Page 7 of 8
Journal of the American Chemical Society
1
2
3
4
5
6
7
8
9
15 Christiansen, J. A. Method of producing methyl alcohol from alkyl
formates. U.S. Patent 1,302,011, 1919.
heterogeneous CeO
7503-7506.
2
-supported Ru catalyst. Chem. Commun. 2018, 54,
1
6 Tonner, S. P.; Trimm, D. L.; Wainwright, M. S.; Cant, N. W., The
base-catalysed carbonylation of higher alcohols. J. Mol. Cat. 1983, 18, 215-
22.
7 Balaraman, E.; Gunanathan, C.; Zhang, J.; Shimon, L. J. W.; Milstein,
D., Efficient hydrogenation of organic carbonates, carbamates and formates
indicates alternative routes to methanol based on CO and CO. Nat. Chem.
011, 3, 609.
8 Marchionna, M.; Basini, L.; Aragno, A.; Lami, M.; Ancillotti, F.
34 Garg, J. A.; Chakraborty, S.; Ben-David, Y.; Milstein, D. Unprece-
dented Iron-Catalyzed Selective Hydrogenation of Activated Amides to
Amines and Alcohols. Chem. Commun. 2016, 52, 5285−5288.
35 Schneck, F.; Assmann, M.; Balmer, M.; Harms, K.; Langer, R. Selec-
tive Hydrogenation of Amides to Amines and Alcohols Catalyzed by
Improved Iron Pincer Complexes. Organometallics 2016, 35, 1931−1943
36 Rezayee, N. M.; Samblanet, D. C.; Sanford, M. S. Iron-Catalyzed
Hydrogenation of Amides to Alcohols and Amines. ACS Catal. 2016, 6,
6377−6383
37 Jayarathne, U.; Zhang, Y.; Hazari, N.; Bernskoetter, W. H. Selective
Iron-Catalyzed Deaminative Hydrogenation of Amides. Organometallics
2017, 36, 409−416
38 Xie, Y.; Hu, P.; Bendikov, T.; Milstein, D., Heterogeneously cata-
lyzed selective hydrogenation of amides to alcohols and amines. Catal. Sci.
Technol. 2018, 8, 2784-2788.
39 Leischner, T.; Spannenberg, A.; Junge, K.; Beller, M., Molecular De-
fined Molybdenum–Pincer Complexes and Their Application in Catalytic
Hydrogenations. Organometallics 2018, 37, 4402-4408.
40 Papa, V.; Cabrero-Antonino, J. R.; Alberico, E.; Spanneberg, A.;
Junge, K.; Junge, H.; Beller, M., Efficient and selective hydrogenation of
amides to alcohols and amines using a well-defined manganese–PNN
pincer complex. Chem. Sci. 2017, 8, 3576-3585.
41 Werkmeister, S.; Junge, K.; Beller, M., Catalytic Hydrogenation of
Carboxylic Acid Esters, Amides, and Nitriles with Homogeneous Catalysts.
Org. Process Res. Dev. 2014, 18, 289-302.
2
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1
Mechanistic studies on the homogeneous nickel-catalyzed low temperature
methanol synthesis. J. Mol. Catal. 1992, 75, 147
1
9 Mahajan, D.; Krisdhasima, V.; Sproull, R. D. Kinetic modelling of
homogeneous methanol synthesis catalyzed by base-promoted nickel
complexes. Can. J. Chem. 2001, 79, 848
2
0 Chen, Y. Z.; Liao, B. J.; Chen, B. J. One-step synthesis of methanol
from CO/H at low temperature over ultrafine CuB catalysts. Appl. Catal.,
A 2002, 236, 121.
1 Li, B.; Jens, K.-J., Low-Temperature and Low-Pressure Methanol
2
2
Synthesis in the Liquid Phase Catalyzed by Copper Alkoxide Systems. Ind.
Eng. Chem. Res. 2014, 53, 1735-1740.
2
2 Li, B.; Jens, K. J. Liquid-Phase Low-Temperature and Low-Pressure
Methanol Synthesis Catalyzed by a Raney Copper-Alkoxide System. Top.
Catal. 2013, 56, 725
2
3 Li, W.; Wu, X.-F., A Practical and General Base-Catalyzed Carbonyl-
ation of Amines for the Synthesis of N-Formamides. Chem. Eur. J. 2015, 21,
14943-14948.
24 Balaraman, E.; Gnanaprakasam, B.; Shimon, L. J. W.; Milstein, D.,
Direct Hydrogenation of Amides to Alcohols and Amines under Mild
Conditions. J. Am. Chem. Soc. 2010, 132, 16756-16758.
42 Rezayee, N. M.; Huff, C. A.; Sanford, M. S., Tandem Amine and Ru-
thenium-Catalyzed Hydrogenation of CO
2015, 137, 1028-1031.
43 Everett, M.; Wass, D. F., Highly productive CO
methanol – a tandem catalytic approach via amide intermediates. Chem.
