Formation of Seven-Membered Rings by Ring-Closing Metathesis of Vinyl Bromides
| Autor: | Richard C. D. Brown, Vachiraporn Ajavakom, Potchanee Pandokrak, Sofia S. Salim, Gamal A. I. Moustafa, Richard K. Bellingham, Joseph T. Hill-Cousins, Anawat Ajavakom |
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| Rok vydání: | 2022 |
| Předmět: | |
| Zdroj: | Synlett. 33:1453-1457 |
| ISSN: | 1437-2096 0936-5214 |
| DOI: | 10.1055/a-1845-4195 |
| Popis: | A Grubbs II catalyst mediated ring-closing metathesis (RCM) of monobrominated dienes is reported to proceed in moderate to good yields (40–80%) where the linking chain contains five atoms, leading to carbocyclic and heterocyclic seven-membered bromoolefins. Notably, RCM to form five-, six-, or eight-membered bromoolefins was unsuccessful, with the exception of one example where RCM afforded diethyl 3-bromocyclohex-3-ene-1,1-dicarboxylate. In this case, a bromomethyl-substituted cyclohexene was obtained as a byproduct. The utility of selected bromoolefin RCM products was demonstrated through their participation in Suzuki–Miyaura reactions. Vinylic halide exchange (Br → Cl) was noted as a side reaction under RCM conditions. |
| Databáze: | OpenAIRE |
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