Access to Functionalized E-Allylsilanes and E-Alkenylsilanes through Visible-Light-Driven Radical Hydrosilylation of Mono- and Disubstituted Allenes
| Autor: | Shaozhong Wang, Yong Liang, Wenxuan Zhao, Yanyao Cai, Zhu-Jun Yao |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
chemistry.chemical_classification
010405 organic chemistry Hydrosilylation Allene Organic Chemistry 010402 general chemistry 01 natural sciences Biochemistry Medicinal chemistry 0104 chemical sciences Adduct chemistry.chemical_compound chemistry Photocatalysis Thiol Stereoselectivity Physical and Theoretical Chemistry Eosin Y Visible spectrum |
| Zdroj: | Organic Letters. 21:9836-9840 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/acs.orglett.9b03679 |
| Popis: | A visible-light-driven radical hydrosilylation of allene has been achieved by using eosin Y as the photocatalyst, with thiol and base as additives. Depending on allenes, two types of adducts with E-selectivity were obtained. It was demonstrated that monosubstituted nonarylated allenes reacted to give linear E-allylsilanes, while 1,3-disubstituted electron-deficient allenes afforded E-alkenylsilanes. A radical mechanism was proposed to account for the chemo-, regio-, and stereoselective formation of these functionalized silicon-containing compounds. |
| Databáze: | OpenAIRE |
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