Interruption of Formal Schmidt Rearrangement/Hosomi–Sakurai Reaction of Vinyl Azides with Allyl/Propargylsilanes
| Autor: | Ling Pan, Haiyan Yuan, Zhenhua Liu, Jingping Zhang, Shanshan Cao, Guichun Fang |
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| Rok vydání: | 2018 |
| Předmět: |
Reaction conditions
Nucleophilic addition 010405 organic chemistry Chemistry organic chemicals Organic Chemistry Bond formation Carbocation 010402 general chemistry 01 natural sciences Biochemistry Medicinal chemistry 0104 chemical sciences Fragmentation (mass spectrometry) Lewis acids and bases Physical and Theoretical Chemistry Sakurai reaction |
| Zdroj: | Organic Letters. 20:7113-7116 |
| ISSN: | 1523-7052 1523-7060 |
| Popis: | An interrupted Schmidt rearrangement/Hosomi–Sakurai reaction of N-tosyl and S-substituted vinyl azides is reported. With BF3·Et2O as a Lewis acid promoter, the denitrogenative fragmentation of vinyl azides facilitates the generation of the N/S-stabilized carbocations, which further undergo nucleophilic addition by allyl/propargylsilanes for C–C bond formation. As a result, a variety of homoallylic/allenylic amines can be afforded in good yields under mild reaction conditions with well-defined functional-group tolerance. |
| Databáze: | OpenAIRE |
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