Visible-Light-Induced 1,3-Aminopyridylation of [1.1.1]Propellane with N-Aminopyridinium Salts

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Through the formation of an electron donor-acceptor (EDA) complex, strain-release aminopyridylation of [1.1.1]propellane with N-aminopyridinium salts as bifunctional reagents enabled the direct installation of amino and pyridyl groups onto bicyclo[1.1.1]pentane (BCP) frameworks in the absence of an external photocatalyst. The robustness of this method to synthesize 1,3-aminopyridylated BCPs under mild and metal-free conditions is highlighted by the late-stage modification of structurally complex biorelevant molecules. Moreover, the strategy was extended to P-centered and CF3 radicals for the unprecedented incorporation of such functional groups with pyridine across the BCP core in a three-component coupling. This practical method lays the foundation for the straightforward construction of new valuable C4-pyridine-functionalized BCP chemical entities, thus significantly expanding the range of accessibility of BCP-type bioisosteres for applications in drug discovery.
Publisher
WILEY-V C H VERLAG GMBH
Issue Date
2021-03
Language
English
Article Type
Article
Citation

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v.60, pp.7873 - 7879

ISSN
1433-7851
DOI
10.1002/anie.202016156
URI
http://hdl.handle.net/10203/282209
Appears in Collection
CH-Journal Papers(저널논문)
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