Phenylboronic Ester-Activated Aryl Iodide-Selective Buchwald-Hartwig-Type Amination toward Bioactivity Assay

Raghu N. Dhital; Abhijit Sen; Hao Hu; Rikako Ishii; Takuma Sato; Yoko Yashiroda; Hiromi Kimura; Charles Boone; Minoru Yoshida; Yushi Futamura; Hiroyuki Hirano; Hiroyuki Osada; Daisuke Hashizume; Yasuhiro Uozumi; Yoichi M.A. Yamada

doi:10.1021/acsomega.2c01092

Phenylboronic Ester-Activated Aryl Iodide-Selective Buchwald-Hartwig-Type Amination toward Bioactivity Assay

Raghu N. Dhital, Abhijit Sen, Hao Hu, Rikako Ishii, Takuma Sato, Yoko Yashiroda, Hiromi Kimura, Charles Boone, Minoru Yoshida, Yushi Futamura, Hiroyuki Hirano, Hiroyuki Osada, Daisuke Hashizume, Yasuhiro Uozumi^*, Yoichi M.A. Yamada^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

1 Citation (Scopus)

Abstract

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)₂is 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)₂follows 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.

Original language	English
Pages (from-to)	24184-24189
Number of pages	6
Journal	ACS Omega
Volume	7
Issue number	28
DOIs	https://doi.org/10.1021/acsomega.2c01092
Publication status	Published - 2022 Jul 19
Externally published	Yes

ASJC Scopus subject areas

Chemistry(all)
Chemical Engineering(all)

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Dhital, R. N., Sen, A., Hu, H., Ishii, R., Sato, T., Yashiroda, Y., Kimura, H., Boone, C., Yoshida, M., Futamura, Y., Hirano, H., Osada, H., Hashizume, D., Uozumi, Y., & Yamada, Y. M. A. (2022). Phenylboronic Ester-Activated Aryl Iodide-Selective Buchwald-Hartwig-Type Amination toward Bioactivity Assay. ACS Omega, 7(28), 24184-24189. https://doi.org/10.1021/acsomega.2c01092

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title = "Phenylboronic Ester-Activated Aryl Iodide-Selective Buchwald-Hartwig-Type Amination toward Bioactivity Assay",

abstract = "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)2is 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)2follows 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.",

author = "Dhital, {Raghu N.} and Abhijit Sen and Hao Hu and Rikako Ishii and Takuma Sato and Yoko Yashiroda and Hiromi Kimura and Charles Boone and Minoru Yoshida and Yushi Futamura and Hiroyuki Hirano and Hiroyuki Osada and Daisuke Hashizume and Yasuhiro Uozumi and Yamada, {Yoichi M.A.}",

year = "2022",

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doi = "10.1021/acsomega.2c01092",

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T1 - Phenylboronic Ester-Activated Aryl Iodide-Selective Buchwald-Hartwig-Type Amination toward Bioactivity Assay

AU - Dhital, Raghu N.

AU - Sen, Abhijit

AU - Hu, Hao

AU - Ishii, Rikako

AU - Sato, Takuma

AU - Yashiroda, Yoko

AU - Kimura, Hiromi

AU - Boone, Charles

AU - Yoshida, Minoru

AU - Futamura, Yushi

AU - Hirano, Hiroyuki

AU - Osada, Hiroyuki

AU - Hashizume, Daisuke

AU - Uozumi, Yasuhiro

AU - Yamada, Yoichi M.A.

PY - 2022/7/19

Y1 - 2022/7/19

N2 - 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)2is 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)2follows 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.

AB - 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)2is 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)2follows 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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DO - 10.1021/acsomega.2c01092

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JO - ACS Omega

JF - ACS Omega

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Phenylboronic Ester-Activated Aryl Iodide-Selective Buchwald-Hartwig-Type Amination toward Bioactivity Assay

Abstract

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