Efficient and selective hydrogenation of amides to alcohols and amines using a well-defined manganese–PNN pincer complex† †Electronic supplementary information (ESI) available: General experimental procedures, additional schemes and figures, characterization data and NMR spectra are available. See D
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Veronica Papa | Matthias Beller | Kathrin Junge | Elisabetta Alberico | M. Beller | H. Junge | E. Alberico | K. Junge | Henrik Junge | Jose R Cabrero-Antonino | Anke Spanneberg | J. R. Cabrero-Antonino | Veronica Papa | Anke Spanneberg
[1] Matthias Beller,et al. Catalytic Hydrogenation of Carboxylic Acid Esters, Amides, and Nitriles with Homogeneous Catalysts , 2014 .
[2] G. Georg,et al. Mild and selective hydrozirconation of amides to aldehydes using Cp2Zr(H)Cl: scope and mechanistic insight. , 2007, Journal of the American Chemical Society.
[3] W. Leitner,et al. Homogeneous catalytic hydrogenation of amides to amines. , 2013, Chemistry.
[4] P. Chirik. Iron- and Cobalt-Catalyzed Alkene Hydrogenation: Catalysis with Both Redox-Active and Strong Field Ligands. , 2015, Accounts of chemical research.
[5] A. Papworth,et al. Selective hydrogenation of amides using Rh/Mo catalysts , 2010 .
[6] L. Ackermann,et al. Manganese-Catalyzed C–H Activation , 2016 .
[7] B. Breit,et al. Catalytic hydrogenation of amides to amines under mild conditions. , 2013, Angewandte Chemie.
[8] B. Foxman,et al. High-spin manganese(II) complexes of an amido/bis(phosphine) PNP ligand. , 2010, Inorganic chemistry.
[9] T. Ikariya,et al. Synthesis, structures, and reactivities of iron, cobalt, and manganese complexes bearing a pincer ligand with two protic pyrazole arms , 2014 .
[10] M. Beller,et al. Hydrogenation of Esters to Alcohols Catalyzed by Defined Manganese Pincer Complexes. , 2016, Angewandte Chemie.
[11] A. Slawin,et al. On the Functional Group Tolerance of Ester Hydrogenation and Polyester Depolymerisation Catalysed by Ruthenium Complexes of Tridentate Aminophosphine Ligands. , 2015, Chemistry.
[12] Yehoshoa Ben‐David,et al. Unprecedented iron-catalyzed selective hydrogenation of activated amides to amines and alcohols. , 2016, Chemical communications.
[13] M. Sanford,et al. Iron-Catalyzed Hydrogenation of Amides to Alcohols and Amines , 2016 .
[14] R. Ludwig,et al. Selective Catalytic Hydrogenations of Nitriles, Ketones, and Aldehydes by Well-Defined Manganese Pincer Complexes. , 2016, Journal of the American Chemical Society.
[15] M. Beller,et al. Towards a general ruthenium-catalyzed hydrogenation of secondary and tertiary amides to amines† †Electronic supplementary information (ESI) available: General procedures, additional tables and schemes, characterisation data and NMR spectra of the isolated compounds are available. See DOI: 10.1039/c5 , 2016, Chemical science.
[16] J. Okuda,et al. Chemoselective Reduction of Tertiary Amides to Amines Catalyzed by Triphenylborane. , 2016, Angewandte Chemie.
[17] B. de Bruin,et al. Hydrogenation of carboxylic acids with a homogeneous cobalt catalyst , 2015, Science.
[18] R. Langer,et al. Selective Hydrogenation of Amides to Amines and Alcohols Catalyzed by Improved Iron Pincer Complexes , 2016 .
[19] T. Cantat,et al. Efficient metal-free hydrosilylation of tertiary, secondary and primary amides to amines. , 2014, Chemical communications.
[20] D. Spasyuk,et al. Chemoselective hydrogenation of carbonyl compounds and acceptorless dehydrogenative coupling of alcohols. , 2015, Journal of the American Chemical Society.
[21] L. Shimon,et al. System with potential dual modes of metal-ligand cooperation: highly catalytically active pyridine-based PNNH-Ru pincer complexes. , 2014, Chemistry.
[22] Yehoshoa Ben‐David,et al. Template Catalysis by Metal-Ligand Cooperation. C-C Bond Formation via Conjugate Addition of Non-activated Nitriles under Mild, Base-free Conditions Catalyzed by a Manganese Pincer Complex. , 2016, Journal of the American Chemical Society.
[23] D. Spasyuk,et al. From esters to alcohols and back with ruthenium and osmium catalysts. , 2012, Angewandte Chemie.
