Synthesis of 3,8-dichloro-6-ethyl-1,2,5,7-tetramethyl-BODIPY from an asymmetric dipyrroketone and reactivity studies at the 3,5,8-positions

Chemistry : a European Journal
Ning ZhaoKevin M Smith

Abstract

The asymmetric BODIPY 1 a (BODIPY=4,4-difluoro-4-bora-3a,4a-diaza-s-indacene), containing two chloro substituents at the 3,8-positions and a reactive 5-methyl group, was synthesized from the asymmetric dipyrroketone 3, which was readily obtained from available pyrrole 2 a. The reactivity of 3,8-dichloro-6-ethyl-1,2,5,7-tetramethyl-BODIPY 1 a was investigated by using four types of reactions. This versatile BODIPY undergoes regioselective Pd(0) -catalyzed Stille coupling reactions and/or regioselective nucleophilic addition/elimination reactions, first at the 8-chloro and then at the 3-chloro group, using a variety of organostannanes and N-, O-, and S-centered nucleophiles. On the other hand, the more reactive 5-methyl group undergoes regioselective Knoevenagel condensation with an aryl aldehyde to produce a monostyryl-BODIPY, and oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) gives the corresponding 5-formyl-BODIPY. Investigation of the reactivity of asymmetric BODIPY 1 a led to the preparation of a variety of functionalized BODIPYs with λmax of absorption and emission in the ranges 487-587 and 521-617 nm, respectively. The longest absorbing/emitting compound was the monostyryl-BODIPY 16, and the largest Stokes ...Continue Reading

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Citations

Feb 6, 2016·Journal of Medicinal Chemistry·Sunting XuanM Graça H Vicente
Feb 6, 2017·The Journal of Organic Chemistry·Sunting XuanM Graça H Vicente
Feb 25, 2017·The Journal of Organic Chemistry·Ning ZhaoM Graça H Vicente
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Jun 3, 2016·Organic & Biomolecular Chemistry·Ning ZhaoM Graça H Vicente
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Apr 18, 2017·Bioconjugate Chemistry·Ning ZhaoM Graça H Vicente
May 19, 2018·The Journal of Organic Chemistry·Andrea SavoldelliM Graça H Vicente

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