Biomimetic aerobic C-H olefination of cyclic enaminones at room temperature: Development toward the synthesis of 1,3,5-trisubstituted benzenes

Yi Yun Yu, Gunda I. Georg

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

Abstract

A green and mild protocol for the dehydrogenative olefination of cyclic enaminones was devised via palladium catalysis at room temperature using oxygen as the terminal oxidant. The synthetic utility of the olefinated cyclic enaminones afforded a series of unique 1,3,5-trisubstituted benzenes via an unanticipated Diels-Alder tandem reaction. The broad substrate scope and good yields achieved with this new protocol provide an alternative pathway for arene functionalization.

Original languageEnglish (US)
Pages (from-to)1359-1369
Number of pages11
JournalAdvanced Synthesis and Catalysis
Volume356
Issue number6
DOIs
StatePublished - Apr 14 2014

Keywords

  • C-H activation
  • arenes
  • cycloaddition
  • olefination
  • palladium

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