Cu-Catalyzed Intermolecular gamma-Site C-H Amination of Cyclohexenone Derivatives: The Benefit of Bifunctional Ligands

Zhao, Xin1,2; Yang, Fang1; Zou, Shao-Yu1; Zhou, Qian-Qian1; Chen, Zi-Sheng1; Ji, Kegong1,3

2022-02-04

10.1021/acscatal.1c05439

ACS Catalysis   影响因子和分区

2155-5435

Utilizing 1,10-phenanthroline-type bifunctional ligands, an efficient Cu-catalyzed intermolecular site-selective remote C-H amination using cyclohexenone derivatives and anilines was realized. The amide group installed on the bifunctional ligand played a key role in stabilizing the N-centered radical generated in situ to realize C-N-directed formation. Meanwhile, a useful catalytic system for site-selective intermolecular remote gamma-C-H amination to p-aminophenols and gamma-aminated enones was established. This economical and practical approach using oxygen as the terminal oxidant was mild and environmentally friendly.

bifunctional ligand Cu-catalyzed N-centered radical cross-coupling remote gamma-C-H amination

SCI ; EI

英语

通讯

National Natural Science Foundation of China["NSF21702170",22171228] ; Guangdong Provincial Key Laboratory of Catalysis[2020B121201002]

Chemistry

Chemistry, Physical

WOS:000753081900013

AMER CHEMICAL SOC

20220411537726

Amides ; Aniline ; Copper compounds ; Ketones ; Ligands

Physical Chemistry:801.4 ; Chemical Reactions:802.2 ; Organic Compounds:804.1

Web of Science

1.Northwest A&F Univ, Coll Chem & Pharm, Xianyang 712100, Shaanxi, Peoples R China
2.Baotou Med Coll, Sch Pharm, Baotou 014060, Inner Mongolia, Peoples R China
3.Southern Univ Sci & Technol, Guangdong Prov Key Lab Catalysis, Shenzhen 518055, Peoples R China

Zhao, Xin,Yang, Fang,Zou, Shao-Yu,et al. Cu-Catalyzed Intermolecular gamma-Site C-H Amination of Cyclohexenone Derivatives: The Benefit of Bifunctional Ligands[J]. ACS Catalysis,2022,12(3):1732-1741.

Zhao, Xin,Yang, Fang,Zou, Shao-Yu,Zhou, Qian-Qian,Chen, Zi-Sheng,&Ji, Kegong.(2022).Cu-Catalyzed Intermolecular gamma-Site C-H Amination of Cyclohexenone Derivatives: The Benefit of Bifunctional Ligands.ACS Catalysis,12(3),1732-1741.

Zhao, Xin,et al."Cu-Catalyzed Intermolecular gamma-Site C-H Amination of Cyclohexenone Derivatives: The Benefit of Bifunctional Ligands".ACS Catalysis 12.3(2022):1732-1741.