Unusual Intramolecular Hydrogen Transfer in 3,5-Di(triphenylethylenyl) BODIPY Synthesis and 1,2-Migratory Shift in Subsequent Scholl Type Reaction.
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.
Institute of Materials Research and Engineering, A*STAR , 3 Research Link, Singapore, 117602, Singapore.|Department of Chemistry, National University of Singapore , 3 Science Drive 3, Singapore, 117543, Singapore.
Ming Hui
MH
Chua
Division of Physical and Life Sciences and Engineering and KAUST Catalysis Center, King Abdullah University of Science and Technology (KAUST) , Thuwal 23955-6900, Saudi Arabia.
Kuo-Wei
KW
Huang
Institute of Materials Research and Engineering, A*STAR , 3 Research Link, Singapore, 117602, Singapore.
Jianwei
J
Xu
Institute of Materials Research and Engineering, A*STAR , 3 Research Link, Singapore, 117602, Singapore.|Department of Chemistry, National University of Singapore , 3 Science Drive 3, Singapore, 117543, Singapore.
Jishan
J
Wu