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

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 silan...

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Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2019-11, Vol.6 (22), p.3793-3798
Main Authors: Vale, João R, Valkonen, Arto, Afonso, Carlos A M, Candeias, Nuno R
Format: Article
Language:English
Subjects:
Computer applications
Crystallography
NMR
Nuclear magnetic resonance
Organic chemistry
Organosilicon compounds
Regioselectivity
Silanes
Synthesis
X-ray diffraction
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Summary: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.
ISSN:2052-4110
2052-4110
DOI:10.1039/c9qo01028a