Transition-metal-free, three-component trifluoromethylative heteroarylation of unactivated alkenes: Efficient access to β-trifluoromethylated quinoxalinones and preliminary antifungal evaluation against Magnaporthe grisea
2020; Elsevier BV; Volume: 76; Issue: 22 Linguagem: Inglês
10.1016/j.tet.2020.131199
ISSN1464-5416
AutoresZhuoxian Shao, Shaoyi Zhang, Yihan Chen, Yun‐Lin Liu, Ri‐Yuan Tang, Zhaodong Li,
Tópico(s)Catalytic C–H Functionalization Methods
ResumoHerein, a transition-metal-free trifluoromethylative heteroarylation of unactivated alkenes is presented by employing CF3SO2Na and quinoxalin-2(1H)-ones as coupling partners and PhI(OAc)2 as oxidant. This three-component radical domino reaction allows an efficient synthesis of valuable β-trifluoromethyl alkyl quinoxalinones derivatives in a single step in moderate to excellent yields under mild conditions. Mechanistic studies indicated the cascade radical addition pathway controlled by radical polar. This three-component strategy readily affords synthetically and biologically important trifluoromethyl- and quinoxalinones -containing framework, which has been demonstrated by the preliminary antibacterial evaluation against Magnaporthe grisea for the first time.
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