Short syntheses of 1-substituted dibenzothiophene derivatives.
| Autor: | Welsh EN; Department of Chemistry, Dalhousie University, Halifax, Nova Scotia, Canada B3H 4R2. aspeed@dal.ca., Robertson KN; Department of Chemistry, Saint Mary's University, Halifax, Nova Scotia, Canada B3H 3C3., Speed AWH; Department of Chemistry, Dalhousie University, Halifax, Nova Scotia, Canada B3H 4R2. aspeed@dal.ca. |
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| Jazyk: | angličtina |
| Zdroj: | Organic & biomolecular chemistry [Org Biomol Chem] 2021 Mar 11; Vol. 19 (9), pp. 2000-2007. |
| DOI: | 10.1039/d0ob01839b |
| Abstrakt: | The 1-substituted dibenzothiophene motif is an unusual substitution pattern that has previously been accessed via a multi-step synthesis. We demonstrate a simple one-pot preparation of 1-lithiodibenzothiophene from commercial materials via a cascade of two benzyne additions and conversion to several derivatives by addition of electrophiles. A chiral amine containing the 1-dibenzothiophene motif was also prepared. This work avoids the use of precious metals or tert-butyllithium and is much shorter and more convenient than existing routes to 1-substituted dibenzothiophenes. |
| Databáze: | MEDLINE |
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