Rhodium(I)-catalyzed decarbonylative spirocyclization through C-C bond cleavage of benzocyclobutenones: an efficient approach to functionalized spirocycles.
| Autor: | Xu T; Department of Chemistry, University of Texas at Austin, 100 east 24th street, Austin, TX 78712 (USA) http://gbdong.cm.utexas.edu/, Savage NA, Dong G |
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| Jazyk: | angličtina |
| Zdroj: | Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2014 Feb 10; Vol. 53 (7), pp. 1891-5. Date of Electronic Publication: 2014 Jan 20. |
| DOI: | 10.1002/anie.201310149 |
| Abstrakt: | The rhodium-catalyzed formation of all-carbon spirocenters involves a decarbonylative coupling of trisubstituted cyclic olefins and benzocyclobutenones through CC activation. The metal-ligand combination [{Rh(CO)2 Cl}2 ]/P(C6 F5 )3 catalyzed this transformation most efficiently. A range of diverse spirocycles were synthesized in good to excellent yields and many sensitive functional groups were tolerated. A mechanistic study supports a hydrogen-transfer process that occurs through a β-H elimination/decarbonylation pathway. (Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.) |
| Databáze: | MEDLINE |
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