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Regioselective 5‐endo‐dig Electrophilic Iodocyclization of Enediynes: A Convenient Route to Iodo‐substituted Indenes and Cyclopenta‐Fused Arenes
Author(s) -
Saunthwal Rakesh K.,
Danodia Abhinandan K.,
Patel Monika,
Kumar Sushil,
Verma Akhilesh K.
Publication year - 2016
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201601085
Subject(s) - regioselectivity , electrophile , chemistry , halogenation , combinatorial chemistry , medicinal chemistry , stereochemistry , organic chemistry , catalysis
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.