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Title: Synthesis of triphenylene-fused phosphole oxides via C-H functionalizations
Authors: Md. Shafiqur Rahman
Yoshikai, Naohiko
Keywords: Science::Chemistry
Issue Date: 2020
Source: Md. Shafiqur Rahman & Yoshikai, N. (2020). Synthesis of triphenylene-fused phosphole oxides via C-H functionalizations. Beilstein Journal of Organic Chemistry, 16, 524-529.
Project: MOE2016-T2-2-043
Journal: Beilstein Journal of Organic Chemistry
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.
ISSN: 1860-5397
DOI: 10.3762/bjoc.16.48
Schools: School of Physical and Mathematical Sciences 
Rights: © 2020 The Author(s). This is an Open Access article under the terms of the Creative Commons Attribution License ( Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited.The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (
Fulltext Permission: open
Fulltext Availability: With Fulltext
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