Synthesis of Functionalized 9-Substituted Fluorene Derivatives via Boron Trifluoride Catalysed Reaction of Coplanar 9-(Phenylethynyl)-9H-fluoren-9-ols, Aryl Aminoamides and N-Bromosuccinimide
A boron trifluoride catalysed reaction of coplanar 9-(phenylethynyl)-9H-fluoren-9-ols with various 2-aminobenzamides affords a number of highly functionalized, conjugated (Z)-2-((2-(9H-fluoren-9-ylidene)-1-phenylethylidene)amino) benzamides in excellent yield. The reaction in the presence of N-brom...
| Main Authors: | , |
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| Format: | Article |
| Language: | English |
| Published: |
Georg Thieme Verlag KG
2021-01-01
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| Series: | SynOpen |
| Subjects: | |
| Online Access: | http://www.thieme-connect.de/DOI/DOI?10.1055/s-0040-1706015 |
| Summary: | A boron trifluoride catalysed reaction of coplanar 9-(phenylethynyl)-9H-fluoren-9-ols with various 2-aminobenzamides affords a number of highly functionalized, conjugated (Z)-2-((2-(9H-fluoren-9-ylidene)-1-phenylethylidene)amino) benzamides in excellent yield. The reaction in the presence of N-bromosuccinimide affords (E)-5-bromo-2-((2-bromo-2-(9H-fluoren-9-ylidene)-1-phenylethylidene)amino)benzamides in very good yields. The scope of the reaction is demonstrated by selecting N-aryl substituted 2-aminobenzamides and aminosulfonamides as reaction partners. The structures of representative compounds were established by single-crystal XRD analysis. Based on the structure of the products, a plausible mechanism via formation of allene carbocation intermediates is proposed. |
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| ISSN: | 2509-9396 |