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
  • [1] 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
  • [2] One-pot stibine modified Co2(CO)8 catalyzed reductive N-alkylation of primary amides with carbonyl compounds
    Rubio-Perez, Laura
    Sharma, Pankaj
    Javier Perez-Flores, F.
    Velasco, Luis
    Luis Arias, J.
    Cabrera, Armando
    TETRAHEDRON, 2012, 68 (10) : 2342 - 2348
  • [3] Direct One-Pot Reductive N-Alkylation of Nitroarenes by using Alcohols with Supported Gold Catalysts
    Tang, Chun-Hong
    He, Lin
    Liu, Yong-Mei
    Cao, Yong
    He, He-Yong
    Fan, Kang-Nian
    CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (26) : 7172 - 7177
  • [4] One-pot reductive amination of carbonyl compounds and nitro compounds via Ir-catalyzed transfer hydrogenation
    Luo, Renshi
    Tong, Jinghui
    Ouyang, Lu
    Liu, Liang
    Liao, Jianhua
    RSC ADVANCES, 2023, 13 (42) : 29607 - 29612
  • [5] Anchored Palladium Complex-Generated Clusters on Zirconia: Efficiency in Reductive N-Alkylation of Amines with Carbonyl Compounds under Hydrogen Atmosphere
    Zhang, Zhenzhong
    Ikeda, Takuya
    Murayama, Haruno
    Honma, Tetsuo
    Tokunaga, Makoto
    Motoyama, Yukihiro
    CHEMISTRY-AN ASIAN JOURNAL, 2022, 17 (07)
  • [6] Selective Synthesis of Secondary and Tertiary Amines by Reductive N-Alkylation of Nitriles and N-Alkylation of Amines and Ammonium Formate Catalyzed by Ruthenium Complex
    Alshakova, Iryna D.
    Nikonov, Georgii, I
    CHEMCATCHEM, 2019, 11 (21) : 5370 - 5378
  • [7] Efficient and Clean Gold-Catalyzed One-Pot Selective N-Alkylation of Amines with Alcohols
    He, Lin
    Lou, Xia-Bing
    Ni, Ji
    Liu, Yong-Mei
    Cao, Yong
    He, He-Yong
    Fan, Kang-Nian
    CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (47) : 13965 - 13969
  • [8] One-pot N-alkylation of primary amines to secondary amines by gold clusters supported on porous coordination polymers
    Ishida, Tamao
    Kawakita, Noriko
    Akita, Tomoki
    Haruta, Masatake
    GOLD BULLETIN, 2009, 42 (04): : 267 - 274
  • [9] Direct Leuckart-type reductive amination of aldehydes and ketones: a facile one-pot protocol for the preparation of secondary and tertiary amines
    O'Connor, Danielle
    Lauria, Ashley
    Bondi, Steven P.
    Saba, Shahrokh
    TETRAHEDRON LETTERS, 2011, 52 (01) : 129 - 132
  • [10] 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