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

doi:10.1021/acs.orglett.9b03116

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

Department of Chemistry

Research output: Contribution to journal › Article

3 Citations (Scopus)

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 language	English
Pages (from-to)	8339-8343
Number of pages	5
Journal	Organic Letters
Volume	21
Issue number	20
DOIs	https://doi.org/10.1021/acs.orglett.9b03116
Publication status	Published - 2019 Oct 18

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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Liou, Y. C., Su, Y. H., Ku, K. C., Edukondalu, A., Lin, C. K., Ke, Y. S., Karanam, P., Lee, C. J., & Lin, W. (2019). Organophosphane-Promoted Synthesis of Functionalized α,β-Unsaturated Alkenes and Furanones via Direct β-Acylation. Organic Letters, 21(20), 8339-8343. https://doi.org/10.1021/acs.orglett.9b03116

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 journal › Article

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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.",

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AU - Karanam, Praneeth

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