Department of Chemistry, Dalhousie University , Halifax, NS B3H 4R2, Canada.
Department of Chemistry, Saint Mary's University , Halifax, NS B3H 3C3, Canada.
J Org Chem. 2017 Jul 7;82(13):7059-7064. doi: 10.1021/acs.joc.7b01129. Epub 2017 Jun 24.
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·OEt and NEt 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.
一种具有共轭末端炔基取代基的不对称介孔 H 二吡咯被转化为其相应的二氟硼配合物,并通过 Sonogashira 交叉偶联进一步扩展了π-共轭。用 BF·OEt 和 NEt 处理炔基取代的二吡咯,揭示了共轭末端炔基对路易斯活化亲电取代的反应性,并导致末端溴乙烯基和烯醇取代基的 F-BODIPY 的分离。