Chemoselective Hydrosilylation of the α,β-Site Double Bond in α,β- and α,β,γ,δ-Unsaturated Ketones Catalyzed by Macrosteric Borane Promoted by Hexafluoro-2-propanol
| Autor: | Tang Lei, Hua Zhang, Yu Dong, Shuai He, Xiao-Yu Zhan, Ji-Yu Wang, Jian Yang, Zhi-Chuan Shi |
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| Rok vydání: | 2020 |
| Předmět: |
Reaction conditions
chemistry.chemical_classification Hydrogen Double bond 010405 organic chemistry Hydrosilylation Organic Chemistry chemistry.chemical_element Borane 010402 general chemistry 01 natural sciences Hexafluoro-2-propanol Medicinal chemistry 0104 chemical sciences Catalysis chemistry.chemical_compound chemistry |
| Zdroj: | The Journal of Organic Chemistry. 85:6578-6592 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/acs.joc.0c00568 |
| Popis: | The B(C6F5)3-catalyzed chemoselective hydrosilylation of α,β- and α,β,γ,δ-unsaturated ketones into the corresponding non-symmetric ketones in mild reaction conditions is developed. Nearly 55 substrates including those bearing reducible functional groups such as alkynyl, alkenyl, cyano, and aromatic heterocycles are chemoselectively hydrosilylated in good to excellent yields. Isotope-labeling studies revealed that hexafluoro-2-propanol also served as a hydrogen source in the process. |
| Databáze: | OpenAIRE |
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