Synthesis of Selectively Mono-N-Arylated Aliphatic Diamines via Iridium-Catalyzed Amine Alkylation

被引：105
|
作者：
Blank, Benoit [1 ]
Michlik, Stefan [1 ]
Kempe, Rhett [1 ]
机构：
[1] Univ Bayreuth, Lehrstuhl Anorgan Chem 2, D-95440 Bayreuth, Germany
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2009年 / 351卷 / 17期
关键词：
amine alkylation; amino alcohols; diamines; iridium; ASTERISK-IR COMPLEX; BORROWING HYDROGEN; REDUCTIVE AMINATION; TERTIARY-AMINES; ALCOHOLS; SECONDARY; HYDROAMINATION; HETEROCYCLIZATION; ACTIVATION; COORDINATION;
D O I：
10.1002/adsc.200900548
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A highly selective phosphorus/nitrogen (P,N) ligand-based iridium catalyst system efficiently catalyzes the reaction of arylamines with unprotected amino alcohols, yielding N-arylated aliphatic diamines in yields of up to 93%. The reaction can be performed with a wide variety of branched and linear amino alcohols in combination with various aminopyridines or substituted anilines.
引用
收藏
页码：2903 / 2911
页数：9
相关论文
共 50 条
  • [21] Efficient synthesis of chiral β-hydroxy sulfones via iridium-catalyzed hydrogenation
    Tao, Lin
    Yin, Congcong
    Dong, Xiu-Qin
    Zhang, Xumu
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (04) : 785 - 788
  • [22] Iridium-Catalyzed Enantioselective and Chemodivergent Allenylic Alkylation of Vinyl Azides for the Synthesis of α-Allenylic Amides and Ketones
    Chakrabarty, Aditya
    Mukherjee, Santanu
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (12)
  • [23] Asymmetric N-Allylation of Indoles Through the Iridium-Catalyzed Allylic Alkylation/Oxidation of Indolines
    Liu, Wen-Bo
    Zhang, Xiao
    Dai, Li-Xin
    You, Shu-Li
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (21) : 5183 - 5187
  • [24] Mono-N-Alkylation of Sulfonamides with Alcohols Catalyzed by Iridium N-Heterocyclic Carbene-Phosphine Complexes
    Li, Xingzhen
    Peters, Bram B. C.
    Tan, Min
    He, Lei
    Yang, Jianping
    Andersson, Pher G.
    Zhou, Taigang
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 11 (07)
  • [25] Enantioselective modular synthesis of 2,4-disubstituted cyclopentenones by iridium-catalyzed allylic alkylation
    Schelwies, M
    Dübon, P
    Helmchen, G
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (15) : 2466 - 2469
  • [26] Enantioselective Synthesis of Acyclic α-Quaternary Carboxylic Acid Derivatives through Iridium-Catalyzed Allylic Alkylation
    Shockley, Samantha E.
    Hethcox, J. Caleb
    Stoltz, Brian M.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (38) : 11545 - 11548
  • [27] Iridium-Catalyzed Selective Synthesis of 4-Substituted Benzofurans and Indoles via Directed Cyclodehydration
    Tsuchikama, Kyoji
    Hashimoto, Yu-ki
    Endo, Kohei
    Shibata, Takanori
    ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (17) : 2850 - 2854
  • [28] One-Pot Synthesis of Quinazolinones via Iridium-Catalyzed Hydrogen Transfers
    Zhou, Jianguang
    Fang, Jie
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (19) : 7730 - 7736
  • [29] Iridium-Catalyzed Sequential sp3 C-H Alkylation of an N-Methyl Group with Alkenes Towards the Synthesis of α-Substituted Amines
    Hattori, Hiroshi
    Nishimura, Takahiro
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (24) : 4827 - 4831
  • [30] Iridium-Catalyzed C-Alkylation of Methyl Group on N-Heteroaromatic Compounds using Alcohols
    Onoda, Mitsuki
    Fujita, Ken-ichi
    ORGANIC LETTERS, 2020, 22 (18) : 7295 - 7299
12345