Selective Nitrone Synthesis via Cascade Hydrogenative Coupling of Nitro Compounds and Aldehydes Catalyzed by
Taisei Senzaki1, Tomohiro Yasukawa1,2, Yasuhiro Yamashita1
1Department of Chemistry, School of Science, The University of Tokyo, Hongo, Bunkyo-Ku, Tokyo 113-0033, Japan.
Abstract:
Single-atom catalysts have emerged as powerful platforms for selective hydrogenation reactions owing to their well-regulated active sites; however, their unique reactivity in cascade hydrogenation processes remains relatively unexplored. Herein, we report that a single-atom platinum catalyst supported on N,P-doped carbon efficiently catalyzes the cascade hydrogenative coupling of nitro compounds and aldehydes, leading to the highly selective synthesis of nitrones. This catalytic system enables the facile production of 40 diverse nitrones, including those derived from aromatic and aliphatic substrates, as well as important intermediates of bioactive compounds. In sharp contrast to nanoparticle catalysts that promote over-reduction, this Pt single-atom platform exhibits broad functional-group tolerance, accommodating reducible C═C and C═O bonds and aryl halides. Furthermore, the catalyst demonstrates robust durability in a continuous-flow system, providing an atom-economical and sustainable methodology for nitrone synthesis.
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