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Dhital, Raghu N.; Sen, Abhijit; Hu, Hao; Ishii, Rikako; Sato, Takuma; Yashiroda, Yoko; Kimura, Hiromi; Boone, Charles; Yoshida, Minoru; Futamura, Yushi; Hirano, Hiroyuki; Osada, Hiroyuki; Hashizume, Daisuke; Uozumi, Yasuhiro; Yamada, Yoichi M.A.
ACS omega, 07/2022, Volume: 7, Issue: 28Journal Article
In this study, a phenylboronic ester-activated aryl iodide-selective Buchwald–Hartwig-type amination was developed. When the reaction of aryl iodides and aryl/aliphatic amines using Ni(acac)2 is carried out in the presence of phenylboronic ester, the Buchwald–Hartwig-type amination proceeds smoothly to afford the corresponding amines in high yields. This reaction does not proceed in the absence of phenylboronic ester. A wide variety of aryl iodides can be applied in the presence of aryl chlorides and bromides, which remain intact during the reaction. The mechanistic studies of this reaction suggest that the phenylboronic ester acts as an activator for the amines to form the ″ate complex″. Chemical kinetics studies show that the reaction of aryl iodides, base, and Ni(acac)2 follows first-order kinetics, while that of amines and phenylboronic ester follows zero-order kinetics. The bioactivity screening of the corresponding products showed that some amination products exhibit antifungal activity.
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