3 years ago

[ASAP] Synthesis of Diverse Boron-Handled N-Heterocycles via Radical Borylative Cyclization of N-Allylcyanamides

[ASAP] Synthesis of Diverse Boron-Handled N-Heterocycles via Radical Borylative Cyclization of N-Allylcyanamides
Ji-Kang Jin, Feng-Lian Zhang, Qiang Zhao, Jun-An Lu, Yi-Feng Wang
A synthetic method based on radical borylation/cyclization cascades of N-allylcyanamides was developed to construct diverse boron-substituted N-heterocycles. In the reaction process, the N-heterocyclic carbene–boryl radical underwent a chemo- and regioselective addition to the alkene moiety, followed by cyclization with the N-cyano group. The resulting amide–iminyl radical intermediates underwent further reactions to afford various boron-tethered N-heterocyclic molecules. Further transformations to access synthetically useful building blocks were also demonstrated.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.8b03303

DOI: 10.1021/acs.orglett.8b03303

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