One-Pot Reductive N-Alkylation with Carbonyl Compounds To Give Tertiary Amines via Borane Reduction of Imines

被引:16
|
作者
Tokizane, Masashi [2 ]
Sato, Kaori [2 ]
Sakami, Yuki [2 ]
Imori, Yoichiro [2 ]
Matsuo, Chika [2 ]
Ohta, Tetsuo [1 ]
Ito, Yoshihiko [2 ]
机构
[1] Doshisha Univ, Fac Life & Med Sci, Dept Biomed Informat, Kyoto 6100394, Japan
[2] Doshisha Univ, Fac Engn, Dept Mol Sci & Technol, Kyoto 6100394, Japan
来源
SYNTHESIS-STUTTGART | 2010年 / 01期
关键词
reductive N-alkylation; borane reduction; imines; tertiary amines; one-pot reaction; SECONDARY-AMINES; AMINATION; ALDEHYDES; KETONES; COMPLEX; REAGENTS; PYRIDINE; SOLVENT;
D O I
10.1055/s-0029-1217076
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
One-pot synthesis of tertiary amines via borane-mediated reduction of imines and reductive N-alkylation with carbonyl compounds is described. This protocol's reducing agent is only borane in the reduction of imines, and additional reductant is not necessary in reductive N-alkylation step. When using more than two equivalents of aldehydes, reductive N-alkylation proceeded in good yield.
引用
收藏
页码:36 / 42
页数:7
相关论文
共 50 条
  • [21] A one-pot reductive amination of ketones to primary amines using borane-dimethyl sulfide complex
    Johansson, A
    Lindstedt, EL
    Olsson, T
    ACTA CHEMICA SCANDINAVICA, 1997, 51 (03): : 351 - 353
  • [22] One-Pot Reductive Mono-N-alkylation of Aromatic Nitro Compounds Using Nitriles as Alkylating Reagents
    Neogi, Subhasish
    Naskar, Dinabandhu
    SYNTHETIC COMMUNICATIONS, 2011, 41 (13) : 1901 - 1915
  • [23] One-Pot Synthesis of Symmetrical Tertiary and Secondary Amines from Carbonyl Compounds, Ammonium Carbonate and Carbon Monoxide as a Reductant
    Muratov, Karim
    Afanasyev, Oleg, I
    Kuchuk, Ekaterina
    Runikhina, Sofiya
    Chusov, Denis
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (38) : 6557 - 6560
  • [24] One-Pot Sequence for Reductive-Acetylation of Carbonyl Compounds with (N-Methylimidazole)(tetrahydroborato)zinc Complex
    Setamdideh, Davood
    Khezri, Behrooz
    ASIAN JOURNAL OF CHEMISTRY, 2010, 22 (07) : 5766 - 5772
  • [25] One-pot photo-reductive N-alkylation of aniline and nitroarene derivatives with primary alcohols over Au-TiO2
    Stibal, David
    Sa, Jacinto
    van Bokhoven, Jeroen A.
    CATALYSIS SCIENCE & TECHNOLOGY, 2013, 3 (01) : 94 - 98
  • [26] "One pot" synthesis of tertiary amines: Ru(II) catalyzed direct reductive N-benzylation of imines with benzyl bromide derivatives
    Li, Bin
    Yu, Jinghao
    Li, Caihua
    Li, Yibiao
    Luo, Jianli
    Shao, Yan
    TETRAHEDRON LETTERS, 2017, 58 (02) : 137 - 141
  • [27] One-pot synthesis of secondary or tertiary amines from alcohols and amines via alkoxyphosphonium salts
    Froyen, P
    Juvvik, P
    TETRAHEDRON LETTERS, 1995, 36 (52) : 9555 - 9558
  • [28] A facile, one-pot reductive alkylation of aromatic and heteroaromatic amines in aqueous micellar media: a chemoenzymatic approach
    Ganesh, Krithika
    Sambasivam, Ganesh
    Karthikeyan, S.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (20) : 4264 - 4268
  • [29] Reductive N-Alkylation of Nitro Compounds to N-Alkyl and N,N-Dialkyl Amines with Glycerol as the Hydrogen Source
    Cui, Xinjiang
    Deng, Youquan
    Shi, Feng
    ACS CATALYSIS, 2013, 3 (05): : 808 - 811
  • [30] The ruthenium-catalyzed reduction and reductive n-alkylation of secondary Amides with hydrosilanes: Practical synthesis of secondary and tertiary amines by judicious choice of hydrosilanes
    Hanada, Shiori
    Ishida, Toshiki
    Motoyama, Yukihiro
    Nagashima, Hideo
    JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (20): : 7551 - 7559