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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 ?-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.

SUBMITTER: Rahman MS

PROVIDER: S-EPMC7113549 | biostudies-literature | 2020

REPOSITORIES: biostudies-literature

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

Rahman Md Shafiqur MS Yoshikai Naohiko N

Beilstein journal of organic chemistry 20200327

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[<i>b</i>]phosphole derivative was used for further π-extension throu ...[more]

PMID: 32273913

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