Transition Metal Catalyst‐Free, Base‐Promoted 1,2‐Additions of Polyfluorophenylboronates to Aldehydes and Ketones
| Autor: | Todd B. Marder, Xiaoling Luo, Udo Radius, Goutam Kumar Kole, Alexandra Friedrich, Zhiqiang Liu, Yudha P. Budiman, Ya-Ming Tian, Stephen A. Westcott |
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| Rok vydání: | 2021 |
| Předmět: |
Base (chemistry)
chemistry.chemical_element Alcohol 010402 general chemistry 01 natural sciences Catalysis chemistry.chemical_compound Transition metal 1 2‐Additions fluoroarene Organic chemistry Research Articles chemistry.chemical_classification 010405 organic chemistry Hydrogen bond Chemistry alcohol Free base General Chemistry General Medicine 0104 chemical sciences transition metal-free 1 2-addition reaction Fluorine Counterion ddc:546 Research Article boronate esters |
| Zdroj: | Angewandte Chemie (International Ed. in English) |
| ISSN: | 1521-3757 0044-8249 |
| Popis: | A novel protocol for the transition metal‐free 1,2‐addition of polyfluoroaryl boronate esters to aldehydes and ketones is reported, which provides secondary alcohols, tertiary alcohols, and ketones. Control experiments and DFT calculations indicate that both the ortho‐F substituents on the polyfluorophenyl boronates and the counterion K+ in the carbonate base are critical. The distinguishing features of this procedure include the employment of commercially available starting materials and the broad scope of the reaction with a wide variety of carbonyl compounds giving moderate to excellent yields. Intriguing structural features involving O−H⋅⋅⋅O and O−H⋅⋅⋅N hydrogen bonding, as well as arene‐perfluoroarene interactions, in this series of racemic polyfluoroaryl carbinols have also been addressed. Herein we report a transition metal‐free procedure for the base‐promoted 1,2‐addition of polyfluorophenylboronates to aldehydes and ketones to generate organofluorine‐containing alcohols in yields up to 93 %. |
| Databáze: | OpenAIRE |
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