SNS-Ligands for Ru-Catalyzed Homogeneous Hydrogenation and Dehydrogenation Reactions

被引:27
作者
Schoergenhumer, Johannes [1 ]
Zimmermann, Axel [2 ]
Waser, Mario [1 ]
机构
[1] Johannes Kepler Univ Linz, Inst Organ Chem, Altenbergerstr 69, A-4040 Linz, Austria
[2] Patheon Austria, Part Thermo Fisher Sci, St Peterstr 25, A-4020 Linz, Austria
关键词
RUTHENIUM PINCER COMPLEXES; CARBOXYLIC-ACID ESTERS; ASYMMETRIC HYDROGENATION; NNS-COMPLEXES; ALCOHOLS; EFFICIENT; REDUCTION; KETONES; SULFUR; NICKEL;
D O I
10.1021/acs.oprd.8b00142
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A detailed study of literature-known and novel S-containing pincer-type ligands for ruthenium-catalyzed homogeneous hydrogenation and dehydrogenation reactions was carried out. The scope and limitations of these catalysts were carefully investigated, and it was shown that simple bench-stable SNS-Ru complexes can be used to facilitate the hydrogenation of a variety of different substrates at a maximum H-2 pressure of 20 bar under operationally simple, easy to scale up, glovebox-free conditions by using starting materials and reagents that do not require any special purification prior to use. It was also shown that such complexes can be used to catalyze the dehydrogenative coupling of alcohols and amines to get amides as well as for the dehydrogenative dimerization of alcohols to esters.
引用
收藏
页码:862 / 870
页数:9
相关论文
共 50 条
[1]   Asymmetric homogeneous hydrogenations at scale [J].
Ager, David J. ;
de Vries, Andre H. M. ;
de Vries, Johannes G. .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (08) :3340-3380
[2]  
[Anonymous], 2007, The Handbook of Homogeneous Hydrogenation
[3]   Development of Chiral Spiro P-N-S Ligands for Iridium-Catalyzed Asymmetric Hydrogenation of -Alkyl--Ketoesters [J].
Bao, Deng-Hui ;
Wu, Hui-Ling ;
Liu, Chao-Lun ;
Xie, Jian-Hua ;
Zhou, Qi-Lin .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (30) :8791-8794
[4]   Recent developments of iron pincer complexes for catalytic applications [J].
Bauer, Gerald ;
Hu, Xile .
INORGANIC CHEMISTRY FRONTIERS, 2016, 3 (06) :741-765
[5]   Modularly designed transition metal PNP and PCP pincer complexes based on aminophosphines: Synthesis and catalytic applications [J].
Benito-Garagorri, David ;
Kirchner, Karl .
ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (02) :201-213
[6]   Nickel and Iron Pincer Complexes as Catalysts for the Reduction of Carbonyl Compounds [J].
Chakraborty, Sumit ;
Bhattacharya, Papri ;
Dai, Huiguang ;
Guan, Hairong .
ACCOUNTS OF CHEMICAL RESEARCH, 2015, 48 (07) :1995-2003
[7]  
Chase P.A., 2015, TOP ORGANOMETAL CHEM, V54, P1
[8]   Unexpected Direct Hydride Transfer Mechanism for the Hydrogenation of Ethyl Acetate to Ethanol Catalyzed by SNS Pincer Ruthenium Complexes [J].
Chen, Xiangyang ;
Jing, Yuanyuan ;
Yang, Xinzheng .
CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (06) :1950-1957
[9]   Synthesis and characterization of oxorhenium(V)-'3+1' mixed thiolate [SNS]/[S] and [ONS]/[S] complexes.: Crystal and molecular structures of [ReO(η 3-SCH2C5H3NCH2S)(η1-C6H4Br-4-S)], [ReO(η3-SCH2C5H3NCH2O)(η1-C6H4X-4-S)] (X = Cl, OMe), [ReO(η3-SCH2C5H3NCH2O)(η1-C6H4OCH3-4-CH2S)] and [ReO(η3-SCH2C5H3NCH2S)(η1-C5H4NH-2-S)][Cl] [J].
Chen, XY ;
Femia, FJ ;
Babich, JW ;
Zubieta, J .
INORGANICA CHIMICA ACTA, 2000, 307 (1-2) :88-96
[10]   Recent developments in the homogeneous hydrogenation of carboxylic acid esters [J].
Clarke, Matthew L. .
CATALYSIS SCIENCE & TECHNOLOGY, 2012, 2 (12) :2418-2423