期刊
CCS CHEMISTRY
卷 1, 期 4, 页码 352-364出版社
CHINESE CHEMICAL SOC
DOI: 10.31635/ccschem.019.20190018
关键词
photoredox catalysis; alkene aminoarylation; alkene thioamination; amidyl radical; proton-coupled electron transfer; benzoindolizidinone; tylophorine
资金
- National 973 grant from the Ministry of Science and Technology [2011CB965300]
- National Natural Science Foundation of China [21232001, 21302106]
- National Science and Technology Major Project [2018ZX09711001]
- Tsinghua University Initiative Scientific Research Program
Photoredox-catalyzed aminoarylation and thioamination of unactivated alkenes have been developed, providing novel synthetic routes to access synthetically challenging quaternary carbon-centered benzoindolizidinones and trifluoromethylthiolated piperidines using readily available starting materials. Notably, these transformations were enabled by merging amidyl radical generation from N-alkyl benzamides with oxidant incorporation. Density functional theory calculations were performed to understand the reaction mechanism and to rationalize the regioselectivities. Moreover, the newly developed catalytic aminoarylation provided a convenient synthetic route for natural product tylophorine and its gem-dimethyl analogues with greatly improved drug-like properties such as enhanced solubility and stability. [GRAPHICS] .
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