18907-07-8Relevant academic research and scientific papers
Regioselective 5-endo-dig Electrophilic Iodocyclization of Enediynes: A Convenient Route to Iodo-substituted Indenes and Cyclopenta-Fused Arenes
Saunthwal, Rakesh K.,Danodia, Abhinandan K.,Patel, Monika,Kumar, Sushil,Verma, Akhilesh K.
supporting information, p. 3001 - 3007 (2016/11/13)
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.
Synthesis and structure of conjugated molecules with the benzofulvene core
Martinelli, Carmela,Cardone, Antonio,Pinto, Vita,Mastropasqua Talamo, Maurizio,D'Arienzo, Maria Luisa,Mesto, Ernesto,Schingaro, Emanuela,Scordari, Fernando,Naso, Francesco,Musio, Roberta,Farinola, Gianluca M.
supporting information, p. 3424 - 3427 (2014/07/21)
A general method to synthesize conjugated molecules with a benzofulvene core is reported. Up to four conjugated substituents have been introduced via a three-step sequence including (1) synthesis of 1,2-bis(arylethynyl)benzenes; (2) exo-dig electrophilic cyclization promoted by iodine; and (3) cross-coupling reaction of the resulting bis-iodobenzofulvenes with organoboron, organotin, or ethynyl derivatives under Pd catalysis. Structural aspects of the new compounds are discussed.
