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

Yonghoon Moon, Bohyun Park, Inwon Kim, Gyumin Kang, Sanghoon Shin, Dahye Kang, Mu-Hyun Baik () and Sungwoo Hong ()
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Yonghoon Moon: Korea Advanced Institute of Science and Technology (KAIST)
Bohyun Park: Korea Advanced Institute of Science and Technology (KAIST)
Inwon Kim: Korea Advanced Institute of Science and Technology (KAIST)
Gyumin Kang: Korea Advanced Institute of Science and Technology (KAIST)
Sanghoon Shin: Korea Advanced Institute of Science and Technology (KAIST)
Dahye Kang: Korea Advanced Institute of Science and Technology (KAIST)
Mu-Hyun Baik: Korea Advanced Institute of Science and Technology (KAIST)
Sungwoo Hong: Korea Advanced Institute of Science and Technology (KAIST)

Nature Communications, 2019, vol. 10, issue 1, 1-9

Abstract: Abstract 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.

Date: 2019
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DOI: 10.1038/s41467-019-12216-3

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