Abstract/Details

Copper-catalyzed cross -coupling reactions: The formation of carbon-carbon and carbon -sulfur bonds


2005 2005

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Abstract (summary)

We have developed copper-catalyzed cross-coupling reactions for the formation of carbon-carbon and carbon-sulfur bonds. These newly developed methods demonstrate that the conditions of the traditional Ullmann reaction can be improved. We describe the synthesis of diarylacetylenes through the cross-coupling of aryl iodides and phenylacetylene using [Cu(phen)PPh 3Br] as the catalyst. This method is then utilized for the synthesis of 2-aryl-benzo[b]furans via a copper-catalyzed cross-coupling reaction between aryl acetylenes and 2-iodophenols and a subsequent 5-endo-dig cyclization. The formation of carbon-acetylene bonds is also extended to include vinyl iodides for the purpose of synthesizing 1,3-enynes. Due the lack of a general metal-mediated synthesis of aryl sulfides, we developed a copper-catalyzed cross-coupling reaction between aryl iodides and thiols using a catalytic amount of CuI and 2,9-dimethyl-1,10-phenanthroline as an additive. This method was also extended to include vinyl iodides for the synthesis of vinyl sulfides using [Cu(phen)(PPh3)2]NO3 as the catalyst. All of these methods afford the desired product in good to excellent yields without the use of palladium or expensive/air sensitive additives.

Indexing (details)


Subject
Organic chemistry
Classification
0490: Organic chemistry
Identifier / keyword
Pure sciences; Carbon-carbon bond; Carbon-sulfur bonds; Copper; Cross-coupling
Title
Copper-catalyzed cross -coupling reactions: The formation of carbon-carbon and carbon -sulfur bonds
Author
Bates, Craig G.
Number of pages
146
Publication year
2005
Degree date
2005
School code
0118
Source
DAI-B 66/06, Dissertation Abstracts International
Place of publication
Ann Arbor
Country of publication
United States
ISBN
0542197421, 9780542197420
Advisor
Venkataraman, D.
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
3179856
ProQuest document ID
304994006
Copyright
Database copyright ProQuest LLC; ProQuest does not claim copyright in the individual underlying works.
Document URL
http://search.proquest.com/docview/304994006
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