Brønsted Acid Catalyzed Oxygenative Bimolecular Friedel–Crafts-type Coupling of Ynamides

Dilip V. Patil, Seung Woo Kim, Quynh H. Nguyen, Hanbyul Kim, Shan Wang, Tuan Hoang, Seunghoon Shin

Research output: Contribution to journalArticle

51 Scopus citations

Abstract

A non-metal approach for accessing α-oxo carbene surrogates for a C−C bond-forming bimolecular coupling between ynamides and nucleophilic arenes was developed. This acid-catalyzed coupling features mild temperature, which is critical for the required temporal chemoselectivity among nucleophiles. The scope of nucleophiles includes indoles, pyrroles, anilines, phenols and silyl enolethers. Furthermore, a direct test of SN2′ mechanism has been provided by employing chiral N,N′-dioxides which also enlightens the nature of the intermediates in related metal-catalyzed processes.

Original languageEnglish
Pages (from-to)3670-3674
Number of pages5
JournalAngewandte Chemie - International Edition
Volume56
Issue number13
DOIs
StatePublished - 2017 Jan 1

Keywords

  • Brønsted acid catalysis
  • intermolecular trapping
  • pyridine-N-oxides
  • ynamides
  • α-oxo carbene surrogate

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