Copper-Catalyzed Asymmetric Radical 1,2-Carboalkynylation of Alkenes with Alkyl Halides and Terminal Alkynes
| Autor: | Yu-Feng Zhang, Qiang-Shuai Gu, Liu Ye, Tian-Ya Zhan, Xin-Yuan Liu, Ning-Yuan Yang, Xiao-Yang Dong, Fu-Li Wang, Jiang-Tao Cheng, Ji-Jun Chen, Zhong-Liang Li |
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| Rok vydání: | 2020 |
| Předmět: |
chemistry.chemical_classification
Denticity Silylation biology Aryl Side reaction Cinchona chemistry.chemical_element General Chemistry 010402 general chemistry biology.organism_classification 01 natural sciences Biochemistry Combinatorial chemistry Copper Catalysis 0104 chemical sciences chemistry.chemical_compound Colloid and Surface Chemistry chemistry Glaser coupling Alkyl |
| Zdroj: | Journal of the American Chemical Society. 142(20) |
| ISSN: | 1520-5126 |
| Popis: | A copper-catalyzed intermolecular three-component asymmetric radical 1,2-carboalkynylation of alkenes has been developed, providing straightforward access to diverse chiral alkynes from readily available alkyl halides and terminal alkynes. The utilization of a cinchona alkaloid-derived multidentate N,N,P-ligand is crucial for the efficient radical generation from mildly oxidative precursors by copper and the effective inhibition of the undesired Glaser coupling side reaction. The substrate scope is broad, covering (hetero)aryl-, alkynyl-, and aminocarbonyl-substituted alkenes, (hetero)aryl and alkyl as well as silyl alkynes, and tertiary to primary alkyl radical precursors with excellent functional group compatibility. Facile transformations of the obtained chiral alkynes have also been demonstrated, highlighting the excellent complementarity of this protocol to direct 1,2-dicarbofunctionalization reactions with C(sp2/sp3)-based reagents. |
| Databáze: | OpenAIRE |
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