公开(公告)号：US20230150919A1

公开(公告)日：2023-05-18

申请号：US17908197

申请日：2021-03-02

申请人： National University Corporation Hokkaido University

发明人： Hajime Ito ,  Koji Kubota

IPC分类号： C07C209/68 ,  C07C41/30 ,  C07C17/263 ,  C07C1/30 ,  C07C17/269 ,  C07D333/16 ,  C07D333/22 ,  C07D333/56 ,  C07C1/32

CPC分类号： C07C209/68 ,  C07C41/30 ,  C07C17/263 ,  C07C1/30 ,  C07C17/269 ,  C07D333/16 ,  C07D333/22 ,  C07D333/56 ,  C07C1/325

摘要： Disclosed is a method for producing a mono-cross-coupled aromatic compound (3-1) having one less leaving group than an aromatic compound (1) having at least two leaving groups, the method comprising: preparing the aromatic compound (1) having at least two leaving groups; preparing a compound (2) capable of undergoing a cross-coupling reaction selected from an aromatic boronic acid (2-1), an aromatic amino compound (2-2), a diboronic acid ester (2-3), an aromatic compound (2-4) having a hydroxyl group and an aromatic compound (2-5) having a thiol group; and performing a cross-coupling reaction of the aromatic compound (1) having at least two leaving groups with the compound (2) in the presence of a palladium catalyst and a base, in the absence of a solvent.

公开(公告)号：US11453678B2

公开(公告)日：2022-09-27

申请号：US17287423

申请日：2019-10-23

申请人： NATIONAL UNIVERSITY CORPORATION HOKKAIDO UNIVERSITY

发明人： Hajime Ito ,  Koji Kubota

IPC分类号： C07D487/22 ,  B01J23/44 ,  C07C17/275 ,  C07C41/22 ,  C07C45/68 ,  C07C67/343 ,  C07C209/10 ,  C07D209/88 ,  C07D333/28 ,  C07D333/36 ,  C07F5/02

摘要： Disclosed is a cross-coupling reaction method which forms a chemical bond selected from C—N, C—B, C—C, C—O and C—S bonds, the method comprising: preparing an aromatic compound (1) having a leaving group; preparing a compound (2) capable of undergoing a cross-coupling reaction selected from an aromatic amino compound (2-1), a diboronic acid ester or the like (2-2), an aromatic boronic acid or the like (2-3), an aromatic compound (2-4) having a hydroxyl group and an aromatic compound (2-5) having a thiol group; and performing a cross-coupling reaction of the compound (1) with the compound (2) in the presence of a palladium catalyst, a base and a compound (4) having a carbon-carbon double bond or a carbon-carbon triple bond, in the absence of a solvent.