2026-06-28T15:16:22Zhttps://docta.ucm.es/rest/oai/request
oai:docta.ucm.es:20.500.14352/1334552026-02-28T01:09:39Zcom_20.500.14352_14col_20.500.14352_15
Docta Complutense author Zhou, X. author You, Z. author Wang, B. author Huang, Y. author Fernández, Israel author Xiong, Y. author Fernández López, Israel 2026-02-27T09:03:36Z 2026-02-27T09:03:36Z 2026-02-05 Zhou, Xiang, et al. «Visible-Light-Mediated Lewis Acid-Catalyzed Diradical Hydrogen Atom Transfer Reaction of Bicyclo[1.1.0]Butanes». Journal of the American Chemical Society, vol. 148, n.o 6, febrero de 2026, pp. 6270-79. DOI.org (Crossref), https://doi.org/10.1021/jacs.5c18500. 10.1021/jacs.5c18500 https://hdl.handle.net/20.500.14352/133455 https://doi.org/10.1021/jacs.5c18500 https://pubs.acs.org/doi/10.1021/jacs.5c18500 Nitrogen-containing heterocycles are essential to chemical and life sciences due to their diverse biological activities and functional versatility. However, in contrast to 3D bioisosteres of the benzene ring, analogous bioisosteres of nitrogen-containing heterocycles remain quite limited despite several recent developments, where pyridone, a “central bioisostere” for amide, phenyl, pyridine, pyridine N-oxides, and phenols, should be especially highlighted. Herein, we report an effective route for the divergent synthesis of 3-azabicyclo[3.1.1]heptan-2-ones as promising pyridone bioisosteres from bicycle-butanes (BCBs) via Ir/Lewis acid-catalyzed programmed hydrogen atom transfer of C(sp3)–H bonds and subsequent cyclization under visible light. Mechanistic evidence and DFT calculations suggest that the acid catalyst was crucial for the success via isomerizing BCBs and modulating the reactivity of the diradical intermediates to unlock a challenging carbon-to-carbon DHAT and subsequent cyclization that allows the functionalization of various C(sp3)–H bonds, accessing underexplored 3-azabicyclo[3.1.1]heptan-2-ones. Lastly, further transformations and applications in synthetic chemistry and bioactive molecules reveal their promising potential in organic synthesis, materials science, and pharmaceuticals. eng Visible-Light-Mediated Lewis Acid-Catalyzed Diradical Hydrogen Atom Transfer Reaction of Bicyclo[1.1.0]butanes journal article 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URL https://docta.ucm.es/bitstreams/11621d31-c7d3-4c49-913f-b94cee08d728/download File MD5 e0d692adcd351af5d3c46255dfc66096 3648076 application/pdf JACS2026,148,6270.pdf