Silver Triflate Catalyzed Cyclopropyl Carbinol Rearrangement for Benzo[b]oxepine and 2H-Chromene Synthesis

Philip Wai Hong Chan, Wan Teng Teo, Shaun Wei Yong Koh, Bo Ra Lee, Benjamin James Ayers, Dik-Lung Edmond Ma, Chung-Hang Duncan Leung

Research output: Contribution to journalArticleResearchpeer-review

11 Citations (Scopus)

Abstract

An efficient AgOTf-catalyzed (TfO = trifluoromethanesulfonate) cyclopropyl carbinol rearrangement for the synthesis of benzo[b]oxepines and 2H-chromenes is reported by starting from 2-[cyclopropyl(hydroxy)methyl]phenols. The reactions proved to be general in scope and furnished a range of the corresponding functionalized oxygen heterocycles. The formation of the benzo-fused six-membered adduct is proposed to result from the ring-contraction of the benzo[b]oxepine derivative. Control of the product selectivity is achievable by fine-tuning the reaction time. The catalytic synergy between the silver(I) cation and the triflate anion was essential for optimal product yields. An efficient AgOTf-catalyzed (TfO = trifluoromethanesulfonate) cyclopropyl carbinol rearrangement to prepare benzo[b]oxepines and 2H-chromenes has been developed by starting from [cyclopropyl(hydroxy)methyl]phenols. A catalytic synergy was observed between the silver(I) cation and the triflate anion, which furnished the functionalized oxygen heterocycles.

Original languageEnglish
Pages (from-to)4447-4456
Number of pages10
JournalEuropean Journal of Organic Chemistry
Volume2015
Issue number20
DOIs
Publication statusPublished - 1 Jul 2015

Keywords

  • Homogeneous catalysis
  • Oxygen heterocycles
  • Rearrangement
  • Ring expansion
  • Silver

Cite this

Chan, Philip Wai Hong ; Teo, Wan Teng ; Koh, Shaun Wei Yong ; Lee, Bo Ra ; Ayers, Benjamin James ; Ma, Dik-Lung Edmond ; Leung, Chung-Hang Duncan. / Silver Triflate Catalyzed Cyclopropyl Carbinol Rearrangement for Benzo[b]oxepine and 2H-Chromene Synthesis. In: European Journal of Organic Chemistry. 2015 ; Vol. 2015, No. 20. pp. 4447-4456.
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abstract = "An efficient AgOTf-catalyzed (TfO = trifluoromethanesulfonate) cyclopropyl carbinol rearrangement for the synthesis of benzo[b]oxepines and 2H-chromenes is reported by starting from 2-[cyclopropyl(hydroxy)methyl]phenols. The reactions proved to be general in scope and furnished a range of the corresponding functionalized oxygen heterocycles. The formation of the benzo-fused six-membered adduct is proposed to result from the ring-contraction of the benzo[b]oxepine derivative. Control of the product selectivity is achievable by fine-tuning the reaction time. The catalytic synergy between the silver(I) cation and the triflate anion was essential for optimal product yields. An efficient AgOTf-catalyzed (TfO = trifluoromethanesulfonate) cyclopropyl carbinol rearrangement to prepare benzo[b]oxepines and 2H-chromenes has been developed by starting from [cyclopropyl(hydroxy)methyl]phenols. A catalytic synergy was observed between the silver(I) cation and the triflate anion, which furnished the functionalized oxygen heterocycles.",
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Silver Triflate Catalyzed Cyclopropyl Carbinol Rearrangement for Benzo[b]oxepine and 2H-Chromene Synthesis. / Chan, Philip Wai Hong; Teo, Wan Teng; Koh, Shaun Wei Yong; Lee, Bo Ra; Ayers, Benjamin James; Ma, Dik-Lung Edmond; Leung, Chung-Hang Duncan.

In: European Journal of Organic Chemistry, Vol. 2015, No. 20, 01.07.2015, p. 4447-4456.

Research output: Contribution to journalArticleResearchpeer-review

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AU - Ayers, Benjamin James

AU - Ma, Dik-Lung Edmond

AU - Leung, Chung-Hang Duncan

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