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Synthesis of Symmetrical and Unsymmetrical Diarylalkynes from Propiolic Acid Using Palladium-Catalyzed Decarboxylative Coupling

Authors
Park, KyunghoBae, GounMoon, JeongjuChoe, JaehoonSong, Kwang HoLee, Sunwoo
Issue Date
17-Sep-2010
Publisher
AMER CHEMICAL SOC
Citation
JOURNAL OF ORGANIC CHEMISTRY, v.75, no.18, pp.6244 - 6251
Indexed
SCIE
SCOPUS
Journal Title
JOURNAL OF ORGANIC CHEMISTRY
Volume
75
Number
18
Start Page
6244
End Page
6251
URI
https://scholar.korea.ac.kr/handle/2021.sw.korea/115675
DOI
10.1021/jo101398a
ISSN
0022-3263
Abstract
Symmetrical diarylalkynes were obtained from propiolic acid (or 2-butynedioic acid) and aryl halides in good yields. The optimized reaction conditions were 2.0 equiv of aryl halide, 1.0 equiv of propiolic acid, 5.0 mol % Pd(PPh3)(2)Cl-2, 10.0 mol % 1,4-bis(diphenylphosphino)butane (dppb), 2.0 equiv of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), and dimethyl sulfoxide (DMSO) as the solvent. The coupling reaction of 2-butynedioic acid with aryl halides required 110 degrees C. The coupling reaction showed tolerance for functional groups such as ester, ketone, and aldehyde and exhibited chemo-selectivity. In the coupling reaction of propiolic acid with aryl bromide, the diarylated product was the major one at 80 degrees C, even though I equiv of aryl halides was employed. However, among the monoarylated products that were formed predominantly at 25 and 50 degrees C in the coupling reaction with aryl iodide, more Sonogashira coupling product was obtained than the decarboxylative coupling product. Unsymmetrical diarylalkynes were also synthesized via this method, in which all reagents, including propiolic acid, aryl iodide, and aryl bromides were added at the beginning of the reaction.
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