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Monatshefte für Chemie - Chemical Monthly

, Volume 150, Issue 2, pp 295–302 | Cite as

Copper-catalyzed conjugate addition of in situ formed alkyl boranes to α,β-unsaturated ketones

  • Bernard Mravec
  • Kristína Plevová
  • Radovan ŠebestaEmail author
Original Paper
First Online:
  • 57 Downloads

Abstract

Conjugate addition of in situ formed organometallic reagents to α,β-unsaturated carbonyl compounds provides an efficient way to generate new C–C bonds. We show optimization of the copper-catalyzed conjugate addition of alkylboranes, which were formed directly in the reaction mixture by hydroboration of alkenes. We have improved the reaction conditions by employing “greener”, less hygroscopic, and higher boiling solvent, 2-methyltetrahydrofuran. We have also broadened the scope of the reaction. Furthermore, chiral ferrocenyl carbene ligands were assessed in the enantioselective version of the transformation with medium enantioselectivity 67:33 e.r.

Graphical abstract

Keywords

Cu catalysis Conjugate addition Organoborane Hydroboration 2-Methyltetrahydrofuran 
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Notes

Acknowledgements

This work was supported by the Slovak Research and Development Agency under contract no. APVV-0321-12.

Supplementary material

706_2018_2309_MOESM1_ESM.docx (3.3 mb)
Supplementary material 1 (DOCX 3417 kb)

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© Springer-Verlag GmbH Austria, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Department of Organic Chemistry, Faculty of Natural SciencesComenius University in BratislavaBratislavaSlovakia

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