Organophosphane-Promoted Synthesis of Functionalized α,β-Unsaturated Alkenes and Furanones via Direct β-Acylation

Yan Cheng Liou, Yin Hsiang Su, Kuan Chun Ku, Athukuri Edukondalu, Chun Kai Lin, You Syuan Ke, Praneeth Karanam, Chia Jui Lee, Wenwei Lin

Research output: Contribution to journalArticle

Abstract

We report a phosphine-mediated direct β-acylation of α,β-unsaturated 1,3-diketones with acyl chlorides and a base. Functionalized furanones were also prepared by the reaction of cinnamic acid and acyl chloride according to our protocol via β-acylation. Our studies revealed that α,β-unsaturated 1,3-diketones with an electron-donating group at the second position favor the formation of β-acylated products, whereas those with oxygen, such as anhydrides, favor furanones via an unprecedented C-acylation/cyclization sequence.

Original languageEnglish
Pages (from-to)8339-8343
Number of pages5
JournalOrganic Letters
Volume21
Issue number20
DOIs
Publication statusPublished - 2019 Oct 18

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acylation
Acylation
Alkenes
alkenes
phosphine
Chlorides
synthesis
chlorides
Anhydrides
Cyclization
anhydrides
phosphines
Electrons
Oxygen
acids
oxygen
products
electrons

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Organophosphane-Promoted Synthesis of Functionalized α,β-Unsaturated Alkenes and Furanones via Direct β-Acylation. / Liou, Yan Cheng; Su, Yin Hsiang; Ku, Kuan Chun; Edukondalu, Athukuri; Lin, Chun Kai; Ke, You Syuan; Karanam, Praneeth; Lee, Chia Jui; Lin, Wenwei.

In: Organic Letters, Vol. 21, No. 20, 18.10.2019, p. 8339-8343.

Research output: Contribution to journalArticle

Liou, YC, Su, YH, Ku, KC, Edukondalu, A, Lin, CK, Ke, YS, Karanam, P, Lee, CJ & Lin, W 2019, 'Organophosphane-Promoted Synthesis of Functionalized α,β-Unsaturated Alkenes and Furanones via Direct β-Acylation', Organic Letters, vol. 21, no. 20, pp. 8339-8343. https://doi.org/10.1021/acs.orglett.9b03116
Liou, Yan Cheng ; Su, Yin Hsiang ; Ku, Kuan Chun ; Edukondalu, Athukuri ; Lin, Chun Kai ; Ke, You Syuan ; Karanam, Praneeth ; Lee, Chia Jui ; Lin, Wenwei. / Organophosphane-Promoted Synthesis of Functionalized α,β-Unsaturated Alkenes and Furanones via Direct β-Acylation. In: Organic Letters. 2019 ; Vol. 21, No. 20. pp. 8339-8343.
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