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Expedient access to saturated nitrogen heterocycles by photoredox cyclization of imino-tethered dihydropyridines

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Abstract

A large proportion of medicinally relevant molecules bear nitrogen and sp3-hybridized carbon functionalities. Overwhelmingly, these atoms are found as part of (hetero)cyclic structures. Despite their importance, synthetic approaches to saturated nitrogen heterocycles are limited to several established stoichiometric alkylation techniques, as well as a few methods involving C–H bond activation. The synthetic community remains interested in more general, mild, and sustainable ways to access these motifs. Here we describe a dual-catalyst system composed of an iridium photocatalyst and a lithium phosphate base that is capable of selectively homolyzing the N–H bond of 4-alkyl-1,4-dihydropyridines, presumably by proton-coupled-electron-transfer (PCET), and mediating efficient cyclization of the resultant carbon-centered radicals with tethered imines. The outcome of this transformation is access to a broad range of structurally complex nitrogen heterocycles obtainable from simple aldehyde starting materials in a highly chemoselective manner.

Graphical abstract: Expedient access to saturated nitrogen heterocycles by photoredox cyclization of imino-tethered dihydropyridines

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Publication details

The article was received on 11 Jul 2019, accepted on 26 Aug 2019 and first published on 28 Aug 2019


Article type: Edge Article
DOI: 10.1039/C9SC03429C
Chem. Sci., 2019, Advance Article
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    Expedient access to saturated nitrogen heterocycles by photoredox cyclization of imino-tethered dihydropyridines

    N. B. Bissonnette, J. M. Ellis, L. G. Hamann and F. Romanov-Michailidis, Chem. Sci., 2019, Advance Article , DOI: 10.1039/C9SC03429C

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