Synthesis of triphenylene-fused phosphole oxides via C – H functionalizations

Abstract
The synthesis of triphenylene-fused phosphole oxides has been achieved through two distinct C–H functionalization reactions as key steps. The phosphole ring was constructed by a three-component coupling of 3-(methoxymethoxy)phenylzinc chloride, an alkyne, and dichlorophenylphosphine, involving the regioselective C–H activation of the C2 position of the arylzinc intermediate via 1,4-cobalt migration. The resulting 7-hydroxybenzo[b]phosphole derivative was used for further π-extension through Suzuki–Miyaura couplings and a Scholl reaction, the latter closing the triphenylene ring. The absorption and emission spectra of the thus-synthesized compounds illustrated their nature as hybrids of triphenylene and benzo[b]phosphole.

Beilstein J. Org. Chem. 2020, 16, 524–529. doi:10.3762/bjoc.16.48

Source: Beilstein Journal of Organic Chemistry - March 26, 2020 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: C – H functionalization fluorescence phosphole polycyclic aromatic hydrocarbons triphenylene Letter Source Type: research