Dearomatization of 3-cyanoindoles by (3 + 2) cycloaddition: From batch to flow chemistry

Maxime Manneveau, Saori Tanii, Fanny Gens, Julien Legros, Isabelle Chataigner

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

Abstract

1,3-Dipolar dearomatizing cycloadditions between a non-stabilized azomethine ylide and 3-cyanoindoles or benzofuran afford the corresponding 3D-heterocycles bearing a quaternary carbon centre at the ring junction. While 6 equivalents of ylide precursor 1 are required for full conversion in a classical flask, working under flow conditions limits the excess (3 equiv., tR = 1 min) and leads to a cleaner process, affording cycloadducts that are easier to isolate.

Original languageEnglish
Pages (from-to)3481-3486
Number of pages6
JournalOrganic and Biomolecular Chemistry
Volume18
Issue number18
DOIs
Publication statusPublished - 2020 May 14

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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