Carbon–nitrogen transmutation in polycyclic arenol skeletons to access N-heteroarenes

Hong Lu, Yu Zhang, Xiu-Hong Wang, Ran Zhang, Peng-Fei Xu () and Hao Wei ()
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Hong Lu: Northwest University
Yu Zhang: Northwest University
Xiu-Hong Wang: Northwest University
Ran Zhang: Northwest University
Peng-Fei Xu: Lanzhou University
Hao Wei: Northwest University

Nature Communications, 2024, vol. 15, issue 1, 1-8

Abstract: Abstract Developing skeletal editing tools is not a trivial task, and realizing the corresponding single-atom transmutation in a ring system without altering the ring size is even more challenging. Here, we introduce a skeletal editing strategy that enables polycyclic arenols, a highly prevalent motif in bioactive molecules, to be readily converted into N-heteroarenes through carbon–nitrogen transmutation. The reaction features selective nitrogen insertion into the C–C bond of the arenol frameworks by azidative dearomatization and aryl migration, followed by ring-opening, and ring-closing (ANRORC) to achieve carbon-to-nitrogen transmutation in the aromatic framework of the arenol. Using widely available arenols as N-heteroarene precursors, this alternative approach allows the streamlined assembly of complex polycyclic heteroaromatics with broad functional group tolerance. Finally, pertinent transformations of the products, including synthesis complex biheteroarene skeletons, were conducted and exhibited significant potential in materials chemistry.

Date: 2024
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DOI: 10.1038/s41467-024-48265-6

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