期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 27, 期 11, 页码 3855-3860出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202004881
关键词
catalysis; computations; directing group; mechanistic study; palladium
资金
- NSERC Canada [RGPIN-2018-05584]
- Eli Lilly Research Award Program (LRAP)
Two similar tridentate directing groups derived from glycine and 8-aminoquinoline showed significantly different efficiencies in the palladium-catalyzed anti-Markovnikov hydrofunctionalization of 4-pentenylamine. Computational investigation revealed that the protonation state and charge of the substrate-metal complex prior to nucleopalladation are crucial for the reactivity difference between these isomeric auxiliaries. These findings led to the design of a directing group that can undergo Pd-catalyzed hydrofunctionalization under relatively mild conditions, down to room temperature.
Two similar tridentate directing groups derived from glycine and 8-aminoquinoline were shown to enable the palladium-catalyzed anti-Markovnikov hydrofunctionalization of 4-pentenylamine with drastically different efficiencies. A computational investigation into the origin of the reactivity difference between these isomeric, carbonyl-transposed auxiliaries suggests that protonation state, thus charge of the substrate-metal complex prior to nucleopalladation is key. These investigations have culminated in a directing group design that can undergo Pd-catalyzed hydrofunctionalization under relatively mild conditions, as low as room temperature.
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