Metal‐Free C−H Borylation of N‐Heteroarenes by Boron Trifluoride
| Autor: | Timo Repo, Konstantin Chernichenko, Karina Moslova, Imre Pápai, Martin Nieger, Dénes Berta, Vladimir Iashin |
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| Přispěvatelé: | Department of Chemistry |
| Rok vydání: | 2020 |
| Předmět: |
MECHANISM
Steric effects 116 Chemical sciences SALTS 010402 general chemistry 01 natural sciences Borylation C−H activation Catalysis Frustrated Lewis pair Coupling reaction boron trifluoride chemistry.chemical_compound borylation BOND ACTIVATION C-H activation Boron trifluoride Tetramethylammonium Full Paper 010405 organic chemistry Organic Chemistry ARENE General Chemistry Full Papers FRUSTRATED-LEWIS-PAIR Combinatorial chemistry REACTIVITY 0104 chemical sciences 3. Good health C−H activation | Hot Paper chemistry Main group element COMPLEXES protodeboronation frustrated Lewis pairs GENERATION |
| Zdroj: | Chemistry (Weinheim an Der Bergstrasse, Germany) |
| ISSN: | 1521-3765 0947-6539 |
| Popis: | Organoboron compounds are essential reagents in modern C−C coupling reactions. Their synthesis via catalytic C−H borylation by main group elements is emerging as a powerful tool alternative to transition metal based catalysis. Herein, a straightforward metal‐free synthesis of aryldifluoroboranes from BF3 and heteroarenes is reported. The reaction is assisted by sterically hindered amines and catalytic amounts of thioureas. According to computational studies the reaction proceeds via frustrated Lewis pair (FLP) mechanism. The obtained aryldifluoroboranes are further stabilized against destructive protodeborylation by converting them to the corresponding air stable tetramethylammonium organotrifluoroborates. C−H activation: Indoles, pyrroles and indolenines undergo C−H borylation by boron trifluoride with assistance of base and thiourea additives. |
| Databáze: | OpenAIRE |
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