Unusual Intramolecular Hydrogen Transfer in 3,5-Di(triphenylethylenyl) BODIPY Synthesis and 1,2-Migratory Shift in Subsequent Scholl Type Reaction

Ming Hui Chua, Kuo-Wei Huang, Jianwei Xu, Jishan Wu

Research output: Contribution to journalArticlepeer-review

27 Scopus citations

Abstract

The straightforward synthesis of 3,5-di(triphenylethylenyl) BODIPYs 1–3 from the condensation of 2-(triphenylethylenyl) pyrrole with aryl aldehydes are surprisingly found to produce side products that are hydrogenated at one of the two triphenylethylene substituents. It was also observed that the subsequent Scholl type reaction of 1 resulted in a “1,2-migratory shift” of one triphenylethylene substituent in addition to a ring closing reaction. Preliminary investigations, including DFT calculations and isolation of intermediates, were conducted to study these unusual observations on BODIPY chemistry.
Original languageEnglish (US)
Pages (from-to)4168-4171
Number of pages4
JournalOrganic Letters
Volume17
Issue number17
DOIs
StatePublished - Aug 17 2015

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