Issue 22, 2019

Synthesis of silacyclopent-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.

Graphical abstract: Synthesis of silacyclopent-2-en-4-ols via intramolecular [2 + 2] photocycloaddition of benzoyl(allyl)silanes

Supplementary files

Article information

Article type
Research Article
Submitted
21 Aug 2019
Accepted
10 Oct 2019
First published
12 Oct 2019
This article is Open Access
Creative Commons BY-NC license

Org. Chem. Front., 2019,6, 3793-3798

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

J. R. Vale, A. Valkonen, C. A. M. Afonso and N. R. Candeias, Org. Chem. Front., 2019, 6, 3793 DOI: 10.1039/C9QO01028A

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