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

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

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ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Cite this

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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10.1021/acs.orglett.9b03116