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| Content Provider | World Health Organization (WHO)-Global Index Medicus |
|---|---|
| Author | Algarra, Andrés G. Khamker, Qudsia Singh, Kuldip Macgregor, Stuart A. Davies, David L. Mcmullin, Claire L. Villa-marcos, Barbara |
| Description | Author Affiliation: Algarra AG ( Institute of Chemical Sciences, Heriot-Watt University, Edinburgh EH14 4AS (UK).) |
| Abstract | Detailed experimental and computational studies have been carried out on the oxidative coupling of the alkenes $C_{2}H_{3}Y$ $(Y=CO_{2}Me$ (a), Ph (b), C(O)Me (c)) with 3-aryl-5-R-pyrazoles (R=Me (1 a), Ph (1 b), $CF_{3}$ (1 c)) using a $[Rh(MeCN)_{3}Cp*][PF_{6}]_{2}/Cu(OAc)_{2}⋅H_{2}O$ catalyst system. In the reaction of methyl acrylate with 1 a, up to five products (2 aa–6 aa) were formed, including the trans monovinyl product, either complexed within a novel $Cu^{I}$ dimer (2 aa) or as the free species (3 aa), and a divinyl species (6 aa); both 3 aa and 6 aa underwent cyclisation by an aza-Michael reaction to give fused heterocycles 4 aa and 5 aa, respectively. With styrene, only trans mono- and divinylation products were observed, whereas with methyl vinyl ketone, a stronger Michael acceptor, only cyclised oxidative coupling products were formed. Density functional theory calculations were performed to characterise the different migratory insertion and β-H transfer steps implicated in the reactions of 1 a with methyl acrylate and styrene. The calculations showed a clear kinetic preference for 2,1-insertion and the formation of trans vinyl products, consistent with the experimental results. |
| ISSN | 09476539 |
| e-ISSN | 15213765 |
| Journal | Chemistry - A European Journal |
| Issue Number | 7 |
| Volume Number | 21 |
| Language | English |
| Publisher | Wiley-VCH;ChemPubSoc Europe |
| Publisher Date | 2015-02-09 |
| Publisher Place | Germany |
| Access Restriction | Open |
| Subject Keyword | Chemistry |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Catalysis |
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