Direct Reductive Amination of Carbonyl Compounds with H2 Using Heterogeneous Catalysts in Continuous Flow as an Alternative to N-Alkylation with Alkyl Halides

被引:44
作者
Laroche, Benjamin [1 ]
Ishitani, Haruro [2 ]
Kobayashi, Shu [1 ,2 ]
机构
[1] Univ Tokyo, Dept Chem, Sch Sci, Bunkyo Ku, Tokyo 1130033, Japan
[2] Univ Tokyo, Green & Sustainable Chem Cooperat Lab, Grad Sch Sci, Bunkyo Ku, Tokyo 1130033, Japan
基金
日本学术振兴会; 日本科学技术振兴机构;
关键词
flow chemistry; reductive amination; heterogeneous catalysis; C-N bond formation; flow fine synthesis; SECONDARY-AMINES; ALIPHATIC-KETONES; HYDROGENATION; ALDEHYDES; SULFUR; PT/C; REGENERATION; DIOXIDE;
D O I
10.1002/adsc.201801457
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A general continuous-flow procedure for direct reductive amination of secondary and primary amines with aromatic and aliphatic aldehydes as well as ketones is reported. The use of hydrogen gas and commercially available Pt/C as a heterogeneous catalyst is a key. In addition to exhibiting an excellent functional group tolerance, this method allows the fast formation of C-N bonds without production of any hazardous chemical waste. Applications to the synthesis of key intermediates toward active pharmaceutical ingredients (Donepezil and Arformoterol/Tamsulosin) are also described.
引用
收藏
页码:4699 / 4704
页数:6
相关论文
共 49 条
[11]  
Escandon L. S., 2008, J HAZARD MATER, V153, P1
[12]   Selectivity issues in the catalytic multiphase reduction of functionalized halogenated aromatics over Pd/C, Pt/C, and Raney-Ni [J].
Evdokimova, G ;
Zinovyev, S ;
Perosa, A ;
Tundo, P .
APPLIED CATALYSIS A-GENERAL, 2004, 271 (1-2) :129-136
[13]   Development of a Hydrogenative Reductive Amination for the Synthesis of Evacetrapib: Unexpected Benefits of Water [J].
Frederick, Michael O. ;
Frank, Scott A. ;
Vicenzi, Jeffrey T. ;
LeTourneau, Michael E. ;
Berglund, K. Derek ;
Edward, Adler W. ;
Alt, Charles A. .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2014, 18 (04) :546-551
[14]   Continuous Flow Organic Chemistry: Successes and Pitfalls at the Interface with Current Societal Challenges [J].
Gerardy, Romaric ;
Emmanuel, Noemie ;
Toupy, Thomas ;
Kassin, Victor-Emmanuel ;
Tshibalonza, Nelly Ntumba ;
Schmitz, Michael ;
Monbaliu, Jean-Christophe M. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (20-21) :2301-2351
[15]   SULFUR POISONING AND REGENERATION OF PALLADIUM-BASED CATALYSTS .2. INFLUENCE OF ADSORBED SULFUR ON DEACTIVATION OF CARBONACEOUS DEPOSITS [J].
HOYOS, LJ ;
PRIMET, M ;
PRALIAUD, H .
JOURNAL OF THE CHEMICAL SOCIETY-FARADAY TRANSACTIONS, 1992, 88 (22) :3367-3373
[16]   Direct Catalytic Asymmetric Reductive Amination of Aliphatic Ketones Utilizing Diphenylmethanamine as Coupling Partner [J].
Huang, Haizhou ;
Zhao, Yunfei ;
Yang, Yang ;
Zhou, Le ;
Chang, Mingxin .
ORGANIC LETTERS, 2017, 19 (08) :1942-1945
[17]   Carbon Dioxide-promoted Selective Reductive Amination of Aliphatic Ketones with Aniline and Hydrogen Using a Pt/C Catalyst [J].
Ichikawa, Shinichiro ;
Seki, Tsunetake ;
Ikariya, Takao .
CHEMISTRY LETTERS, 2012, 41 (12) :1628-1629
[18]   Enantioselective Organometallic Catalysis in Flow [J].
Ishitani, Haruro ;
Saito, Yuki ;
Kobayashi, Shu .
ORGANOMETALLIC FLOW CHEMISTRY, 2016, 57 :213-248
[19]   Flow "Fine" Synthesis: High Yielding and Selective Organic Synthesis by Flow Methods [J].
Kobayashi, Shu .
CHEMISTRY-AN ASIAN JOURNAL, 2016, 11 (04) :425-436
[20]   Powerful Continuous-Flow Hydrogenation by using Poly(dimethyl)silane-Supported Palladium Catalysts [J].
Kobayashi, Shu ;
Okumura, Mikiko ;
Akatsuka, Yuichi ;
Miyamura, Hiroyuki ;
Ueno, Masaharu ;
Oyamada, Hidekazu .
CHEMCATCHEM, 2015, 7 (24) :4025-4029