Reagent for the Synthesis of gem-Disubstituted Cyclopropanes

Cyclopropanes are important building blocks used in drug discovery research.¹⁾ Incorporation of cyclopropane moiety is known to not only improve metabolic stability and binding to target proteins through the conformation fixation, but also to adjust pKa and lipophilicity.
Cyclopropane-1,1-diboronic acid bis(pinacol) ester (1) can be utilized in the Suzuki-Miyaura coupling with aryl bromides to synthesize tertiary arylcyclopropylboronic esters.²⁾ When aryl moiety is a phenyl group, the tertiary arylcyclopropylboronic esters can be converted to arylcyclopropyltrifluoroborate salts with potassium hydrogenfluoride, and then converted to gem-disubstituted cyclopropanes by the subsequent Suzuki-Miyaura coupling.

Related Products

C3706

Cyclopropane-1,1-diboronic Acid Bis(pinacol) Ester

C2160

Cesium Carbonate

References

• 1) The “Cyclopropyl Fragment” is a Versatile Player that Frequently Appears in Preclinical/Clinical Drug Molecules
  • T. T. Talele, J. Med. Chem. 2016, 59, 8712.
• 2) A Modular Approach to the Synthesis of gem-Disubstituted Cyclopropanes
  • M. R. Harris, H. M. Wisniewska, W. Jiao, X. Wang, J. N. Bradow, Org. Lett. 2018, 20, 2867.

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