Litcius/Paper detail

Gold(I)-Catalyzed Cycloisomerization–Indole Addition Cascade: Synthesis of 3(2<i>H</i>)-Furanone-Incorporated Unsymmetrical 3,3′- Bis(indolyl)methanes

Debojyoti Bag, Sanghapal D. Sawant

2022Organic Letters18 citationsDOI

Abstract

An unprecedented Au(I)-catalyzed domino intramolecular carbonyl-alkyne cyclization/indole addition strategy has been disclosed here. This generalized strategy enables the synthesis of 3(2H)-furanone-incorporated unsymmetrical bis(indolyl)methanes with generation of a stereocenter at the furanone junction from easily accessible indole-tethered ynediones. In addition, this present protocol could also be extended for the synthesis of a number of indolyl-(hetero)arylmethanes by employing a variety of (hetero)arenes as a nucleophile coupling partner.

Topics & Concepts

Indole testChemistryCycloisomerizationStereocenterIntramolecular forceDominoCatalysisNucleophileCombinatorial chemistryAlkyneStereochemistryYield (engineering)Enantioselective synthesisOrganic chemistryMaterials scienceMetallurgyCatalytic Alkyne ReactionsSynthesis of Indole DerivativesCatalytic C–H Functionalization Methods