: Dearomative cycloadditions are a powerful tool to access a large chemical space exploiting simple and ubiquitous building blocks. The energetic burden due to the loss of aromaticity has however greatly limited their synthetic potential. We devised a general intramolecular method that overcomes these limitations thanks to the photosensitization of allenamides. The visible-light-promoted process gives complex [2.2.2]-(hetero)-bicyclooctadienes at room temperature, likely through the stabilization of transient (bi)radicals by naphthalene. The reaction tolerates several valuable functionalities, offering a convenient handle for a myriad of applications, including original isoindoles and metal complexes.

Visible-Light Promoted Intramolecular para-Cycloadditions on Simple Aromatics / Chiminelli, Maurizio; Serafino, Andrea; Ruggeri, Davide; Marchio, Luciano; Bigi, Franca; Maggi, Raimondo; Malacria, Max; Maestri, Giovanni. - In: ANGEWANDTE CHEMIE. - ISSN 1521-3773. - 62:12(2023), p. e202216817.202216817. [10.1002/anie.202216817]

Visible-Light Promoted Intramolecular para-Cycloadditions on Simple Aromatics

Chiminelli, Maurizio;Serafino, Andrea;Ruggeri, Davide;Marchio, Luciano;Bigi, Franca;Maggi, Raimondo;Maestri, Giovanni
2023-01-01

Abstract

: Dearomative cycloadditions are a powerful tool to access a large chemical space exploiting simple and ubiquitous building blocks. The energetic burden due to the loss of aromaticity has however greatly limited their synthetic potential. We devised a general intramolecular method that overcomes these limitations thanks to the photosensitization of allenamides. The visible-light-promoted process gives complex [2.2.2]-(hetero)-bicyclooctadienes at room temperature, likely through the stabilization of transient (bi)radicals by naphthalene. The reaction tolerates several valuable functionalities, offering a convenient handle for a myriad of applications, including original isoindoles and metal complexes.
2023
Visible-Light Promoted Intramolecular para-Cycloadditions on Simple Aromatics / Chiminelli, Maurizio; Serafino, Andrea; Ruggeri, Davide; Marchio, Luciano; Bigi, Franca; Maggi, Raimondo; Malacria, Max; Maestri, Giovanni. - In: ANGEWANDTE CHEMIE. - ISSN 1521-3773. - 62:12(2023), p. e202216817.202216817. [10.1002/anie.202216817]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11381/2940391
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