title: Regioselective 5-endo-dig Electrophilic Iodocyclization of Enediynes: A Convenient Route to Iodo-substituted Indenes and Cyclopenta-Fused Arenes.
abstract: An efficient iodine-mediated regioselective tandem approach for the synthesis of symmetric and asymmetric iodo-substituted indenes and stereoselective cyclopenta [b]pyridine/thiophenes from easily accessible enediynes that proceeds by in situ formation of an iodonium intermediate followed by a regioselective 5-endo-dig cyclization has been described. The intramolecular electrophilic iodocyclization was selectively triggered by a distribution of electronic density along the alkyne bond. Subsequently, the iodo-substituted indenes were diversified by employing palladium-catalyzed cross-coupling reactions and the coupled products were further confirmed by X-ray crystallographic studies.
authors.affiliation: Department of Chemistry, University of Delhi, Delhi-, 110007, India.
authors.forename: Rakesh K
authors.initials: RK
authors.lastname: Saunthwal
authors.affiliation: Department of Chemistry, University of Delhi, Delhi-, 110007, India.
authors.forename: Abhinandan K
authors.initials: AK
authors.lastname: Danodia
authors.affiliation: Department of Chemistry, University of Delhi, Delhi-, 110007, India.
authors.forename: Monika
authors.initials: M
authors.lastname: Patel
authors.affiliation: Department of Chemistry, University of Delhi, Delhi-, 110007, India.
authors.forename: Sushil
authors.initials: S
authors.lastname: Kumar
authors.affiliation: Department of Chemistry, University of Delhi, Delhi-, 110007, India.
authors.forename: Akhilesh K
authors.initials: AK
authors.lastname: Verma
keywords: 5-endo-dig; electrophilic iodocyclization; enediynes; indenes; regioselective reactions