A Palladium(II)-Catalyzed C-H Activation Cascade Sequence for Polyheterocycle Formation

Kevin I. Booker-Milburn*, Steve Cooper

*Corresponding author for this work

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

32 Citations (Scopus)

Abstract

Polyheterocycles are found in many natural products and are useful moieties in functional materials and drug design. As part of a program towards the synthesis of Stemona alkaloids, a novel palladium(II)-catalyzed C-H activation strategy for the construction of such systems has been developed. Starting from simple 1,3-dienyl-substituted heterocycles, a large range of polycyclic systems containing pyrrole, indole, furan and thiophene moieties can be synthesized in a single step. Don't overdo it: A palladium(II)-catalyzed C-H activation cascade sequence for the synthesis of polyheterocycles is reported. Aromatization of the initially formed dihydro species occurred with a quinone oxidant. In some cases the use of one equivalent of the oxidant enabled isolation of the dihydro species as a single isomer (see scheme; X=NMe, O, S).

Original languageEnglish
Pages (from-to)6496-6500
Number of pages5
JournalAngewandte Chemie - International Edition
Volume54
Issue number22
DOIs
Publication statusPublished - 1 May 2015

Structured keywords

  • BCS and TECS CDTs

Keywords

  • C-H activation
  • domino reactions
  • heterocycles
  • homogeneous catalysis
  • palladium

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