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Synthesis of silacylopent-2-en-4-ols via intramolecular [2+2] photocycloaddition of benzoyl(allyl)silanes

Abstract

Organosilicon compounds are versatile units with a wide range of uses from medicinal chemistry to the field of organic electronics. An unprecedented method for the synthesis of novel diaryl-substituted silacyclopentenols via blue-light promoted intramolecular [2+2] photocycloaddition of acyl silanes is herein disclosed. Additionally, the present findings demonstrate the influence of the olefin substituents in controlling the regioselectivity of the intramolecular Paternò-Büchi reaction, providing silacycles different from previously reported ones. The high degree of functionalization of these compounds makes them attractive precursors to other synthetically challenging silacyclopentanes.

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Publication details

The article was received on 21 Aug 2019, accepted on 10 Oct 2019 and first published on 12 Oct 2019


Article type: Research Article
DOI: 10.1039/C9QO01028A
Org. Chem. Front., 2019, Accepted Manuscript
  • Open access: Creative Commons BY-NC license
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    Synthesis of silacylopent-2-en-4-ols via intramolecular [2+2] photocycloaddition of benzoyl(allyl)silanes

    J. Rafael Vale, A. Valkonen, C. A. M. Afonso and N. R. Candeias, Org. Chem. Front., 2019, Accepted Manuscript , DOI: 10.1039/C9QO01028A

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