Carbon–Carbon Bond Activation with 8-Acylquinolines

Ashley M. Dreis, Christopher J. Douglas

Research output: Contribution to journalArticlepeer-review

15 Scopus citations


Synthetically relevant advances in the area of carbon-carbon sigma bond activation have been made possible by 8-acylquinoline directing groups. Stable rhodium metallacycle intermediates have been shown to undergo a variety of transformations, including carboacylation reactions, to produce value-added products containing all-carbon quaternary centers. The kinetic profile of such reactions has been shown to be substrate dependent.

Original languageEnglish (US)
Pages (from-to)85-110
Number of pages26
JournalTopics in Current Chemistry
StatePublished - 2014

Bibliographical note

Funding Information:
The authors thank the National Science Foundation (CHE-115157), the donors of the Petroleum Research Fund (47565-G1), and Research Corporation for Science Advancement (Cottrell Scholar Award to CJD, 19985) for support of the work in this chapter carried out at Minnesota.

Publisher Copyright:
© Springer-Verlag Berlin Heidelberg 2014.


  • 8-Acylquinoline
  • 8-Quinolinyl ketone
  • All-carbon quaternary centers
  • Bond insertion
  • Carboacylation
  • Carbon–carbon bond activation
  • Chelation
  • Cyclometalation
  • Directed metalation
  • Directing group
  • Metallacycle
  • Oxidative addition
  • Rhodium catalyst


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