Isoindolinones via Copper-Catalyzed Intramolecular Benzylic C-H Sulfamidation

Robin Bedford, John G Bowen, Carolina Méndez-Gálvez

Research output: Contribution to journalArticle (Academic Journal)peer-review

23 Citations (Scopus)
203 Downloads (Pure)

Abstract

2-Benzyl-N-tosylbenzamides and related substrates undergo copper-catalyzed intramolecular sulfamidation at the ben-zylic methylene to give N-arylsuflonyl-1-arylisoindolinones, which can be N-deprotected using samarium iodide to generate the free 1-arylisoindolinones. Preliminary mechanistic studies indicate that the rate-determining step is not C-H bond cleavage, but are instead consistent with slow oxidation of a copper π-arene intermediate.
Original languageEnglish
Pages (from-to)1719-1725
Number of pages7
JournalJournal of Organic Chemistry
Volume82
Issue number3
Early online date13 Jan 2017
DOIs
Publication statusPublished - 3 Feb 2017

Keywords

  • Copper
  • C-H activation
  • amidation
  • sulfamidation

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