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Site-Selective C-H Oxygenation via Aryl Sulfonium Salts.

ABSTRACT: Herein, we report a two-step process forming arene C-O bonds in excellent site-selectivity at a late-stage. The C-O bond formation is achieved by selective introduction of a thianthrenium group, which is then converted into C-O bonds using photoredox chemistry. Electron-rich, -poor and -neutral arenes as well as complex drug-like small molecules are successfully transformed into both phenols and various ethers. The sequence differs conceptually from all previous arene oxygenation reactions in that oxygen functionality can be incorporated into complex small molecules at a late stage site-selectively, which has not been shown via aryl halides.

SUBMITTER: Sang R

PROVIDER: S-EPMC7754133 | biostudies-literature | 2019 Nov

REPOSITORIES: biostudies-literature

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Site-Selective C-H Oxygenation via Aryl Sulfonium Salts.

Sang Ruocheng R Korkis Stamatis E SE Su Wanqi W Ye Fei F Engl Pascal S PS Berger Florian F Ritter Tobias T

Angewandte Chemie (International ed. in English) 20190924 45

Herein, we report a two-step process forming arene C-O bonds in excellent site-selectivity at a late-stage. The C-O bond formation is achieved by selective introduction of a thianthrenium group, which is then converted into C-O bonds using photoredox chemistry. Electron-rich, -poor and -neutral arenes as well as complex drug-like small molecules are successfully transformed into both phenols and various ethers. The sequence differs conceptually from all previous arene oxygenation reactions in th ...[more]

PMID: 31475767

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