Harnessing nitroarenes as nitrogen and oxygen sources for general oxo-aminomethylation of alkenes
Ting Zhou1, Jing Nie1, Chi Wai Cheung2,3
1Department of Chemistry, State Key Laboratory of Synthetic Biology, Tianjin University, Tianjin, PR China.
Abstract:
Amino alcohols are essential synthetic building blocks and privileged motifs in drug development, playing a crucial role in modulating pharmacokinetics and biological activity. However, the efficient synthesis of 3-amino alcohols remains challenging compared to their 2-amino counterparts, often requiring multistep procedures, expensive substrates, or highly sensitive reagents. Despite their versatile reactivity in advanced synthesis, nitroarenes remain underutilized as dual nitrogen and oxygen sources. Herein, we report a metallaphotoredox-catalyzed multicomponent oxo-aminomethylation of nitroarenes, tertiary alkylamines, and alkenes, providing a modular and cost-effective route to diverse 3-arylamino alcohols. This strategy features a broad substrate scope, excellent functional group tolerance, and high regioselectivity. The resulting amino alcohols serve as key intermediates for further derivatization, enhancing molecular complexity. By expanding the synthetic utility of nitroarenes, this method offers a practical and efficient pathway to bioactive molecules with pharmaceutical relevance.
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