Iron-Catalyzed Contrasteric Functionalization of Allenic C(sp(2))–H Bonds: Synthesis of α-Aminoalkyl 1,1-Disubstituted Allenes
| Autor: | Austin C. Durham, Yi-Ming Wang, Philip N. Palermo, Sarah G. Scrivener, Ruihan Wang, Yidong Wang, Ethan Murphy, Xiao-Dong Zuo |
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| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: |
Steric effects
Models Molecular Molecular Structure Chemistry Iron Cationic polymerization Iminium Ether Hydrogen Bonding General Chemistry Biochemistry Combinatorial chemistry Article Catalysis Hydrocarbons Alkadienes chemistry.chemical_compound Colloid and Surface Chemistry Reagent Electrophile Hemiaminal |
| Zdroj: | J Am Chem Soc |
| Popis: | An iron-catalyzed C-H functionalization of simple monosubstituted allenes is reported. An efficient protocol for this process was made possible by the use of a newly developed electron-rich and sterically hindered cationic cyclopentadienyliron dicarbonyl complex as the catalyst and N-sulfonyl hemiaminal ether reagents as precursors to iminium ion electrophiles. Under optimized conditions, the use of a mild, functional-group-tolerant base enabled the conversion of a range of monoalkyl allenes to their allenylic sulfonamido 1,1-disubstituted derivatives, a previously unreported and contrasteric regiochemical outcome for the C-H functionalization of electronically unbiased and directing-group-free allenes. |
| Databáze: | OpenAIRE |
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