Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Asymmetric Dipyrrin and F-BODIPYs Conjugated to Terminal Alkynes and Alkenes

Asymmetric Dipyrrin and F-BODIPYs Conjugated to Terminal Alkynes and Alkenes
Sarah Greening, Carlotta Figliola, Alison Thompson, Katherine N. Robertson
An asymmetric meso-H dipyrrin featuring a conjugated terminal alkyne substituent was converted to its corresponding difluoro boron complex, and the extent of π-conjugation was extended using Sonogashira cross-coupling. Treatment of the alkyne-substituted dipyrrin with BF3·OEt2 and NEt3 revealed the reactivity of the conjugated terminal alkyne toward Lewis-activated electrophilic substitution and led to the isolation of F-BODIPYs bearing terminal bromovinyl and enol substituents.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01129

DOI: 10.1021/acs.joc.7b01129

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