Domino Hydrogenation-Reductive Amination of Phenols, a Simple Process To Access Substituted Cyclohexylamines

被引:55
作者
Jumde, Varsha R. [1 ]
Petricci, Elena [1 ]
Petrucci, Chiara [2 ]
Santillo, Niccolo [1 ]
Taddei, Maurizio [1 ]
Vaccaro, Luigi [2 ]
机构
[1] Univ Siena, Dipartimento Biotecnol Chim & Farm, I-53100 Siena, Italy
[2] Univ Perugia, CEMIN Dipartimento Chim Biol & Biotecnol, Lab Green Synthet Organ Chem, I-06123 Perugia, Italy
关键词
MINIMIZED PROTOCOL; PRIMARY AMINES; HECK REACTION; N-ALKYLATION; FORMIC-ACID; DERIVATIVES; FLOW; CATALYST; DESIGN; PHASE;
D O I
10.1021/acs.orglett.5b01842
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Phenols can be efficiently reduced by sodium formate and Pd/C as the catalyst in water and in the presence of amines to give the corresponding cydohexylamines. This reaction works at rt for 12 h or at 60 degrees C under mictowave dielectric heating for 20 min. With the exception of aniline, primary, secondary amines, amino alcohols, and even amino acids can be used as nucleophiles. The reductive process is based on a sustainable hydrogen source and a catalyst that can be efficiently recovered and reused. The protocol was developed into a continuous-flow production of cyclohexyl-amines in gram scale achieving very efficient preliminary results (TON 32.7 and TOF 5.45 h(-1)).
引用
收藏
页码:3990 / 3993
页数:4
相关论文
共 60 条
  • [11] One-pot reductive mono-N-alkylation of aniline and nitroarene derivatives using aldehydes
    Byun, Eunyoung
    Hong, Bomi
    De Castro, Kathlia A.
    Lim, Minkyung
    Rhee, Hakjune
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (25) : 9815 - 9817
  • [12] Hydrodeoxygenation of Guaiacol over Carbon-Supported Metal Catalysts
    Chang, Jie
    Danuthai, Tanate
    Dewiyanti, Silvia
    Wang, Chuan
    Borgna, Armando
    [J]. CHEMCATCHEM, 2013, 5 (10) : 3041 - 3049
  • [13] Selective Hydrogenation of Phenol and Derivatives over Polymer-Functionalized Carbon-Nanofiber-Supported Palladium Using Sodium Formate as the Hydrogen Source
    Chen, Aibing
    Li, Yonglei
    Chen, Jinzhu
    Zhao, Guoying
    Ma, Longlong
    Yu, Yifeng
    [J]. CHEMPLUSCHEM, 2013, 78 (11): : 1370 - 1378
  • [14] Explorations of Substituted Urea Functionality for the Discovery of New Activators of the Heme-Regulated Inhibitor Kinase
    Chen, Ting
    Takrouri, Khuloud
    Hee-Hwang, Sung
    Rana, Sandeep
    Yefidoff-Freedman, Revital
    Halperin, Jose
    Natarajan, Amarnath
    Morisseau, Christophe
    Hammock, Bruce
    Chorev, Michael
    Aktas, Bertal H.
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2013, 56 (23) : 9457 - 9470
  • [15] Palladium-catalyzed reductive coupling of phenols with anilines and amines: efficient conversion of phenolic lignin model monomers and analogues to cyclohexylamines
    Chen, Zhengwang
    Zeng, Huiying
    Gong, Hang
    Wang, Haining
    Li, Chao-Jun
    [J]. CHEMICAL SCIENCE, 2015, 6 (07) : 4174 - 4178
  • [16] Selective reduction of phenol derivatives to cyclohexanones in water under microwave irradiation
    Cheng, Haiyang
    Liu, Ruixia
    Wang, Qiang
    Wu, Chaoyong
    Yu, Yancun
    Zhao, Fengyu
    [J]. NEW JOURNAL OF CHEMISTRY, 2012, 36 (04) : 1085 - 1090
  • [17] Pd/MgO: Catalyst characterization and phenol hydrogenation activity
    Claus, P
    Berndt, H
    Mohr, C
    Radnik, J
    Shin, EJ
    Keane, MA
    [J]. JOURNAL OF CATALYSIS, 2000, 192 (01) : 88 - 97
  • [18] Design and synthesis of N-alkyldeoxynojirimycin derivatives with improved metabolic stability as inhibitors of BVDV and Tacaribe virus
    Du, Yanming
    Ye, Hong
    Guo, Fang
    Wang, Lijuan
    Gill, Tina
    Khan, Noshena
    Cuconati, Andrea
    Guo, Ju-Tao
    Block, Timothy M.
    Chang, Jinhong
    Xu, Xiaodong
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (14) : 4258 - 4262
  • [19] EMERSON WS, 1947, ORG REACTIONS, V4, P174
  • [20] Continuous Reductions and Reductive Aminations Using Solid NaBH4
    Gilmore, Kerry
    Vukelic, Stella
    McQuade, D. Tyler
    Koksch, Beate
    Seeberger, Peter H.
    [J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2014, 18 (12) : 1771 - 1776