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Palladium-Catalyzed Decarboxylative Coupling of Alkynyl Carboxylic Acids with Aryl Tosylates

Authors
Lee, Ju-HyeonRaja, Gabriel Charles EdwinYu, SubeenLee, JunseongSong, Kwang HoLee, Sunwoo
Issue Date
9월-2017
Publisher
AMER CHEMICAL SOC
Citation
ACS OMEGA, v.2, no.9, pp.6259 - 6269
Indexed
SCOPUS
Journal Title
ACS OMEGA
Volume
2
Number
9
Start Page
6259
End Page
6269
URI
https://scholar.korea.ac.kr/handle/2021.sw.korea/82429
DOI
10.1021/acsomega.7b01165
ISSN
2470-1343
Abstract
Decarboxylative coupling reactions of alkynyl carboxylic acids with aryl tosylates were developed in the presence of a palladium catalyst. Among the commercially available phosphine ligands, only 1-dicyclohexylphosphino-2-(di-tert-butylphosphino-ethyl) ferrocene (CyPF-tBu) showed good reactivity. The reaction took place smoothly and gave the decarboxylative coupled products in moderate to good yields. This demonstrates the excellent functional group tolerance toward alkyl, alkoxy, fluoro, thiophenyl, ester, and ketone groups. In addition, alkyl-substituted propiolic acids, such as octynoic and hexynoic acids, were coupled with phenyl tosylate to provide the desired products. We found that the electronic properties of the substituents on the phenyl ring in arylpropiolic acids are an important factor. The order of reactivity was found to be aryl iodide > aryl bromide > aryl tosylate > aryl chloride. However, aryl chloride-bearing electron-withdrawing groups showed higher reactivity than those bearing aryl tosylates.
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