Efficient and chemoselective imine synthesis catalyzed by a well-defined PN3-manganese(<sc>ii</sc>) pincer system

被引:2
|
作者
Gholap, Sandeep Suryabhan [1 ,2 ]
Al Dakhil, Abdullah [2 ]
Chakraborty, Priyanka [1 ,2 ]
Dighe, Shashikant [3 ,4 ]
Rahman, Mohammad Misbahur [1 ,2 ]
Dutta, Indranil [1 ,2 ]
Hengne, Amol [3 ,4 ]
Huang, Kuo-Wei [1 ,2 ,3 ,4 ]
机构
[1] King Abdullah Univ Sci & Technol KAUST, KAUST Catalysis Ctr, Thuwal 239556900, Saudi Arabia
[2] King Abdullah Univ Sci & Technol, Div Phys Sci & Engn, Thuwal 239556900, Saudi Arabia
[3] Agcy Sci Technol & Res, Inst Mat Res & Engn, Singapore, Singapore
[4] Inst Sustainabil Chem Energy & Environm, Singapore, Singapore
关键词
PRIMARY AMINES; REDUCTIVE AMINATION; C-H; SELECTIVE HYDROGENATION; NITRILES; ALCOHOLS; COMPLEXES; FORM; BENZALDEHYDE; REACTIVITY;
D O I
10.1039/d3cc05892a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The highly efficient reductive amination of aldehydes with ammonia (NH3) and hydrogen (H-2) to form secondary imines is described, as well as the dehydrogenative homocoupling of benzyl amines. Using an air-stable, well-defined PN3-manganese(ii) pincer complex as a catalyst precursor, various aldehydes are easily converted directly into secondary imines using NH3 as a nitrogen source under H-2 in a one-pot reaction. Importantly, the same catalyst facilitates the dehydrogenative homocoupling of various benzylamines, exclusively forming imine products. These reactions are conducted under very mild conditions, without the addition of any additives, yielding excellent selectivities and high yields of secondary imines in a green manner by minimizing wastes.
引用
收藏
页码:2617 / 2620
页数:4
相关论文
共 48 条
  • [1] Efficient and chemoselective hydrogenation of aldehydes catalyzed by well-defined PN3-pincer manganese(ii) catalyst precursors: an application in furfural conversion
    Gholap, Sandeep Suryabhan
    Al Dakhil, Abdullah
    Chakraborty, Priyanka
    Li, Huaifeng
    Dutta, Indranil
    Das, Pradip K.
    Huang, Kuo-Wei
    CHEMICAL COMMUNICATIONS, 2021, 57 (89) : 11815 - 11818
  • [2] Well-defined cobalt(<sc>ii</sc>)-catalyzed synthesis of perimidine derivatives via acceptorless dehydrogenative annulation
    Pal, Debjyoti
    Sarmah, Rajashri
    Mondal, Avijit
    Mallick, Itu
    Srimani, Dipankar
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (43) : 8602 - 8607
  • [3] HIGHLY CHEMOSELECTIVE SYNTHESIS OF BENZIMIDAZOLES IN SC(OTF)3-CATALYZED SYSTEM
    Fan, Liyan
    Kong, Lulu
    Chen, Wen
    HETEROCYCLES, 2015, 91 (12) : 2306 - 2314
  • [4] Switchable Imine and Amine Synthesis Catalyzed by a Well-Defined Cobalt Complex
    Paudel, Keshav
    Xu, Shi
    Hietsoi, Oleksandr
    Pandey, Bedraj
    Onuh, Chuka
    Ding, Keying
    ORGANOMETALLICS, 2021, 40 (03) : 418 - 426
  • [5] Electrocatalytic Reduction of Carbon Dioxide with a Well-Defined PN3-Ru Pincer Complex
    Min, Shixiong
    Rasul, Shahid
    Li, Huaifeng
    Grills, David C.
    Takanabe, Kazuhiro
    Li, Lain-Jong
    Huang, Kuo-Wei
    CHEMPLUSCHEM, 2016, 81 (02): : 166 - 171
  • [6] A well-defined phosphine-free metal-ligand cooperative route for N-alkylation of aromatic amines via activation of renewable alcohols catalyzed by NNN pincer cobalt(<sc>ii</sc>) complexes
    Saini, Rahul
    Kukreti, Prashant
    Chauhan, Rahul
    Panwar, Abhishek
    Ghosh, Kaushik
    DALTON TRANSACTIONS, 2025, 54 (14) : 5838 - 5848
  • [7] Efficient Hydrogenation of Ketones and Aldehydes Catalyzed by Well-Defined Iron(II) PNP Pincer Complexes: Evidence for an Insertion Mechanism
    Gorgas, Nikolaus
    Stoeger, Berthold
    Veiros, Luis F.
    Pittenauer, Ernst
    Allmaier, Guenter
    Kirchner, Karl
    ORGANOMETALLICS, 2014, 33 (23) : 6905 - 6914
  • [8] Well-Defined Phosphine-Free Manganese(II)-Complex-Catalyzed Synthesis of Quinolines, Pyrroles, and Pyridines
    Maji, Ankur
    Gupta, Shivangi
    Maji, Milan
    Kundu, Sabuj
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (13): : 8351 - 8367
  • [9] Chemoselective transfer hydrogenation of aldehydes in aqueous media catalyzed by a well-defined iron(II) hydride complex
    Gorgas, Nikolaus
    Ilic, Aleksandra
    Kirchner, Karl
    MONATSHEFTE FUR CHEMIE, 2019, 150 (01): : 121 - 126
  • [10] Chemoselective transfer hydrogenation of aldehydes in aqueous media catalyzed by a well-defined iron(II) hydride complex
    Nikolaus Gorgas
    Aleksandra Ilic
    Karl Kirchner
    Monatshefte für Chemie - Chemical Monthly, 2019, 150 : 121 - 126