We describe the synthesis of seven C2-alkylcarbazoles via a sequence of Buchwald–Hartwig coupling of arylamines with aryl halides followed by oxidative cyclization of the resulting diarylamines. Methyl groups at the positions 4 and 5 were introduced by taking advantage of the ortho-directed palladation of meta-pivaloyloxy-substituted diarylamines and subsequent conversion of the pivaloyloxy to methyl groups through Stille coupling of intermediate triflates. The obtained ethyl- and dimethylcarbazoles served as analytical standards for their identification in petroleum samples and source rocks.
| Identifer | oai:union.ndltd.org:DRESDEN/oai:qucosa:de:qucosa:90326 |
| Date | 18 April 2024 |
| Creators | Theumer, Gabriele, Bauer, Ingmar, Jäger, Anne, Schwark, Lorenz, Knölker, Hans-Joachim |
| Publisher | Wiley-VCH |
| Source Sets | Hochschulschriftenserver (HSSS) der SLUB Dresden |
| Language | English |
| Detected Language | English |
| Type | info:eu-repo/semantics/publishedVersion, doc-type:article, info:eu-repo/semantics/article, doc-type:Text |
| Rights | info:eu-repo/semantics/openAccess |
| Relation | 1099-0690, e202104292, 10.1002/ejoc.202200456 |
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