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Intermolecular 2 + 2 Carbonyl-Olefin Photocycloadditions Enabled by Cu(I)-Norbornene MLCT.

  • Author(s): Flores, Daniel M;
  • Schmidt, Valerie A
  • et al.
Abstract

Photocycloadditions are often typified by the oxetane-forming Paternò-Büchi reaction. However, the mechanistic constraints of carbonyl excitation and olefin interception have limited this attractive oxetane-forming pathway. Here we describe the use of a Cu(I) precatalyst that achieves selective olefin activation via coordination to the metal center. Significantly, this intermolecular 2 + 2 carbonyl-olefin photocycloaddition engages alkyl ketones, which are more challenging to accommodate via direct irradiation pathways. Mechanistic investigations support the in situ formation of a Cu-norbornene resting state that undergoes a MLCT leading to oxetane formation.

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