Visible light induced alkene aminopyridylation using N-aminopyridinium salts as bifunctional reagents

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The development of intermolecular alkene aminopyridylation has great potential for quickly increasing molecular complexity with two valuable groups. Here we report a strategy for the photocatalytic aminopyridylation of alkenes using a variety of N-aminopyridinium salts as both aminating and pyridylating reagents. Using Eosin Y as a photocatalyst, amino and pyridyl groups are simultaneously incorporated into alkenes, affording synthetically useful aminoethyl pyridine derivatives under mild reaction conditions. Remarkably, the C4-regioselectivity in radical trapping with N-aminopyridinium salt can be controlled by electrostatic interaction between the pyridinium nitrogen and sulfonyl group of β-amino radical. This transformation is characterized by a broad substrate scope, good functional group compatibility, and the utility of this transformation was further demonstrated by late-stage functionalization of complex biorelevant molecules. Combining experiments and DFT calculations on the mechanism of the reaction is investigated to propose a complete mechanism and regioselectivity.
Publisher
NATURE PUBLISHING GROUP
Issue Date
2019-09
Language
English
Article Type
Article
Citation

NATURE COMMUNICATIONS, v.10, no.1

ISSN
2041-1723
DOI
10.1038/s41467-019-12216-3
URI
http://hdl.handle.net/10203/267710
Appears in Collection
CH-Journal Papers(저널논문)
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