Catalytic Deprotonative α‑Formylation of Heteroarenes by an Amide Base Generated in Situ from Tetramethylammonium Fluoride and Tris(trimethylsilyl)amine

Catalytic Deprotonative α‑Formylation of Heteroarenes by an Amide Base Generated in Situ from Tetramethylammonium Fluoride and Tris(trimethylsilyl)amine

Heteroarene formylations in DMF solution proceed in the presence of an amide base catalyst generated in situ from tetramethylammonium fluoride (TMAF) and tris­(trimethylsilyl)­amine (N­(TMS)3). The reaction proceeds at room temperature and has an operationally simple procedure. Various heteroarenes,...

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Veröffentlicht in:Organic process research & development 2019-04, Vol.23 (4), p.443-451
Hauptverfasser: Shigeno, Masanori, Fujii, Yuki, Kajima, Akihisa, Nozawa-Kumada, Kanako, Kondo, Yoshinori
Format: Artikel
Sprache:eng
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Zusammenfassung:Heteroarene formylations in DMF solution proceed in the presence of an amide base catalyst generated in situ from tetramethylammonium fluoride (TMAF) and tris­(trimethylsilyl)­amine (N­(TMS)3). The reaction proceeds at room temperature and has an operationally simple procedure. Various heteroarenes, including benzothiophene, thiophene, benzothiazole, oxazole, and indole derivatives, can be formylated with high functional group tolerance.
ISSN:1083-6160
1520-586X
DOI:10.1021/acs.oprd.8b00247