Organic superbase t-Bu-P4-catalyzed demethylations of methoxyarenes

Masanori Shigeno, Kazutoshi Hayashi, Toshinobu Korenaga, Kanako Nozawa-Kumada, Yoshinori Kondo

Research output: Contribution to journalArticlepeer-review

Abstract

Herein, we report that the organic superbase t-Bu-P4 catalyzes the demethylation reactions of methoxyarenes in the presence of alkanethiol and hexamethyldisilazane. The system can efficiently convert a variety of substrates, including electron-deficient, -neutral, and -rich substrates and heteroaromatic substrates, and displays excellent functional group tolerance. Computational studies show that the high reactivity achieved by t-Bu-P4 is due to the formation of the nucleophilic naked thiolate species.

Original languageEnglish
Pages (from-to)3656-3663
Number of pages8
JournalOrganic Chemistry Frontiers
Volume9
Issue number14
DOIs
Publication statusPublished - 2022 May 9

ASJC Scopus subject areas

  • Organic Chemistry

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