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Selective Pd-catalyzed oxidative coupling of anilides with olefins through C-H bond activation at room temperature.
| Content Provider | Semantic Scholar |
|---|---|
| Author | Boele, Maarten D. K. Strijdonck, Gino P. F. Van Vries, André H. M. De Kamer, Paul C. J. Vries, Johannes G. De Leeuwen, Piet W. N. M. Van |
| Copyright Year | 2002 |
| Abstract | Using a high-throughput experimentation approach we found a selective and mild Pd-catalyzed oxidative coupling reaction between anilide derivatives and acrylates that occurs through ortho C-H bond activation. The reaction is carried out in an acidic environment and occurs even at room temperature with use of a cheap oxidant (benzoquinone) in yields up to 91%. The benzoquinone possibly also functions as a ligand, stabilizing the catalyst. From the electronic dependence of the reaction and the observed kinetic isotope effect (kH/kD = 3) the key step of the catalytic cycle is believed to be electrophilic attack by a [PdOAc]+ complex on the pi-system of the arene. |
| File Format | PDF HTM / HTML |
| DOI | 10.1021/ja0176907 |
| PubMed reference number | 11853427 |
| Journal | Medline |
| Volume Number | 124 |
| Issue Number | 8 |
| Alternate Webpage(s) | https://www.rug.nl/research/portal/files/14467465/2002JAmChemSocBoeleSupp.pdf |
| Alternate Webpage(s) | http://www.rug.nl/research/portal/files/14467466/2002JAmChemSocBoele.pdf |
| Alternate Webpage(s) | https://www.rug.nl/research/portal/files/14467466/2002JAmChemSocBoele.pdf |
| Alternate Webpage(s) | https://doi.org/10.1021/ja0176907 |
| Journal | Journal of the American Chemical Society |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
