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

Carlotta Figliola (1) , Katherine N Robertson (2) , Sarah Greening (1) , Alison Thompson (1)

1 Dalhousie University [Halifax]
2 Saint Mary's University [Halifax]

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 BF 3 ·OEt 2 and NEt 3 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.

Domaines: Chimie organique

Carlotta Figliola, Katherine N Robertson, Sarah Greening, Alison Thompson. Asymmetric Dipyrrin and F-BODIPYs Conjugated to Terminal Alkynes and Alkenes. Journal of Organic Chemistry, 2017, 82 (13), pp.7059-7064. ⟨10.1021/acs.joc.7b01129⟩. ⟨hal-01588477⟩