期刊
NATURE CATALYSIS
卷 3, 期 4, 页码 393-400出版社
NATURE PUBLISHING GROUP
DOI: 10.1038/s41929-020-0434-0
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资金
- Alexander von Humboldt Foundation
- European Union [843349-H2020-MSCA-IF-2018]
- Deutsche Forschungsgemeinschaft [SFB 858]
Transition metal catalysed allylic substitution is one of the most powerful and frequently used methods in organic synthesis. In particular, palladium-catalysed allylic functionalization has become a well-established strategy for constructing carbon-carbon or carbon-heteroatom bonds, and its utility has been demonstrated in natural product synthesis, drug discovery and materials science. Several methods have been developed to generate pi-allylpalladium complexes through ionic mechanisms; however, these methods typically require either prefunctionalized starting materials or stoichiometric oxidants, which naturally limits their scope. Here, we show a radical approach for the generation of pi-allylpalladium complexes by employing N-hydroxyphthalimide esters as bifunctional reagents in combination with 1,3-dienes. Using this strategy, we report the 1,4-aminoalkylation of dienes. The remarkable scope and functional group tolerance of this redox-neutral and mild protocol was demonstrated across >60 examples. The utility of this strategy was further demonstrated in radical cascade reactions and in the late-stage modification of drugs and natural products.
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