Gold-catalyzed ethylene cyclopropanation

Silvia G Rull; Andrea Olmos; Pedro J Pérez

doi:10.3762/bjoc.15.7

Gold-catalyzed ethylene cyclopropanation

Beilstein J Org Chem. 2019 Jan 7:15:67-71. doi: 10.3762/bjoc.15.7. eCollection 2019.

Authors

Silvia G Rull¹, Andrea Olmos¹, Pedro J Pérez¹

Affiliation

¹ Laboratorio de Catálisis Homogénea, Unidad Asociada al CSIC, CIQSO-Centro de Investigación en Química Sostenible and Departamento de Química, Universidad de Huelva, Campus de El Carmen 21007 Huelva, Spain.

Abstract

Ethylene can be directly converted into ethyl 1-cyclopropylcarboxylate upon reaction with ethyl diazoacetate (N₂CHCO₂Et, EDA) in the presence of catalytic amounts of IPrAuCl/NaBAr^F ₄ (IPr = 1,3-bis(2,6-diisopropylphenyl)imidazole-2-ylidene; BAr^F ₄ = tetrakis(3,5-bis(trifluoromethyl)phenyl)borate).

Keywords: carbene transfer; cyclopropane; cyclopropylcarboxylate; ethyl diazoacetate; ethylene cyclopropanation; gold catalysis.