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芳基化策略，可在二氟化硼二吡咯甲烷（boron dipyrromethenes, BODIPY）的2,6-位进行反应，作为后期修饰手段快速构建多样性导向的BODIPY文库。该方案的补充完善，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种新型吲哚稠合BODIPY，该化合物展现出明亮的红光/近红外荧光，具备较大的摩尔消光系数（145 500 M–1 cm–1）与较高的量子产率（71%）。