TY  - JOUR
AB  - 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 π-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 π-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.
AU  - Huang, Huan-Ming
AU  - Koy, Maximilian
AU  - Serrano, Eloisa
AU  - Pflüger, Philipp Miro
AU  - Schwarz, J. Luca
AU  - Glorius, Frank
DA  - 2020
KW  - Homogeneous catalysis
KW  - Synthetic chemistry methodology
KW  - Photocatalysis
KW  - Reaction mechanisms
LA  - eng
N1  - Supplementary information is available in the published version of the paper: https://doi.org/10.1038/s41929-020-0434-0
N1  - This document is the author’s final version of a published work that appeared in final form in Nature Catalysis (ISSN 2520-1158) after technical editing by the publisher. To access the final edited and published work, see https://doi.org/10.1038/s41929-020-0434-0
PY  - 2020
TI  - Catalytic radical generation of π-allylpalladium complexes
UR  - https://nbn-resolving.org/urn:nbn:de:hbz:6-81169738730
Y2  - 2024-11-21T23:31:03
ER  -