| Synthesis of symmetrical and unsymmetrical diarylalkynes from propiolic acid using palladium-catalyzed decarboxylative coupling. | |
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MedLine Citation:
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PMID: 20795634 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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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(PPh(3))(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 °C. The coupling reaction showed tolerance for functional groups such as ester, ketone, and aldehyde and exhibited chemoselectivity. In the coupling reaction of propiolic acid with aryl bromide, the diarylated product was the major one at 80 °C, even though 1 equiv of aryl halides was employed. However, among the monoarylated products that were formed predominantly at 25 and 50 °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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Authors:
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Kyungho Park; Goun Bae; Jeongju Moon; Jaehoon Choe; Kwang Ho Song; Sunwoo Lee |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: The Journal of organic chemistry Volume: 75 ISSN: 1520-6904 ISO Abbreviation: J. Org. Chem. Publication Date: 2010 Sep |
Date Detail:
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Created Date: 2010-09-10 Completed Date: 2011-01-11 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: United States |
Other Details:
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Languages: eng Pagination: 6244-51 Citation Subset: IM |
Affiliation:
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Department of Chemistry, Chonnam National University, 300 Yongbong-dong, Buk-gu, Gwangju 500-757, Republic of Korea. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Alkynes
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chemical synthesis*,
chemistry Catalysis Decarboxylation Fatty Acids, Unsaturated / chemistry Molecular Structure Organometallic Compounds / chemistry* Palladium / chemistry* Propionates / chemistry* Stereoisomerism |
| Chemical | |
Reg. No./Substance:
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0/Alkynes; 0/Fatty Acids, Unsaturated; 0/Organometallic Compounds; 0/Propionates; 142-45-0/2-butynedioic acid; 471-25-0/propiolic acid; 7440-05-3/Palladium |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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