Abstract/Details

Copper(I)-catalyzed cross -coupling reactions and their applications


2007 2007

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Abstract (summary)

The scope of our copper(I)-catalyzed synthesis of diaryl acetylenes have been extended to the synthesis of 2 classes of heterocycles; 2-aryl benzo[ b]furans and 2-aryl indoles, by the cross-coupling of aryl acetylenes to 2-iodophenol and 2-iodoaniline, respectively. In addition, we demonstrated the scope of the copper(I) catalysts in catalyzing the cross-coupling of vinyl iodides. The aryl acetylenes and aryl/alkyl thiols were successfully coupled to vinyl iodides to synthesize 1,3-enynes and vinyl sulfides, respectively, using the well-defined copper(I)-complexes based on triphenylphosphine and nitrogen chelating ligand such as phenanthroline and bipyridine. The advantages of these protocols over the conventional copper-based methods are their simplicity, generality, and high functional group tolerances. We also demonstrated improvements of copper-assisted method of CF3 coupling to aryl iodide using metal trifluoroacetate salt, this reaction is not known with palladium chemistry. The possible mechanism of copper(I)-catalyzed reaction is also discussed and the application of our copper(I)-catalyzed protocol to the synthesis of interesting materials in cases where palladium catalyst failed is also shown.

Indexing (details)


Subject
Organic chemistry
Classification
0490: Organic chemistry
Identifier / keyword
Pure sciences, Aryl acetylenes, Copper(I), Cross-coupling, Vinyl iodides
Title
Copper(I)-catalyzed cross -coupling reactions and their applications
Author
Saejueng, Pranorm
Number of pages
161
Publication year
2007
Degree date
2007
School code
0118
Source
DAI-B 68/02, Dissertation Abstracts International
Place of publication
Ann Arbor
Country of publication
United States
Advisor
Venkataraman, Dhandapani
University/institution
University of Massachusetts Amherst
University location
United States -- Massachusetts
Degree
Ph.D.
Source type
Dissertations & Theses
Language
English
Document type
Dissertation/Thesis
Dissertation/thesis number
3254915
ProQuest document ID
304845350
Copyright
Database copyright ProQuest LLC; ProQuest does not claim copyright in the individual underlying works.
Document URL
http://search.proquest.com/docview/304845350
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