Synthesis of N-alkoxy amines and hydroxylamines via the iridium-catalyzed transfer hydrogenation of oximes

被引：12
|
作者：
Xia, Yanping [2 ]
Wang, Sen [2 ]
Miao, Rui [2 ]
Liao, Jianhua [1 ,2 ]
Ouyang, Lu [2 ]
Luo, Renshi [1 ,2 ]
机构：
[1] Shaoguan Univ, Coll Chem & Environm Engn, Shaoguan 512005, Peoples R China
[2] Gannan Med Univ, Sch Pharmaceut Sci, Ganzhou, Jiangxi, Peoples R China
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2022年 / 20卷 / 32期
基金：
中国国家自然科学基金;
关键词：
ASYMMETRIC TRANSFER HYDROGENATION; ENANTIOSELECTIVE HYDROGENATION; REDUCTION; KETONES; LIGAND; COMPLEX; ETHERS; NANOPARTICLES; MECHANISM; OXIDATION;
D O I：
10.1039/d2ob01084d
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Cationic iridium (Ir) complexes were found to catalyze the transfer hydrogenation of oximes to access N-alkoxy amines and hydroxylamines, and the reaction was accelerated by trifluoroacetic acid. The practical application of this protocol was demonstrated by a gram-scale transformation and two-step synthesis of the fungicide furmecyclox (BAS 389F) in overall yields of 92 and 85%, respectively. An asymmetric protocol using chiral Ir complexes to afford chiral N-alkoxy amines was demonstrated, but the low yields/ee obtained indicated that further development was required.
引用
收藏
页码：6394 / 6399
页数：6
相关论文
共 50 条
  • [31] Synthesis of Chiral γ-Lactams via in Situ Elimination/Iridium-Catalyzed Asymmetric Hydrogenation of Racemic γ-Hydroxy γ-Lactams
    Yuan, Qianjia
    Liu, Delong
    Zhang, Wanbin
    ORGANIC LETTERS, 2017, 19 (07) : 1886 - 1889
  • [32] Iridium-Catalyzed Asymmetric Hydrogenation of Olefins with Chiral N,P and C,N Ligands
    Woodmansee, David H.
    Pfaltz, Andreas
    IRIDIUM CATALYSIS, 2011, 34 : 31 - +
  • [33] Catalytic Enantioselective Desymmetrization of Meso Cyclic Anhydrides via Iridium-Catalyzed Hydrogenation
    Liu, Tang-Lin
    Li, Wei
    Geng, Huiling
    Wang, Chun-Jiang
    Zhang, Xumu
    ORGANIC LETTERS, 2013, 15 (07) : 1740 - 1743
  • [34] Iridium-Catalyzed Single-Step N-Substituted Lactam Synthesis from Lactones and Amines
    Kim, Kicheol
    Hong, Soon Hyeok
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (08): : 4152 - 4156
  • [35] Synthesis of benzimidazoles via iridium-catalyzed acceptorless dehydrogenative coupling
    Sun, Xiang
    Lv, Xiao-Hui
    Ye, Lin-Miao
    Hu, Yu
    Chen, Yan-Yan
    Zhang, Xue-Jing
    Yan, Ming
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (27) : 7381 - 7383
  • [36] Mechanistic study on the Cp*iridium-catalyzed N-alkylation of amines with alcohols
    Zhao, Guo-Ming
    Liu, Hui-ling
    Huang, Xu-ri
    Zhang, Dan-dan
    Yang, Xue
    RSC ADVANCES, 2015, 5 (29) : 22996 - 23008
  • [37] Highly Efficient and Enantioselective Iridium-Catalyzed Asymmetric Hydrogenation of N-Arylimines
    Li, Wei
    Hou, Guohua
    Chang, Mingxin
    Zhang, Xumu
    ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (18) : 3123 - 3127
  • [38] Highly Enantioselective Synthesis of Optically Active Ketones by Iridium-Catalyzed Asymmetric Hydrogenation
    Liu, Sheng-Mei
    Bolm, Carsten
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (46) : 8920 - 8923
  • [39] Iridium-Catalyzed Asymmetric Transfer Hydrogenation of 1-Aryl-1-alkylethenes with Ethanol
    Tang, Xixia
    Qian, Lu
    Liu, Guixia
    Huang, Zheng
    ORGANIC LETTERS, 2023, 25 (26) : 4950 - 4954
  • [40] Iridium-catalyzed transfer hydrogenation of α,β-unsaturated and saturated carbonyl compounds with 2-propanol
    Sakaguchi, S
    Yamaga, T
    Ishii, Y
    JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (13): : 4710 - 4712
12345