Manna Kartic, Ganguly Tanusree, Baitalik Sujoy, Jana Ranjan
Organic and Medicinal Chemistry Division, CSIR-Indian Institute of Chemical Biology 4 Raja S. C. Mullick Road, Jadavpur, Kolkata 700032, West Bengal, India.
Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201 002, Uttar Pradesh, India.
Org Lett. 2021 Nov 5;23(21):8634-8639. doi: 10.1021/acs.orglett.1c03343. Epub 2021 Oct 13.
We present here a metal-free, visible-light- and triphenylphosphine-mediated intermolecular, reductive amination between nitroarenes and boronic acids at ambient temperature without any photocatalyst. Mechanistically, a slow reduction of nitroarenes to a nitroso and, finally, a nitrene intermediate occurs that leads to the amination product with concomitant 1,2-aryl/-alkyl migration from a boronate complex. A wide range of nitroarenes underwent C-N coupling with aryl-/alkylboronic acids providing high yields.
我们在此展示了一种无金属、可见光和三苯基膦介导的分子间还原胺化反应，该反应在室温下于无任何光催化剂的条件下，使硝基芳烃与硼酸发生反应。从机理上讲，硝基芳烃会缓慢还原为亚硝基，最终生成氮烯中间体，该中间体导致胺化产物的生成，并伴随硼酸酯络合物发生1,2-芳基/烷基迁移。多种硝基芳烃与芳基/烷基硼酸发生C-N偶联反应并获得了高产率。
