Publication:
Copper/Persulfate-Promoted Oxidative Decarboxylative C−H Acylation of Pyrazolones with α-Oxocarboxylic Acids: Direct Access to 4-Acylpyrazolones under Mild Conditions

Issued Date

2018-09-03

Resource Type

Article

ISSN

16154169
16154150

DOI

10.1002/adsc.201800464

Other identifier(s)

2-s2.0-85052674526

Rights

Mahidol University

Rights Holder(s)

SCOPUS

Bibliographic Citation

Advanced Synthesis and Catalysis. Vol.360, No.17 (2018), 3345-3355

Suggested Citation

Tanakorn Kittikool, Akkharaphong Thupyai, Khamphee Phomphrai, Sirilata Yotphan Copper/Persulfate-Promoted Oxidative Decarboxylative C−H Acylation of Pyrazolones with α-Oxocarboxylic Acids: Direct Access to 4-Acylpyrazolones under Mild Conditions. Advanced Synthesis and Catalysis. Vol.360, No.17 (2018), 3345-3355. doi:10.1002/adsc.201800464 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/45419

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Title

Copper/Persulfate-Promoted Oxidative Decarboxylative C−H Acylation of Pyrazolones with α-Oxocarboxylic Acids: Direct Access to 4-Acylpyrazolones under Mild Conditions

Author(s)

Tanakorn Kittikool
 Akkharaphong Thupyai
 Khamphee Phomphrai
 Sirilata Yotphan

Other Contributor(s)

Vidyasirimedhi Institute of Science and Technology
 Mahidol University

Abstract

© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim A facile and efficient oxidative C−H acylation of N-substituted pyrazolones using α-oxocarboxylic acids as an acyl group source was developed. A combination of Cu(OAc)2 and K2S2O8 enables the reaction to proceed smoothly under air and provides a wide array of 4-acylpyrazolone products in moderate to excellent yields. The mechanism of this transformation is believed to proceed via a copper-induced decarboxylation to form the acyl-copper species. This method provides a convenient and useful route for a direct installation of an acyl moiety into bioactive pyrazolone derivatives, which can be further utilized in many applications. (Figure presented.).

Keyword(s)

Chemical Engineering
 Chemistry

Availability

URI

https://repository.li.mahidol.ac.th/handle/20.500.14594/45419

Collections

Scopus 2018