Selective C-H bond hydroxylation of cyclohexanes in water by supramolecular control

Bin Yang, Jian Fang Cui, Man Kin Wong

Research output: Journal article publicationJournal articleAcademic researchpeer-review

2 Citations (Scopus)

Abstract

A new approach for selective hydroxylation of non-activated cyclohexanes using dioxirane generated in situ in water through supramolecular control has been developed. Using β-CD and γ-CD as the supramolecular hosts, selective hydroxylation of cyclohexane substrates, including trans/cis-1,4-, 1,3-and 1,2-dimethylcyclohexanes and trans/cis-decahydronaphthalene, was achieved in up to 54% yield in water. Furthermore, site-selective C-H bond hydroxylation of (+)-menthol was achieved by obstructing the approach of dioxirane to the C-H bond with higher steric hindrance through inclusion complexation with β-CD and γ-CD in water.
Original languageEnglish
Pages (from-to)30886-30893
Number of pages8
JournalRSC Advances
Volume7
Issue number49
DOIs
Publication statusPublished - 1 Jan 2017

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

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