Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 61, Issue 29, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202204516
Keywords
Photoredox Catalysis; Umpolung; Radical Reactions; Dienes; Allylic Compounds
Categories
Funding
- National Natural Science Foundation of China [2217010858]
- Open Research Fund of School of Chemistry and Chemical Engineering, Henan Normal University [2020YB03]
- Key Scientific Research Projects of Higher Education Institutions in Henan Province [21A150002]
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In this study, we present a metal-free radical cross-coupling strategy for the synthesis of homoallyl amines. This method involves the reaction between an alpha-amino alkyl radical and a transient allylic radical to obtain homoallyl amines from readily available materials. The method exhibits excellent regioselectivity and broad functional group compatibility.
Ionic (2 e(-)) nucleophilic addition of allylmetal regents to imines dominates the synthesis of homo-allyl amine; however, single electron (1 e(-)) mediated imine allylation with feedstocks butadiene as an alternative allyl source remains unexplored. In this work, we report a conceptually different radical-radical cross-coupling strategy for the synthesis of a homoallyl amine between an alpha-amino alkyl radical and a transient allylic radical. This metal-free method provided a novel approach for the synthesis of homoallylic amines (>80 examples) from readily available materials with excellent regioselectivity and exceptional broad functional group compatibility.
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