Document Detail


Synthesis of symmetrical and unsymmetrical diarylalkynes from propiolic acid using palladium-catalyzed decarboxylative coupling.
MedLine Citation:
PMID:  20795634     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
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.
Authors:
Kyungho Park; Goun Bae; Jeongju Moon; Jaehoon Choe; Kwang Ho Song; Sunwoo Lee
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  75     ISSN:  1520-6904     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2010 Sep 
Date Detail:
Created Date:  2010-09-10     Completed Date:  2011-01-11     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  6244-51     Citation Subset:  IM    
Affiliation:
Department of Chemistry, Chonnam National University, 300 Yongbong-dong, Buk-gu, Gwangju 500-757, Republic of Korea.
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MeSH Terms
Descriptor/Qualifier:
Alkynes / chemical synthesis*,  chemistry
Catalysis
Decarboxylation
Fatty Acids, Unsaturated / chemistry
Molecular Structure
Organometallic Compounds / chemistry*
Palladium / chemistry*
Propionates / chemistry*
Stereoisomerism
Chemical
Reg. No./Substance:
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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