A base-catalyzed approach for the anti-Markovnikov hydration of styrene derivatives.
| Autor: | Pajk SP; Department of Chemistry, Colorado State University Fort Collins Colorado 80523 USA jeff.bandar@colostate.edu., Qi Z; Department of Chemistry, Colorado State University Fort Collins Colorado 80523 USA jeff.bandar@colostate.edu., Sujansky SJ; Department of Chemistry, Colorado State University Fort Collins Colorado 80523 USA jeff.bandar@colostate.edu., Bandar JS; Department of Chemistry, Colorado State University Fort Collins Colorado 80523 USA jeff.bandar@colostate.edu. |
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| Jazyk: | angličtina |
| Zdroj: | Chemical science [Chem Sci] 2022 Aug 26; Vol. 13 (38), pp. 11427-11432. Date of Electronic Publication: 2022 Aug 26 (Print Publication: 2022). |
| DOI: | 10.1039/d2sc02827a |
| Abstrakt: | The base-catalyzed addition of 1-cyclopropylethanol to styrene derivatives with an acidic reaction workup enables anti-Markovnikov hydration. The use of either catalytic organic superbase or crown ether-ligated inorganic base permits hydration of a wide variety of styrene derivatives, including electron-deficient, ortho -substituted and heteroaryl variants. This protocol complements alternative routes to terminal alcohols that rely on stoichiometric reduction and oxidation processes. The utility of this method is demonstrated through multigram scale reactions and its use in a two-step hydration/cyclization process of ortho -halogenated styrenes to prepare 2,3-dihydrobenzofuran derivatives. Competing Interests: There are no conflicts to declare. (This journal is © The Royal Society of Chemistry.) |
| Databáze: | MEDLINE |
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