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

• Main Authors: Md. Shafiqur Rahman, Yoshikai, Naohiko
• Other Authors: School of Physical and Mathematical Sciences
• Format: Article
• Language: English
• Published: 2021
• Subjects: Science::Chemistry; C–H Functionalization; Fluorescence
• Online Access: https://hdl.handle.net/10356/147003
• Institution: Nanyang Technological University

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.