Ionic Thiourea Organocatalysis of the Morita–Baylis–Hillman Reaction

Trevor McGrath; Katherine N. Robertson; Jason D. Masuda; Jason A. C. Clyburne; Robert D. Singer

doi:10.1071/CH15596

RESEARCH ARTICLE

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Ionic Thiourea Organocatalysis of the Morita–Baylis–Hillman Reaction

Trevor McGrath ^A , Katherine N. Robertson ^A , Jason D. Masuda ^A , Jason A. C. Clyburne ^A and Robert D. Singer ^A ^B

+ Author Affiliations

- Author Affiliations

^A Atlantic Centre for Green Chemistry, Department of Chemistry, Saint Mary's University, Halifax, Nova Scotia, Canada.

^B Corresponding author. Email: robert.singer@smu.ca

Australian Journal of Chemistry 69(7) 759-762 https://doi.org/10.1071/CH15596
Submitted: 23 September 2015 Accepted: 23 November 2015 Published: 28 January 2016

Abstract

An ionic thiourea based organocatalyst has been shown to promote a 1,4-diazabicyclo[2.2.2]octane, (DABCO) catalysed Morita-Baylis-Hillman reaction between benzaldehyde and cyclohex-2-en-1-one. The ionic thiourea catalyst was easily prepared from a pyrrolidinium salt containing an arylamine moiety and 3,5-di(trifluoromethyl)phenylisothiocyanate. X-ray crystallographic analysis of the ionic thiourea catalyst shows an acetone molecule doubly hydrogen bonded to the Lewis acidic thiourea N-H protons. Entrainment of the ionic thiourea co-catalyst in the ionic liquid N-butyl-N-methylpyrrolidinium bistriflimide, [BMPyr][N(Tf)₂], facilitates catalyst recycling and affords very good yields with reaction times reduced through use of microwave heating.

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Ionic Thiourea Organocatalysis of the Morita–Baylis–Hillman Reaction

Abstract

References

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