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

J Org Chem. 2017 Jul 7;82(13):7059-7064. doi: 10.1021/acs.joc.7b01129. Epub 2017 Jun 24.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't