Journal article
Stereospecific preparation of (1E,3E,5E)-3.4-difluoro-1,6-diphenylhexatriene and (2E,4E,6E)-diethyl-4,5-difluoroocta-2,4,6-trienedioate
Journal of fluorine chemistry, Vol.132(2), pp.128-130
02/01/2011
DOI: 10.1016/j.jfluchem.2010.12.008
Abstract
Palladium(0) catalyzed coupling of beta-bromostyrene (E/Z = 89/11) with (E)-(1,2-difluoro-1,2-ethenediyl)bis[tributylstannane], 1, in DMF at room temperature stereospecifically gave only (1E,3E,5E)-3,4-difluoro-1,6-diphenylhexatriene. Similarly, palladium(0) catalyzed coupling of (E)-ethyl 3-bromoacrylate as the vinyl halide precursor stereospecifically gave (2E,4E,6E)-diethyl-4,5-difluoroocta-2,4,6-trienedioate. This work demonstrates that a non-fluorine-containing vinyl bromide will selectively undergo coupling with 1 and enable the stereospecific preparation of a mixed polyene system. The (E)-ethyl 3-bromoacrylate coupling with 1 illustrates that mixed functionalized hexatriene systems can be easily accessed via this methodology. The X-ray structure of (2E,4E,6E)-diethyl-4,5-difluoroocta-2.4.6-trienedioate confirmed its structure. (C) 2010 Elsevier By. All rights reserved.
Details
- Title: Subtitle
- Stereospecific preparation of (1E,3E,5E)-3.4-difluoro-1,6-diphenylhexatriene and (2E,4E,6E)-diethyl-4,5-difluoroocta-2,4,6-trienedioate
- Creators
- Qibo Liu - Univ Iowa, Dept Chem, Iowa City, IA 52242 USADale C. Swenson - University of IowaDonald J. Burton - University of Iowa
- Resource Type
- Journal article
- Publication Details
- Journal of fluorine chemistry, Vol.132(2), pp.128-130
- Publisher
- Elsevier
- DOI
- 10.1016/j.jfluchem.2010.12.008
- ISSN
- 0022-1139
- eISSN
- 1873-3328
- Number of pages
- 3
- Grant note
- NSF; National Science Foundation (NSF)
- Language
- English
- Date published
- 02/01/2011
- Academic Unit
- Chemistry
- Record Identifier
- 9984622748002771
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