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^*

^*Corresponding author for this work

Department of Chemistry

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

16 Citations (Scopus)

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.

Original language	English
Pages (from-to)	6868-6872
Number of pages	5
Journal	Organic Letters
Volume	22
Issue number	17
DOIs	https://doi.org/10.1021/acs.orglett.0c02408
Publication status	Published - 2020 Sept 4

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.0c02408

Cite this

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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",

pages = "6868--6872",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "17",

}

TY - JOUR

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.

UR - https://www.scopus.com/pages/publications/85090478675

UR - https://www.scopus.com/pages/publications/85090478675#tab=citedBy

U2 - 10.1021/acs.orglett.0c02408

DO - 10.1021/acs.orglett.0c02408

M3 - Article

C2 - 32809836

AN - SCOPUS:85090478675

SN - 1523-7060

VL - 22

SP - 6868

EP - 6872

JO - Organic Letters

JF - Organic Letters

IS - 17

ER -

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

Abstract

ASJC Scopus subject areas

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CCDC 1960460: Experimental Crystal Structure Determination

CCDC 1972711: Experimental Crystal Structure Determination

CCDC 1960457: Experimental Crystal Structure Determination

Cite this

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 1960460: Experimental Crystal Structure Determination

CCDC 1972711: Experimental Crystal Structure Determination

CCDC 1960457: Experimental Crystal Structure Determination

Cite this