Rh-Catalyzed Reagent-Free Ring Expansion of Cyclobutenones and Benzocyclobutenones
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Date
2015-07
Authors
Chen, Peng-hao
Sieber, Joshua
Senanayake, Chris H.
Dong, Guangbin B.
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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 beta-hydrogen elimination, olefin insertion and reductive elimination.
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Chen, Peng-hao, Joshua Sieber, Chris H. Senanayake, and Guangbin Dong. "Rh-catalyzed reagent-free ring expansion of cyclobutenones and benzocyclobutenones." Chemical Science 6, no. 10 (Jul., 2015): 5440-5445.