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

文献情報

出版日 2019-10-12

DOI 10.1039/C9QO01028A

インパクトファクター 5.281

著者

Arto Valkonen, Carlos A. M. Afonso, Nuno R. Candeias

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要旨

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.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

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

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