N-H imines are synthetically versatile but sensitive intermediates in organic synthesis. This work introduces a cascade synthesis of basic amines through N-H imine intermediates, featuring an efficient aza-Norrish Type II fragmentation, followed by photoalkylation. Our method selectively converts bench-stable phenacylamines to α-quaternary primary amines in one pot using mild and metal-free UV photocatalysis. Our work constitutes a rare use of amine photofragmentation in organic synthesis.
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Qingqing Dong
Lizhe He
Adam Czader
The Journal of Organic Chemistry
University of Houston
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Dong et al. (Tue,) studied this question.
www.synapsesocial.com/papers/69a75ab2c6e9836116a20d95 — DOI: https://doi.org/10.1021/acs.joc.5c03147