Visible-light-catalyzed synthesis of amino alcohols from N,N-dimethylaniline and aryl aldehyde

被引:0
|
作者
Jin, Jia-Hui [1 ]
Ma, Yi-Jian [1 ]
Yin, Yu-Yun [1 ]
Zhao, Fu-Gang [1 ,2 ]
Shen, Cheng-Shuo [1 ,2 ]
Xu, Cheng-Miao [3 ]
Shen, Yong-Miao [1 ,2 ]
机构
[1] Zhejiang Sci Tech Univ, Sch Chem & Chem Engn, Key Lab Surface & Interface Sci Polymer Mat Zhejia, Hangzhou 310018, Zhejiang, Peoples R China
[2] Zhejiang Sci Tech Univ, Shengzhou Innovat Res Inst, Shengzhou 312400, Peoples R China
[3] Zhejiang Anglikang Pharmaceut Co Ltd, Shengzhou 312400, Peoples R China
关键词
Visible-light mediate; amino alcohols; continuous flow; PHOTOREDOX; HYDROXYAMINES; DERIVATIVES; ADDITIONS; RADICALS;
D O I
10.1093/chemle/upae112
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Herein, we describe a direct radical addition reaction of aryl aldehyde and N, N-dimethylaniline using iridium complex as photocatalyst to form amino alcohols under mild conditions, offering a convenient and sustainable methodology. The reaction could be easily scaled up through continuous flow reaction with high yield. A series of amino alcohol compounds were synthesized with iridium complex as photocatalyst. The reaction could be scaled up with continuous flow reaction. The reaction mechanism has been investigated with the aid of density functional theory (DFT) calculations. Graphical Abstract A direct radical addition reaction of aryl aldehyde and N, N-dimethylaniline to synthesize of amino alcohols compounds under mild conditions, and can be easily scale-up through continuous flow.
引用
收藏
页数:4
相关论文
共 50 条
  • [41] ENTHALPIES OF TRANSFER OF N,N-DIMETHYLANILINE AND OF ANILINE FROM WATER PLUS HEXAMETHYLPHOSPHOROTRIAMIDE (HMPT)
    AVEDIKIAN, L
    GELINAS, N
    PERRON, G
    DESNOYERS, JE
    JOURNAL DE CHIMIE PHYSIQUE ET DE PHYSICO-CHIMIE BIOLOGIQUE, 1984, 81 (02) : 95 - 97
  • [43] A new radical way to N,N-dimethylaniline hydroperoxide (DMAHP) and its application in organic synthesis
    Xu, Yi
    Zhang, Shi Lei
    Duan, Wen Hu
    CHINESE CHEMICAL LETTERS, 2007, 18 (07) : 807 - 810
  • [44] Vapor-Liquid Equilibrium for the Binary System of N,N-Dimethylaniline with 2-Amino-3-methylpyridine
    Zeng, Zuo-xiang
    Kong, Qing-juan
    Xue, Wei-lan
    Yuan, Xiong-jun
    JOURNAL OF CHEMICAL AND ENGINEERING DATA, 2011, 56 (03): : 551 - 555
  • [45] Morphology dependent photoinduced electron transfer from N,N-dimethylaniline to semiconductor cadmium sulfide
    Chakrabarty, Sankalpita
    Kaur, Harveen
    Pal, Tanusri
    Kar, Soumitra
    Ghosh, Surajit
    Ghosh, Subhadip
    RSC ADVANCES, 2014, 4 (67) : 35531 - 35540
  • [46] SYNTHESIS AND REACTIONS OF NUCLEOPHILIC COMPLEXES OF RHODIUM(I) CONTAINING ORTHO-(DIPHENYLPHOSPHINO)-N,N-DIMETHYLANILINE
    RAUCHFUSS, TB
    ROUNDHIL.DM
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (10) : 3098 - 3105
  • [47] Synthesis, linear and quadratic nonlinear optical properties of ionic indoline and N,N-dimethylaniline based chromophores
    Teshome, Ayele
    Bhuiyan, M. Delower H.
    Gainsford, Graeme J.
    Ashraf, M.
    Asselberghs, Inge
    Williams, Grant V. M.
    Kay, Andrew J.
    Clays, Koen
    OPTICAL MATERIALS, 2011, 33 (03) : 336 - 345
  • [48] Friedel-Crafts Reaction of N,N-Dimethylaniline with Alkenes Catalyzed by Cyclic Diaminocarbene-Gold(I) Complex
    Hangzhi Wu
    Tianxiang Zhao
    Xingbang Hu
    Scientific Reports, 8
  • [49] Iron(III) picolinate-catalyzed oxidative demethylation of N,N-dimethylaniline with hydrogen peroxide in the presence of acetic anhydride
    Kotani, E
    Takeya, T
    Shimizu, H
    Egawa, H
    Yamamoto, T
    Tobinaga, S
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1997, 45 (12) : 2089 - 2092
  • [50] Friedel-Crafts Reaction of N,N-Dimethylaniline with Alkenes Catalyzed by Cyclic Diaminocarbene-Gold(I) Complex
    Wu, Hangzhi
    Zhao, Tianxiang
    Hu, Xingbang
    SCIENTIFIC REPORTS, 2018, 8