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
  • [41] Synthesis of N-phenyl β-amino acids via iridium-catalyzed asymmetric hydrogenation using mixed monodentate ligands
    Mrsic, Natasa
    Panella, Lavinia
    Minnaard, Adriaan J.
    Feringa, Ben L.
    de Vries, Johannes G.
    TETRAHEDRON-ASYMMETRY, 2011, 22 (01) : 36 - 39
  • [42] Iridium-Catalyzed Branch-Selective and Enantioselective C2-Alkylation of N-Benzimidazolyl Indoles
    Yamakawa, Kentaro
    Nishimura, Takahiro
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (12) : 2013 - 2017
  • [43] Iridium-Catalyzed Asymmetric Ring-Opening Reactions of N-Boc-azabenzonorbornadiene with Secondary Amine Nucleophiles
    Yang, Dingqiao
    Long, Yuhua
    Wang, Huan
    Zhang, Zhenming
    ORGANIC LETTERS, 2008, 10 (21) : 4723 - 4726
  • [44] Palladium catalyzed alkylation of indole via aliphatic C-H bond activation of tertiary amine
    Ramachandiran, K.
    Muralidharan, D.
    Perumal, P. T.
    TETRAHEDRON LETTERS, 2011, 52 (28) : 3579 - 3583
  • [45] Unified synthesis of mono/bis-arylated phenols via RhIII-catalyzed dehydrogenative coupling
    Wu, Qian
    Chen, Ying
    Yan, Dingyuan
    Zhang, Muyue
    Lu, Yi
    Sun, Wei-Yin
    Zhao, Jing
    CHEMICAL SCIENCE, 2017, 8 (01) : 169 - 173
  • [46] 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)
  • [47] Studies toward the mechanism of amine-directed, iridium-catalyzed C-H borylation of N,N-dimethylbenzylamines
    Oliver, Clay
    McGarry, Kathryn
    Clark, Timothy
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 251
  • [48] Stereoselective synthesis of silyl enol ethers via the iridium-catalyzed isomerization of allyl silyl ethers
    Ohmura, T
    Yamamoto, Y
    Miyaura, N
    ORGANOMETALLICS, 1999, 18 (03) : 413 - 416
  • [49] Effective Recognition of Different Types of Amino Groups: From Aminobenzenesulfonamides to Amino-(N-alkyl)benzenesulfonamides via Iridium-Catalyzed N-Alkylation with Alcohols
    Lu, Lei
    Ma, Juan
    Qu, Panpan
    Li, Feng
    ORGANIC LETTERS, 2015, 17 (10) : 2350 - 2353
  • [50] 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
12345