Synthesis of 3,3-disubstituted heterocycles by pd-catalyzed arylallylation of unactivated alkenes

David Phillips, Joanne F. M. Hewitt, David J. France*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

Finding new methods of carbon–carbon bond formation is a key goal in expanding current methodology for heterocycle formation. Because of their inherently nonplanar shape, new methods of forming sp3-rich scaffolds are of particular importance. Although there are methods for combining heterocyclization and formation of new sp3–sp3 carbon–carbon bonds, these form the carbon–heteroatom bond rather than a carbon–carbon bond of the heterocycle. Here, we show a new alkene arylallylation reaction that generates a heterocycle with concomitant formation of two new carbon–carbon bonds. Furthermore, we demonstrate that this process occurs through an isohypsic (redox neutral) mechanism. Overall, this carboallylation reaction gives a new route to the synthesis of 3,3-disubstituted heterocycles.
Original languageEnglish
Pages (from-to)8451-8459
Number of pages9
JournalACS Omega
Volume3
Issue number7
DOIs
Publication statusPublished - 31 Jul 2018

Keywords

  • allylation
  • anions
  • catalysts
  • cyclization
  • hetercyclic compounds

Fingerprint

Dive into the research topics of 'Synthesis of 3,3-disubstituted heterocycles by pd-catalyzed arylallylation of unactivated alkenes'. Together they form a unique fingerprint.

Cite this