Late-Stage Functionalization of the Periphery of Oligophenylene Dendrimers with Various Arene Units via Fourfold C-H Borylation

J Org Chem. 2021 Nov 5;86(21):14433-14443. doi: 10.1021/acs.joc.1c01252. Epub 2021 Sep 1.

Abstract

Late-stage functionalization of the periphery of oligophenylene dendrimers was efficiently achieved via site-selective C-H activation of a preconstructed, readily accessible dendron. By fourfold iridium-catalyzed C-H borylation followed by Suzuki-Miyaura cross-coupling, various arene units were introduced into the end points of the 1,3,5-phenylene-based hydrocarbon dendron. Coupling of the modified dendrons with a core unit, such as 2,6-dibromobenzoic acid derivatives, afforded the periphery-functionalized dendrimers that also have an endohedral functionality at the core position.