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Catalyst-free [2 + 2] photocycloadditions between benzils and olefins under visible light.
Tinelli, Roberto; Ravelli, Davide; Basso, Andrea; Tarantino, Serena C; Capaldo, Luca.
Afiliación
  • Tinelli R; PhotoGreen Lab, Department of Chemistry, University of Pavia, Viale Taramelli 12, 27100, Pavia, Italy.
  • Ravelli D; Institute of Organic Chemistry, University of Vienna, 1090, Vienna, Austria.
  • Basso A; PhotoGreen Lab, Department of Chemistry, University of Pavia, Viale Taramelli 12, 27100, Pavia, Italy.
  • Tarantino SC; Department of Chemistry and Industrial Chemistry, University of Genova, Via Dodecaneso 31, 16146, Genoa, Italy.
  • Capaldo L; Department of Chemistry, University of Pavia, Viale Taramelli 12, 27100, Pavia, Italy.
Photochem Photobiol Sci ; 21(5): 695-703, 2022 May.
Article en En | MEDLINE | ID: mdl-34792791
The catalyst-free [2 + 2] photocycloaddition between benzils and simple olefins is reported. The adoption of visible light proved essential for the transformation, as shorter wavelengths led to uncontrolled decomposition. When cyclic olefins were used, the reaction occurred smoothly to afford the expected oxetanes regio- and stereoselectively after 24 h of irradiation. In contrast, in the case of acyclic olefins, longer reaction times were typically required and small amounts (ca. 20%) of [4 + 2] photocycloadducts and by-products deriving from competitive hydrogen atom abstraction were observed. The selectivity of the transformation could be consistently improved by decreasing the reaction temperature, thus restoring the desired [2 + 2] reactivity. An overall mechanistic picture is also offered based on the chemical and photophysical quenching experiments and the stereochemical output is rationalized based on Griesbeck models.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Alquenos / Luz Idioma: En Revista: Photochem Photobiol Sci Asunto de la revista: BIOLOGIA / QUIMICA Año: 2022 Tipo del documento: Article País de afiliación: Italia Pais de publicación: Reino Unido
Texto completo
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Alquenos / Luz Idioma: En Revista: Photochem Photobiol Sci Asunto de la revista: BIOLOGIA / QUIMICA Año: 2022 Tipo del documento: Article País de afiliación: Italia Pais de publicación: Reino Unido