A1 Journal article (refereed)
Synthesis of silacyclopent-2-en-4-ols via intramolecular [2 + 2] photocycloaddition of benzoyl(allyl)silanes (2019)


Vale, Joao R.; Valkonen, Arto; Afonso, Carlos A. M.; Candeias, Nuno R. (2019). Synthesis of silacyclopent-2-en-4-ols via intramolecular [2 + 2] photocycloaddition of benzoyl(allyl)silanes. Organic Chemistry Frontiers, 6 (22), 3793-3798. DOI: 10.1039/C9QO01028A


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Publication details

All authors or editors: Vale, Joao R.; Valkonen, Arto; Afonso, Carlos A. M.; Candeias, Nuno R.

Journal or series: Organic Chemistry Frontiers

ISSN: 2052-4110

eISSN: 2052-4129

Publication year: 2019

Volume: 6

Issue number: 22

Pages range: 3793-3798

Publisher: Royal Society of Chemistry

Publication country: United Kingdom

Publication language: English

DOI: https://doi.org/10.1039/C9QO01028A

Open Access: Open access publication published in a hybrid channel

Publication is parallel published (JYX): https://jyx.jyu.fi/handle/123456789/66524


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.


Keywords: organometallic compounds; silicon; chemical synthesis


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Ministry reporting: Yes

Reporting Year: 2019

JUFO rating: 1


Last updated on 2020-18-08 at 13:28