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. 2019 Jan 7:15:67-71.
doi: 10.3762/bjoc.15.7. eCollection 2019.

Gold-catalyzed ethylene cyclopropanation

Silvia G Rull  1 , Andrea Olmos  1 , Pedro J Pérez  1
Affiliations

Gold-catalyzed ethylene cyclopropanation

Silvia G Rull et al. Beilstein J Org Chem. .

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/NaBArF 4 (IPr = 1,3-bis(2,6-diisopropylphenyl)imidazole-2-ylidene; BArF 4 = tetrakis(3,5-bis(trifluoromethyl)phenyl)borate).

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

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Figures

Scheme 1
Scheme 1
(a) General metal-catalyzed olefin cyclopropanation reaction with diazo compounds. (b) The ethylene cyclopropanation with diazoacetates leads to cyclopropanecarboxylates.
Scheme 2
Scheme 2
Routes toward ethyl cyclopropanecarboxylate (1). (a) Ethylene cyclopropanation described by De Bruin and co-workers as secondary reaction. (b) Stoichiometric transformations. (c) Gold-catalyzed ethylene cyclopropanation described in this work.
Figure 1
Figure 1
Effect of the pressure of ethylene on the yields of ethyl cyclopropanecarboxylate in the reaction of ethylene and EDA catalyzed by IPrAuCl/NaBArF4.
See this image and copyright information in PMC

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