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Issue 10, 2015
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Rh-catalyzed reagent-free ring expansion of cyclobutenones and benzocyclobutenones

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Abstract

Here we report a reagent-free rhodium-catalyzed ring-expansion reaction via C–C cleavage of cyclobutenones. A variety of poly-substituted cyclopentenones and 1-indanones can be synthesized from simple cyclobutenones and benzocyclobutenones. The reaction condition is near pH neutral without additional oxidants or reductants. The potential for developing a dynamic kinetic asymmetric transformation of this reaction has also been demonstrated. Further study supports the proposed pathway involving Rh-insertion into the cyclobutenone C–C bond, followed by β-hydrogen elimination, olefin insertion and reductive elimination.

Graphical abstract: Rh-catalyzed reagent-free ring expansion of cyclobutenones and benzocyclobutenones

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Publication details

The article was received on 25 May 2015, accepted on 09 Jul 2015 and first published on 10 Jul 2015


Article type: Edge Article
DOI: 10.1039/C5SC01875G
Citation: Chem. Sci., 2015,6, 5440-5445
  • Open access: Creative Commons BY-NC license
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    Rh-catalyzed reagent-free ring expansion of cyclobutenones and benzocyclobutenones

    P. Chen, J. Sieber, C. H. Senanayake and G. Dong, Chem. Sci., 2015, 6, 5440
    DOI: 10.1039/C5SC01875G

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