Gold(I)-catalyzed synthesis of 3-sulfenyl pyrroles and indoles by a regioselective annulation of alkynyl thioethers

Research output: Contribution to journalLetterpeer-review

Authors

Colleges, School and Institutes

External organisations

  • ELI LILLY AND COMPANY

Abstract

The combination of nucleophilic nitrenoids and π-acid catalysis has emerged as a powerful tool in heterocycle synthesis. Accessing more varied heterocycle-substitution patterns by maintaining the same reaction pathways across different alkynes remains a challenge. Here we show that Au(I) catalysis of isoxazole-based nitrenoids with alkynyl thioethers provides controlled access to (3 + 2) annulation by a regioselective addition β to the sulfenyl group. The reaction with isoxazole-containing nitrenoids delivers sulfenylated pyrroles and indoles as single regioisomers bearing useful functional groups and structural variety.

Details

Original languageEnglish
Pages (from-to)6357–6362
Number of pages6
JournalACS Catalysis
Volume11
Early online date13 May 2021
Publication statusE-pub ahead of print - 13 May 2021

Keywords

  • gold, pyrroles, nitrenoid, annulation, thioether, indole