Triflic-Acid-Catalyzed Tandem Allylic Substitution–Cyclization Reaction of Alcohols with Thiophenols—Facile Access to Polysubstituted Thiochromans
| Autor: | Yongxin Li, Sumod A. Pullarkat, Minh Duy Vu, Ce Qing Foo, Abdul Sadeer, Sam S Shand |
|---|---|
| Přispěvatelé: | School of Physical and Mathematical Sciences |
| Jazyk: | angličtina |
| Rok vydání: | 2018 |
| Předmět: |
Allylic rearrangement
Tandem 010405 organic chemistry Chemistry General Chemical Engineering Chemistry::Biochemistry [Science] General Chemistry 010402 general chemistry Thiophenols 01 natural sciences Combinatorial chemistry Article 0104 chemical sciences Catalysis chemistry.chemical_compound Thiochromans Two-dimensional nuclear magnetic resonance spectroscopy Triflic acid |
| Zdroj: | ACS Omega |
| ISSN: | 2470-1343 |
| Popis: | Hitherto inaccessible multisubstituted thiochroman derivatives were constructed via the one-pot reaction of thiophenols with allylic alcohols catalyzed by 0.2 equiv triflic acid under metal-free conditions. A variety of thiochroman derivatives can be obtained by this straightforward protocol that allows the introduction of up to four substituents at various locations on the thiochroman skeleton. Relative conformations of all isolated products were confirmed by NOESY NMR studies, and a stepwise mechanism, proceeding via an allylic substitution-intramolecular cyclization protocol, is proposed on the basis of NMR experiments. Published version |
| Databáze: | OpenAIRE |
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