Gold(I)-Catalyzed Reactions between <i>N</i>-(<i>o</i>-Alkynylphenyl)imines and Vinyldiazo Ketones to Form 3-(Furan-2-ylmethyl)-1<i>H</i>-indoles via Postulated Azallyl Gold and Allylic Cation Intermediates
Antony Sekar Kulandai Raj, Akshay Subhash Narode, Rai‐Shung Liu
Abstract
This work describes gold-catalyzed additions of vinyldiazo ketones to N-(o-alkynylphenyl)imines to yield 3-(furan-2-ylmethyl)-1H-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 N-alkylated indole intermediates that undergo proton-induced 1,3-group migrations, generating azallyl gold and allylic cation pairs.
Topics & Concepts
ChemistryYield (engineering)FuranCatalysisDiazoIndole testMedicinal chemistryYlideAllylic rearrangementAlkylationOrganic chemistryMetallurgyMaterials scienceCatalytic Alkyne ReactionsCyclopropane Reaction MechanismsCatalytic C–H Functionalization Methods