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

Citation data:

Organic letters, ISSN: 1523-7052, Vol: 17, Issue: 17, Page: 4168-71

Publication Year:
2015
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Abstract Views 10
Captures 21
Readers 21
Citations 15
Citation Indexes 15
Repository URL:
http://hdl.handle.net/10754/575663
PMID:
26280104
DOI:
10.1021/acs.orglett.5b01916
Author(s):
Chua, Ming Hui; Huang, Kuo-Wei; Xu, Jianwei; Wu, Jishan
Publisher(s):
American Chemical Society (ACS); American Chemical Society
Tags:
Chemistry; Biochemistry, Genetics and Molecular Biology
article description
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.