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Microwave synthesis and fluorous purification of 4-(tetrathienyl)butyric acid for self-assembled monolayer semiconductor applications
- Source :
-
Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry . Feb2008, Vol. 49 Issue 8, p1328-1330. 3p. - Publication Year :
- 2008
-
Abstract
- Abstract: Microwave-promoted synthesis and fluorous purification procedures have been employed successfully to generate 4-(tetrathienyl)butyric acid rapidly. Initially, a fluorous tag 1H,1H-perfluorooctylamine was tethered to 4-(thienyl)butyric acid via an amide traceless linkage. Subsequent, sequential α-bromination and Stille cross-coupling reactions with 2-(tributylstannyl)thiophene grew the fluorous-tagged 4-(oligothienyl)butyric acid efficiently. Each synthetic transformation was followed by a fluorous-solid phase extraction procedure to isolate the fluorous-tagged compound intermediate in excellent yield. Finally, the fluorous tag was cleaved by microwave-promoted saponification of the amide bond to liberate the desired 4-(tetrathienyl)butyric acid. [Copyright &y& Elsevier]
- Subjects :
- *BUTYRIC acid
*FATTY acids
*AMINOBUTYRIC acid
*DICHLOROISOBUTYRIC acid
Subjects
Details
- Language :
- English
- ISSN :
- 00404039
- Volume :
- 49
- Issue :
- 8
- Database :
- Academic Search Index
- Journal :
- Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 28752919
- Full Text :
- https://doi.org/10.1016/j.tetlet.2007.12.101