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Palladium-Catalyzed Access to Benzocyclobutenone-Derived Ketonitrones via C(sp2)-H Functionalization

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AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c01317

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  1. National Science Centre, Poland [UMO-2017/26/E/ST5/00388, UMO-2020/37/N/ST4/00777]
  2. Ministry of Science and Education, Poland [0235/DIA/2019/48]

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The palladium-catalyzed C(sp(2))-H functionalization of bromoaryl aldonitrones leading to benzocyclobutenone-derived ketonitrones is described. This method allows for the preparation of a wide range of strained, four-membered ketonitrones with broad functional group tolerance. Downstream transformations of the formed products were readily demonstrated, illustrating the synthetic utility of the obtained benzocyclobutenone-derived nitrones for the construction of polycyclic nitrogen-containing scaffolds.
The palladium-catalyzed C(sp(2))-H functionalization of bromoaryl aldonitrones leading to benzocyclobutenone-derived ketonitrones is described. This method allows for the preparation of a wide range of strained, four-membered ketonitrones with broad functional group tolerance. Downstream transformations of the formed products were readily demonstrated, illustrating the synthetic utility of the obtained benzocyclobutenone-derived nitrones for the construction of polycyclic nitrogen-containing scaffolds.

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