Commun. 2017, 53, 9502-9504.
44 Kothandaraman, J.; Goeppert, A.; Czaun, M.; Olah, G. A.; Prakash,
G. K. S., Conversion of CO from Air into Methanol Using a Polyamine
and a Homogeneous Ruthenium Catalyst. J. Am. Chem. Soc. 2016, 138,
2
to Methanol. J. Am. Chem. Soc.
2
5 Zhou, Y.; Khan, R.; Fan, B.; Xu, L., Ruthenium-Catalyzed Selective
2
hydrogenation to
Reduction of Carboxylic Esters and Carboxamides. Synthesis 2019, 51,
2
491-2505.
26 John, J. M.; Bergens, S. H., A Highly Active Catalyst for the Hydro-
genation of Amides to Alcohols and Amines. Angew. Chem., Int. Ed. 2011,
0, 10377-10380.
7 Kita, Y.; Higuchi, T.; Mashima, K., Hydrogenation of amides cata-
2
5
2
778-781.
4
5
lyzed by a combined catalytic system of a Ru complex with a zinc salt.
Chem. Commun. 2014, 50, 11211-11213.
Zhang, L.; Han, Z.; Zhao, X.; Wang, Z.; Ding, K., Highly Efficient Ru-
thenium-Catalyzed N-Formylation of Amines with H
Chem., Int. Ed. 2015, 54, 6186-6189.
2
and CO . Angew.
2
2
8 Cabrero-Antonino, J. R.; Alberico, E.; Drexler, H.-J.; Baumann, W.;
Junge, K.; Junge, H.; Beller, M., Efficient Base-Free Hydrogenation of
Amides to Alcohols and Amines Catalyzed by Well-Defined Pincer Imid-
azolyl–Ruthenium Complexes. ACS Catalysis 2016, 6, 47-54.
46 Kar, S.; Sen, R.; Kothandaraman, J.; Goeppert, A.; Chowdhury, R.;
Munoz, S. B.; Haiges, R.; Prakash, G. K. S., Mechanistic Insights into
Ruthenium-Pincer-Catalyzed Amine-Assisted Homogeneous Hydrogena-
tion of CO2 to Methanol. J. Am. Chem. Soc. 2019, 141, 3160-3170.
47 Dohm, S.; Hansen, A.; Steinmetz, M.; Grimme, S.; Checinski, M. P.,
Comprehensive Thermochemical Benchmark Set of Realistic Closed-Shell
Metal Organic Reactions. J. Chem. Theory Comput 2018, 14, 2596-2608.
48 Elangovan, S.; Topf, C.; Fischer, S.; Jiao, H.; Spannenberg, A.; Bau-
mann, W.; Ludwig, R.; Junge, K.; Beller, M., Selective Catalytic Hydrogena-
tions of Nitriles, Ketones, and Aldehydes by Well-Defined Manganese
Pincer Complexes. J. Am. Chem. Soc. 2016, 138, 8809-8814.
2
9 Miura, T.; Held, I. E.; Oishi, S.; Naruto, M.; Saito, S., Catalytic hy-
drogenation of unactivated amides enabled by hydrogenation of catalyst
precursor. Tet. Lett. 2013, 54, 2674-2678.
30 Shi, L.; Tan, X.; Long, J.; Xiong, X.; Yang, S.; Xue, P.; Lv, H.; Zhang,
X., Direct Catalytic Hydrogenation of Simple Amides: A Highly Efficient
Approach from Amides to Amines and Alcohols. Chem. Eur. J. 2017, 23,
5
46-548.
1 Miura, T.; Naruto, M.; Toda, K.; Shimomura, T.; Saito, S., Multifac-
3
eted catalytic hydrogenation of amides via diverse activation of a sterically
confined bipyridine–ruthenium framework. Sci. Rep. 2017, 7, 1586.
32 Wang, Z.; Li, Y.; Liu, Q.-b.; Solan, G. A.; Ma, Y.; Sun, W.-H., Direct
Hydrogenation of a Broad Range of Amides under Base-free Conditions
using an Efficient and Selective Ruthenium(II) Pincer Catalyst. Chem-
CatChem 2017, 9, 4275-4281.
49 Kar, S.; Goeppert, A.; Kothandaraman, J.; Prakash, G. K. S., Manga-
nese-Catalyzed Sequential Hydrogenation of CO to Methanol via
2
Formamide. ACS Catalysis 2017, 7, 6347-6351.
5
0
Bruneau-Voisine, A.; Wang, D.; Roisnel, T.; Darcel, C.; Sortais, J.-B.,
Hydrogenation of ketones with a manganese PN3P pincer pre-catalyst.
Catal. Commun. 2017, 92, 1-4.
3
3 Tamura, M.; Ishikawa, S.; Betchaku, M.; Nakagawa, Y.; Tomishige,
K., Selective hydrogenation of amides to alcohols in water solvent over a
7
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