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^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

13 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

Access to Document

10.1021/acs.orglett.9b03116

Cite this

@article{c3532df31cc14576a6a0c6621f471100,

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

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.",

author = "Liou, {Yan Cheng} and Su, {Yin Hsiang} and Ku, {Kuan Chun} and Athukuri Edukondalu and Lin, {Chun Kai} and Ke, {You Syuan} and Praneeth Karanam and Lee, {Chia Jui} and Wenwei Lin",

note = "Funding Information: We thank the Ministry of Science and Technology of the Republic of China (MOST 107-2628-M-003-001-MY3) for financial support. Publisher Copyright: Copyright {\textcopyright} 2019 American Chemical Society.",

year = "2019",

month = oct,

day = "18",

doi = "10.1021/acs.orglett.9b03116",

language = "English",

volume = "21",

pages = "8339--8343",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "20",

}

TY - JOUR

T1 - Organophosphane-Promoted Synthesis of Functionalized α,β-Unsaturated Alkenes and Furanones via Direct β-Acylation

AU - Liou, Yan Cheng

AU - Su, Yin Hsiang

AU - Ku, Kuan Chun

AU - Edukondalu, Athukuri

AU - Lin, Chun Kai

AU - Ke, You Syuan

AU - Karanam, Praneeth

AU - Lee, Chia Jui

AU - Lin, Wenwei

N1 - Funding Information: We thank the Ministry of Science and Technology of the Republic of China (MOST 107-2628-M-003-001-MY3) for financial support. Publisher Copyright: Copyright © 2019 American Chemical Society.

PY - 2019/10/18

Y1 - 2019/10/18

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=85073108596&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85073108596&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.9b03116

DO - 10.1021/acs.orglett.9b03116

M3 - Article

C2 - 31566385

AN - SCOPUS:85073108596

SN - 1523-7060

VL - 21

SP - 8339

EP - 8343

JO - Organic Letters

JF - Organic Letters

IS - 20

ER -

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

CCDC 1947032: Experimental Crystal Structure Determination

CCDC 1561010: Experimental Crystal Structure Determination

CCDC 1484673: Experimental Crystal Structure Determination

Cite this

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 1947032: Experimental Crystal Structure Determination

CCDC 1561010: Experimental Crystal Structure Determination

CCDC 1484673: Experimental Crystal Structure Determination

Cite this