Jump to main content
Jump to site search

Issue 10, 2015
Previous Article Next Article

Rh-catalyzed reagent-free ring expansion of cyclobutenones and benzocyclobutenones

Author affiliations

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

Back to tab navigation
Please wait while Download options loads

Supplementary files

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
  •   Request permissions

    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

Search articles by author