiazo ketones to -(-alkynylphenyl)imines to yield 3-(furan-2-ylmethyl)-1-indoles involving skeletal rearrangement; these new catalytic reactions are applicable to a wide range of substrates. We postulate a new mechanism involving an initial addition of diazo ketones to azomethine ylide intermediates to yield gold-containing -alkylated indole intermediates that undergo proton-induced 1,3-group migrations, generating azallyl gold and allylic cation pairs.