Organophosphane-catalyzed direct β-acylation of 4-arylidene pyrazolones and 5-arylidene thiazolones with acyl chlorides

Pankaj V. Khairnar; Yin Hsiang Su; Yung Chang Chen; Athukuri Edukondalu; Yi Ru Chen; Wenwei Lin

doi:10.1021/acs.orglett.0c02408

Organophosphane-catalyzed direct β-acylation of 4-arylidene pyrazolones and 5-arylidene thiazolones with acyl chlorides

Pankaj V. Khairnar, Yin Hsiang Su, Yung Chang Chen, Athukuri Edukondalu, Yi Ru Chen, Wenwei Lin^*

^*此作品的通信作者

化學系

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

13 引文斯高帕斯（Scopus）

摘要

An efficient method for the direct β-acylation of arylidene pyrazolones and thiazolones with acyl chlorides in the presence of a base catalyzed by organophosphanes is reported. A variety of functionalized 4-arylidene pyrazolone and 5-arylidene thiazolone derivatives were prepared under metal-free and mild conditions via a tandem phospha-Michael addition/O-acylation/intramolecular cyclization/rearrangement sequence. Our mechanistic investigations revealed that the reaction is highly stereospecific to provide exclusively cis-isomers, and the methodology can also be scaled up with similar efficacy.

原文	英語
頁（從 - 到）	6868-6872
頁數	5
期刊	Organic Letters
卷	22
發行號	17
DOIs	https://doi.org/10.1021/acs.orglett.0c02408
出版狀態	已發佈 - 2020 9月 4

ASJC Scopus subject areas

生物化學
物理與理論化學
有機化學

存取文件

10.1021/acs.orglett.0c02408

其它文件與鏈接

CCDC 2006528: Experimental Crystal Structure Determination
Khairnar, P. V. (Contributor), Su, Y. (Contributor), Chen, Y. (Contributor), Edukondalu, A. (Contributor), Chen, Y. (Contributor) & Lin, W. (Contributor), Unknown Publisher, 2020
DOI: 10.5517/ccdc.csd.cc25byq6, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc25byq6&sid=DataCite
資料集: Dataset
CCDC 1960460: Experimental Crystal Structure Determination
Khairnar, P. V. (Contributor), Su, Y. (Contributor), Chen, Y. (Contributor), Edukondalu, A. (Contributor), Chen, Y. (Contributor) & Lin, W. (Contributor), Unknown Publisher, 2020
DOI: 10.5517/ccdc.csd.cc23t0nm, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc23t0nm&sid=DataCite
資料集: Dataset
CCDC 1972709: Experimental Crystal Structure Determination
Khairnar, P. V. (Contributor), Su, Y. (Contributor), Chen, Y. (Contributor), Edukondalu, A. (Contributor), Chen, Y. (Contributor) & Lin, W. (Contributor), Unknown Publisher, 2020
DOI: 10.5517/ccdc.csd.cc246rsx, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc246rsx&sid=DataCite
資料集: Dataset

引用此

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title = "Organophosphane-catalyzed direct β-acylation of 4-arylidene pyrazolones and 5-arylidene thiazolones with acyl chlorides",

abstract = "An efficient method for the direct β-acylation of arylidene pyrazolones and thiazolones with acyl chlorides in the presence of a base catalyzed by organophosphanes is reported. A variety of functionalized 4-arylidene pyrazolone and 5-arylidene thiazolone derivatives were prepared under metal-free and mild conditions via a tandem phospha-Michael addition/O-acylation/intramolecular cyclization/rearrangement sequence. Our mechanistic investigations revealed that the reaction is highly stereospecific to provide exclusively cis-isomers, and the methodology can also be scaled up with similar efficacy.",

author = "Khairnar, {Pankaj V.} and Su, {Yin Hsiang} and Chen, {Yung Chang} and Athukuri Edukondalu and Chen, {Yi Ru} and Wenwei Lin",

note = "Publisher Copyright: Copyright {\textcopyright} 2020 American Chemical Society.",

year = "2020",

month = sep,

day = "4",

doi = "10.1021/acs.orglett.0c02408",

language = "English",

volume = "22",

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T1 - Organophosphane-catalyzed direct β-acylation of 4-arylidene pyrazolones and 5-arylidene thiazolones with acyl chlorides

AU - Khairnar, Pankaj V.

AU - Su, Yin Hsiang

AU - Chen, Yung Chang

AU - Edukondalu, Athukuri

AU - Chen, Yi Ru

AU - Lin, Wenwei

PY - 2020/9/4

Y1 - 2020/9/4

N2 - An efficient method for the direct β-acylation of arylidene pyrazolones and thiazolones with acyl chlorides in the presence of a base catalyzed by organophosphanes is reported. A variety of functionalized 4-arylidene pyrazolone and 5-arylidene thiazolone derivatives were prepared under metal-free and mild conditions via a tandem phospha-Michael addition/O-acylation/intramolecular cyclization/rearrangement sequence. Our mechanistic investigations revealed that the reaction is highly stereospecific to provide exclusively cis-isomers, and the methodology can also be scaled up with similar efficacy.

AB - An efficient method for the direct β-acylation of arylidene pyrazolones and thiazolones with acyl chlorides in the presence of a base catalyzed by organophosphanes is reported. A variety of functionalized 4-arylidene pyrazolone and 5-arylidene thiazolone derivatives were prepared under metal-free and mild conditions via a tandem phospha-Michael addition/O-acylation/intramolecular cyclization/rearrangement sequence. Our mechanistic investigations revealed that the reaction is highly stereospecific to provide exclusively cis-isomers, and the methodology can also be scaled up with similar efficacy.

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Organophosphane-catalyzed direct β-acylation of 4-arylidene pyrazolones and 5-arylidene thiazolones with acyl chlorides

摘要

ASJC Scopus subject areas

存取文件

其它文件與鏈接

指紋

資料集

CCDC 2006528: Experimental Crystal Structure Determination

CCDC 1960460: Experimental Crystal Structure Determination

CCDC 1972709: Experimental Crystal Structure Determination

引用此