Abstract
Catalytic amination of alkenes is one of the most attractive reactions for the construction of complex heterocycles with nitrogen centers. Herein, we present that synergistic photoredox and cobaloxime catalysis allows for highly efficient and mild dehydrogenative reactions between various NH nucleophiles and di-, tri-, and tetrasubstituted alkenes in the absence of external oxidants, thus enabling access to an array of N-heterocycles. Notably, both Z- and E-alkene-containing N-heterocycles are accessible. Mechanistic studies indicated that the Z-cinnamyl derivatives could be generated by photocatalytic E to Z alkene isomerization through an energy transfer process. Moreover, we find that sluggish energy transfer could inhibit the E to Z alkene isomerization process, thus offering the cinnamyl derivatives with E-selectivity. Our results highlight the benefits of the reactions using dual photoredox and cobaloxime catalysis to lead to diverse N-heterocycles.
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20 September 2022
An Erratum to this paper has been published: https://doi.org/10.1007/s11426-022-1393-1
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Acknowledgements
This work was supported by the Natural Science Foundation of the Jiangsu Higher Education Institutions of China (18KJA350001) and the Priority Academic Program Development of the Jiangsu Higher Education Institutes (PAPD).
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The online version of the original article can be found at https://doi.org/10.1007/s11426-022-1393-1
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Tu, JL., Tang, W., He, SH. et al. Acceptorless dehydrogenative amination of alkenes for the synthesis of N-heterocycles. Sci. China Chem. 65, 1330–1337 (2022). https://doi.org/10.1007/s11426-022-1241-x
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DOI: https://doi.org/10.1007/s11426-022-1241-x