Selectively fluorinated cyclohexane building blocks: Derivatives of carbonylated all-cis-3-phenyl-1,2,4,5-tetrafluorocyclohexane

Mohammed Salah Ayoup; David B Cordes; Alexandra M Z Slawin; David O'Hagan

doi:10.3762/bjoc.11.287

Selectively fluorinated cyclohexane building blocks: Derivatives of carbonylated all-cis-3-phenyl-1,2,4,5-tetrafluorocyclohexane

Beilstein J Org Chem. 2015 Dec 21:11:2671-6. doi: 10.3762/bjoc.11.287. eCollection 2015.

Authors

Mohammed Salah Ayoup¹, David B Cordes², Alexandra M Z Slawin², David O'Hagan²

Affiliations

¹ School of Chemistry, University of St Andrews, North Haugh, St Andrews, KY16 9ST, UK; Department of Chemistry, Faculty of Science, P.B 426 Ibrahimia, Alexandria University, Egypt.
² School of Chemistry, University of St Andrews, North Haugh, St Andrews, KY16 9ST, UK.

Abstract

Palladium catalysed carbonylation reactions using the meta- and para-iodo derivatives of all-cis-3-phenyl-1,2,4,5-tetrafluorocyclohexane (4) are illustrated as the start point for a variety of functional group interconversions. The resultant benzaldehyde and benzoic acids offer novel building blocks for further derivatisation and facilitate the incorporation of the facially polarised all-cis-1,2,4,5-tetrafluorocyclohexane motif into more advanced molecular scaffolds.

Keywords: cyclohexane carbonylation; fluorine containing building blocks: organofluorine chemistry.