A cascade Suzuki-Miyaura/Diels-Alder protocol: exploring the bifunctional utility of vinyl Bpin

David L. Cain, Calum McLaughlin, John Molloy, Cameron Carpenter-Warren, Niall A. Anderson, Allan J. B. Watson

Research output: Contribution to journalArticlepeer-review

15 Citations (Scopus)
8 Downloads (Pure)

Abstract

Cascade reactions are an important strategy in reaction design, allowing streamlining of chemical synthesis. Here we report a cascade Suzuki-Miyaura/Diels-Alder reaction, employing vinyl Bpin as a bifunctional reagent in two distinct roles: as an organoboron nucleophile for cross- coupling and as a Diels-Alder dienophile. Merging these two reactions enables a rapid and operationally simple synthesis of functionalized carbocycles in good yield. The effect of the organoboron subtype on Diels- Alder regioselectivity was investigated and post-synthetic modifications were carried out on a model substrate. The potential for a complementary Heck/Diels-Alder process was also assessed.
Original languageEnglish
Pages (from-to)787-791
Number of pages5
JournalSynlett
Volume30
Issue number7
Early online date24 Oct 2018
DOIs
Publication statusPublished - Apr 2019

Keywords

  • Bpin
  • Cascade
  • Cross-coupling
  • Diels-Alder
  • Suzuki-Miyaura

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