Iridium-Catalysed C-H Borylation of 2-Pyridones; Bisfunctionalisation of CC4

Aurélien Honraedt, Worawat Niwetmarin, Cecilia Gotti, Hugo Rego Campello*, Timothy Gallagher

*Corresponding author for this work

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

2 Citations (Scopus)
179 Downloads (Pure)

Abstract

The high regioselectivity associated with the iridium-catalysed borylation of pyridones has been exploited to provide a very direct and efficient entry to C(10) doubly substituted CC4 variants of cytisine. Two approaches have been evaluated based on (i) C-H activation of cytisine (or an N-substituted derivative) followed by N-alkylation (to enable dimer formation) and (ii) direct C-H activation and borylation of CC4 itself. Both approaches provide access to C(10)-functionalized CC4 derivatives, but direct borylation of CC4 allows for a wider range of functional group interconversions to be tolerated.

Original languageEnglish
Article numberss-2018-t0235-op
Pages (from-to)3420-3429
Number of pages10
JournalSynthesis (Germany)
Volume50
Issue number17
Early online date29 Jun 2018
DOIs
Publication statusPublished - 29 Jun 2018

Keywords

  • 2-pyridone
  • C-H functionalization
  • CC4
  • cytisine
  • iridium-catalyzed borylation

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