Regioselective Decarboxylative Direct C–H Arylation of Boron Dipyrromethenes (BODIPYs) at 2,6-Positions: A Facile Access to a Diversity-Oriented BODIPY Library

A palladium-catalyzed regioselective
decarboxylative direct C–H
arylation of boron dipyrromethenes (BODIPYs) at the 2,6-positions
has been developed as a late-stage approach to rapidly assemble a
diversity-oriented BODIPY library. With the complement of this protocol,
the direct C–H arylation of BODIPYs becomes regiocontrollable
at α- and β-positions. A new type of indole-fused BODIPY
exhibiting bright red/NIR fluorescence with a large molar extinction
coefficient (145 500 M–1 cm–1) and a high quantum yield (71%) has been synthesized for the first
time.

本研究开发了一种钯催化的区域选择性脱羧直接C–H芳基化方法，可在二氟化硼二吡咯甲烷（boron dipyrromethenes, BODIPY）的2,6-位进行修饰，作为后期修饰策略快速构建多样性导向的BODIPY化合物库。该方法的补充完善，使得BODIPY的直接C–H芳基化反应可在α位与β位实现区域可控。本研究首次合成了一类新型吲哚稠合BODIPY，该类化合物展现出明亮的红光/近红外荧光特性，其摩尔消光系数可达145500 M–1 cm–1，量子产率高达71%。