Catalytic amide base system generatedin situfor 1,3-diene formation from allylbenzenes and carbonyls

Masanori Shigeno, Akihisa Kajima, Kunihito Nakaji, Kanako Nozawa-Kumada, Yoshinori Kondo

Research output: Contribution to journalArticlepeer-review

Abstract

The amide base generatedin situfrom tetramethylammonium fluoride and N(TMS)3catalyzes the synthesis of 1,3-diene from an allylbenzene and carbonyl compound. The system is applicable to the transformations of a variety of allylbenzenes with functional groups (halogen, methyl, phenyl, methoxy, dimethylamino, ester, and amide moieties). Acyclic and cyclic diaryl ketones, pivalophenone, pivalaldehyde, and isobutyrophenone are used as coupling partners. The role oftransβ-methyl stilbenes in product formation is also elucidated.

Original languageEnglish
Pages (from-to)983-987
Number of pages5
JournalOrganic and Biomolecular Chemistry
Volume19
Issue number5
DOIs
Publication statusPublished - 2021 Feb 7

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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