Ir(bis-NHC)-Catalyzed Direct Conversion of Amines to Alcohols in Aqueous Glycerol

被引:4
作者
Cheong, Yeon-Joo [1 ]
Lee, Seunghyeon [1 ]
Hwang, Sang Joon [1 ]
Yoon, Woojin [1 ]
Yun, Hoseop [1 ]
Jang, Hye-Young [1 ]
机构
[1] Ajou Univ, Dept Energy Syst Res, Suwon 16499, South Korea
关键词
Iridium; Dehydrogenation; Amines; Alcohols; Glycerol; TRANSFER HYDROGENATION; TRANSITION-METAL; N-ALKYLATION; IRIDIUM; REDUCTION; COMPLEXES; DEHYDROGENATION; ALDEHYDES; CATALYSTS; SOLVENT;
D O I
10.1002/ejoc.201900042
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Sustainable catalytic conversion of amines to alcohols was realized in the presence of iridium catalysts and aqueous glycerol. Iridium catalysts involving bis-N-heterocyclic carbene (bis-NHC) show good reactivity and stability in the conversion of amines into alcohols in aqueous glycerol. The reaction was initiated with the dehydrogenation of amines and followed by hydrolysis and reduction. Iridium catalysts play dual roles in both the dehydrogenation and reduction steps. By employing glycerol as a solvent and hydrogen source, the final reduction was facilitated. The synthesis and characterization of various Ir(bis-NHC) complexes are described along with the catalytic reaction results of the amine into alcohol conversion.
引用
收藏
页码:1940 / 1943
页数:4
相关论文
共 38 条
[1]   Chelated iridium(III) bis-carbene complexes as air-stable catalysts for transfer hydrogenation [J].
Albrecht, M ;
Miecznikowski, JR ;
Samuel, A ;
Faller, JW ;
Crabtree, RH .
ORGANOMETALLICS, 2002, 21 (17) :3596-3604
[2]  
[Anonymous], 2007, ANGEW CHEM, V119, P4516
[3]  
[Anonymous], 2010, ANGEW CHEM, V122, P1510
[4]   Transfer Hydrogenation from Glycerol: Activity and Recyclability of Iridium and Ruthenium Sulfonate-Functionalized N-Heterocyclic Carbene Catalysts [J].
Azua, Arturo ;
Finn, Matthew ;
Yi, Hannah ;
Dantas, Ana Beatriz ;
Voutchkova-Kostal, Adelina .
ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2017, 5 (05) :3963-3972
[5]   Iridium NHC Based Catalysts for Transfer Hydrogenation Processes Using Glycerol as Solvent and Hydrogen Donor [J].
Azua, Arturo ;
Mata, Jose A. ;
Peris, Eduardo .
ORGANOMETALLICS, 2011, 30 (20) :5532-5536
[6]   Water-Soluble IrIII N-Heterocyclic Carbene Based Catalysts for the Reduction of CO2 to Formate by Transfer Hydrogenation and the Deuteration of Aryl Amines in Water [J].
Azua, Arturo ;
Sanz, Sergio ;
Peris, Eduardo .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (14) :3963-3967
[7]   The Catalytic Amination of Alcohols [J].
Baehn, Sebastian ;
Imm, Sebastian ;
Neubert, Lorenz ;
Zhang, Min ;
Neumann, Helfried ;
Beller, Matthias .
CHEMCATCHEM, 2011, 3 (12) :1853-1864
[8]   Improved utilisation of renewable resources: New important derivatives of glycerol [J].
Behr, Arno ;
Eilting, Jens ;
Irawadi, Ken ;
Leschinski, Julia ;
Lindner, Falk .
GREEN CHEMISTRY, 2008, 10 (01) :13-30
[9]   In situ oxidation-imine formation-reduction routes from alcohols to amines [J].
Blackburn, L ;
Taylor, RJK .
ORGANIC LETTERS, 2001, 3 (11) :1637-1639
[10]   CATALYTIC TRANSFER HYDROGENATION [J].
BRIEGER, G ;
NESTRICK, TJ .
CHEMICAL REVIEWS, 1974, 74 (05) :567-580