Aryne cycloaddition reactions of benzodioxasilines as aryne precursors generated by catalytic reductive ortho-C H silylation of phenols with traceless acetal directing groups
| Autor: | Junha Jeon, Parham Asgari, Udaya Sree Dakarapu, Hiep H. Nguyen |
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| Rok vydání: | 2017 |
| Předmět: |
Steric effects
Silylation 010405 organic chemistry Chemistry Trifluoromethanesulfonic anhydride Organic Chemistry Acetal 010402 general chemistry 01 natural sciences Biochemistry Aryne Article Cycloaddition 0104 chemical sciences Catalysis chemistry.chemical_compound Drug Discovery Organic chemistry Phenols |
| Zdroj: | Tetrahedron. 73:4052-4061 |
| ISSN: | 0040-4020 |
| DOI: | 10.1016/j.tet.2016.12.002 |
| Popis: | Diversely substituted arylsilyl triflates, as aryne precursors for aryne cycloaddition reactions, were accessed from benzodioxasilines. Catalytic reductive C H ortho- silylation of phenols with traceless acetal directing groups was exploited to prepare benzodioxasilines. Sequential addition of MeLi and then trifluoromethanesulfonic anhydride to benzodioxasilines provided arylsilyl triflates in a single pot. Notably, this approach was successfully utilized to prepare sterically hindered 1,2,3-trisubstituted arylsilyl triflates, which ultimately underwent fluoride-mediated aryne cycloaddition. |
| Databáze: | OpenAIRE |
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