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

Overview

Journal ACS Omega

Publisher American Chemical Society

Specialty Chemistry

Date 2022 Jul 25

PMID 35874269

Authors

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

Affiliations

Soon will be listed here.

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) 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) 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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PMID: 38950197 PMC: 11267615. DOI: 10.1021/acs.joc.4c01220.

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