Regio- and Enantioselective Nickel-Catalyzed Ipso- and Remote Hydroamination Utilizing Organic Azides as Amino Sources for the Synthesis of Primary Amines

被引：1

作者：

Wang, Shi-Chao ^{[1
]}

Liu, Lin ^{[2
]}

Duan, Mei ^{[1
]}

Xie, Weijia ^{[1
]}

Han, Jiabin ^{[1
]}

Xue, Yuhang ^{[1
]}

Wang, You ^{[1
]}

Wang, Xiaotai ^{[2
]}

Zhu, Shaolin ^{[1
,3
,4
]}

机构：

[1] Nanjing Univ, Chem & Biomed Innovat Ctr ChemB, Sch Chem & Chem Engn, State Key Lab Coordinat Chem,Jiangsu Key Lab Adv O, Nanjing 210093, Peoples R China

[2] Xian Jiaotong Liverpool Univ, Dept Chem, Suzhou 215123, Peoples R China

[3] Henan Normal Univ, Sch Chem & Chem Engn, Xinxiang 453007, Peoples R China

[4] Shanghai Jiao Tong Univ, Shanghai Key Lab Mol Engn Chiral Drugs, Shanghai 200240, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2024年 / 146卷 / 44期

基金：

中国国家自然科学基金; 国家重点研发计划;

关键词：

ANTI-MARKOVNIKOV HYDROAMINATION; ALKYL-ARYL KETONES; UNACTIVATED ALKENES; REDUCTIVE AMINATION; INTERMOLECULAR HYDROAMINATION; ASYMMETRIC-SYNTHESIS; ACCESS; HYDROAMIDATION; MILD; FUNCTIONALIZATION;

D O I：

10.1021/jacs.4c12324

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Primary amines serve as key synthetic precursors to most other N-containing compounds, which are important in organic and medicinal chemistry. Herein, we present a NiH-catalyzed mild ipso- and remote hydroamination technique that utilizes organic azides as deprotectable primary amine sources. This strategy offers a highly flexible platform for the efficient construction of alpha-chiral branched primary amines, as well as linear primary amines.

引用

页码：30626 / 30636

页数：11

共 4 条

[1] Nickel-Catalyzed Regio- and Enantioselective Hydroamination of Unactivated Alkenes Using Carbonyl Directing Groups
Lee, Changseok
Kang, Hyung-Joon
Seo, Huiyeong
Hong, Sungwoo
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (20) : 9091 - 9100
[2] Nickel-Catalyzed Regio- and Enantioselective Ring Opening of 3,4-Epoxy Amides and Esters with Aromatic Amines
Liu, Jiawei
Tang, Wei
Wang, Chuan
CHEMISTRY-A EUROPEAN JOURNAL, 2023, 29 (31)
[3] Synthesis of α-N-Heteroaryl Ketones by Nickel-Catalyzed Chemo-, Regio- and Enantioselective Carbonylation of Alkenes and N-Alkenyl Heteroarenes
Chen, Xiao-Yi
Yu, Qiong
Shu, Wei
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2025,
[4] Tetrabutylammonium peroxydisulfate in organic synthesis. Part 8. An efficient and convenient nickel-catalyzed oxidation of primary amines to nitriles with tetrabutylammonium peroxydisulfate
Chen, FE
Peng, ZZ
Fu, H
Liu, JD
Shao, LY
JOURNAL OF CHEMICAL RESEARCH, 1999, (12) : 726 - 727

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