4.8 Article

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

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CHEMICAL SCIENCE
卷 6, 期 10, 页码 5440-5445

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ROYAL SOC CHEMISTRY
DOI: 10.1039/c5sc01875g

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  1. CPRIT [R 1118]
  2. NIGMS [R01GM109054-01]
  3. Welch Foundation [F 1781]

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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 beta-hydrogen elimination, olefin insertion and reductive elimination.

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