Synthesis and Reactions of 3,3-Difluoro-2-exo-methylidene Indolines
| Autor: | Mark Lautens, Nicolas Zeidan, Alexa Torelli, Bijan Mirabi, Matthew Zambri, Sven Unger, Christian Dank |
|---|---|
| Rok vydání: | 2020 |
| Předmět: |
Olefin fiber
Letter Recrystallization (geology) 010405 organic chemistry Aryl Organic Chemistry Electrophilic fluorination chemistry.chemical_element 010402 general chemistry 01 natural sciences 7. Clean energy Biochemistry Medicinal chemistry 0104 chemical sciences Rhodium chemistry.chemical_compound chemistry Nucleophile Electrophile Physical and Theoretical Chemistry Palladium |
| Zdroj: | Organic Letters |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/acs.orglett.0c01175 |
| Popis: | A dearomative electrophilic fluorination of 2-methylindoles is reported, delivering 3,3-difluoroindolines bearing an exomethylidene. The model substrate was synthesized on up to a 20 mmol scale and was purified by a practical recrystallization as a crystalline bench-stable, yet reactive solid. The olefin is amphoteric and can react both as a nucleophile and as an electrophile. A wide range of metal-free, palladium, rhodium, and copper reactions was explored, forming new C-H, C-B, C-C (alkyl and aryl), C-N, C-O, C-P, and C-S bonds. |
| Databáze: | OpenAIRE |
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