[24] H. Brown,et al. Improved Procedure for Borane-Dimethyl Sulfide Reduction of Primary Amides to Amines, , 1981 .
[25] M. Beller,et al. Hydrogenation of esters to alcohols with a well-defined iron complex. , 2014, Angewandte Chemie.
[26] A. Sadow,et al. Magnesium-Catalyzed Mild Reduction of Tertiary and Secondary Amides to Amines , 2015 .
[27] David Cantillo. Mechanistic Insights on the Ruthenium‐Catalyzed Hydrogenation of Amides – C–N vs. C–O Cleavage , 2011 .
[28] C. J. Elsevier,et al. The handbook of homogeneous hydrogenation , 2006 .
[29] U. Schatzschneider. PhotoCORMs: Light-triggered release of carbon monoxide from the coordination sphere of transition metal complexes for biological applications , 2011 .
[30] Shou‐Fei Zhu,et al. Deoxygenative Hydrogenation of Amides Catalyzed by a Well-Defined Iridium Pincer Complex , 2016 .
[31] S. Bergens,et al. A highly active catalyst for the hydrogenation of amides to alcohols and amines. , 2011, Angewandte Chemie.
[32] Matthias Beller,et al. Efficient and selective N-alkylation of amines with alcohols catalysed by manganese pincer complexes , 2016, Nature Communications.
[33] A. Guyer,et al. Über die katalytische Reduktion aliphatischer Carbonsäureamide , 1955 .
[34] M. Beller,et al. NNP-Type Pincer Imidazolylphosphine Ruthenium Complexes: Efficient Base-Free Hydrogenation of Aromatic and Aliphatic Nitriles under Mild Conditions. , 2016, Chemistry.
[35] C. Senanayake,et al. A Practical Procedure for Reduction of Primary, Secondary and Tertiary Amides to Amines , 2013 .
[36] L. Shimon,et al. Manganese-Catalyzed Environmentally Benign Dehydrogenative Coupling of Alcohols and Amines to Form Aldimines and H2: A Catalytic and Mechanistic Study. , 2016, Journal of the American Chemical Society.
[37] Thomas Dombray,et al. Cobalt Carbonyl-Based Catalyst for Hydrosilylation of Carboxamides , 2013 .
[38] R. Noyori,et al. Metal-ligand bifunctional catalysis: a nonclassical mechanism for asymmetric hydrogen transfer between alcohols and carbonyl compounds. , 2001, The Journal of organic chemistry.
[39] G. W. Wheland,et al. Advanced Organic Chemistry , 1951, Nature.
[40] K. Kirchner,et al. Modularly designed transition metal PNP and PCP pincer complexes based on aminophosphines: synthesis and catalytic applications. , 2008, Accounts of chemical research.
[41] R. Langer,et al. Probing the effect of heterocycle-bonding in PNX-type ruthenium pre-catalysts for reactions involving H2. , 2015, Dalton transactions.
[42] Evan R. Antoniuk,et al. Catalytic hydrogenation of functionalized amides under basic and neutral conditions , 2015 .
[43] W. Bartley,et al. Rhenium Catalysts. VII. Rhenium(VI) Oxide1 , 1963 .
[44] M. Beller,et al. Direct Ruthenium-Catalyzed Hydrogenation of Carboxylic Acids to Alcohols. , 2015, Angewandte Chemie.
[45] D. Milstein,et al. Metal-ligand cooperation by aromatization-dearomatization: a new paradigm in bond activation and "green" catalysis. , 2011, Accounts of chemical research.
[46] R. Morris. Exploiting metal-ligand bifunctional reactions in the design of iron asymmetric hydrogenation catalysts. , 2015, Accounts of chemical research.
[47] M. Beller,et al. Zinc-catalyzed chemoselective reduction of tertiary and secondary amides to amines. , 2011, Chemistry.
[48] A. Papworth,et al. Selective Hydrogenation of Amides using Ruthenium/ Molybdenum Catalysts , 2010 .
[49] M. Beller,et al. Selective Ruthenium-Catalyzed Reductive Alkoxylation and Amination of Cyclic Imides. , 2016, Angewandte Chemie.
[50] H. Adkins,et al. The Synthesis of Pyrrolidines, Piperidines and Hexahydroazepines1,2 , 1936 .
[51] S. Bergens,et al. Base-catalyzed bifunctional addition to amides and imides at low temperature. A new pathway for carbonyl hydrogenation. , 2013, Journal of the American Chemical Society.
[52] Shaolin Zhou,et al. Mild and Selective Cobalt-Catalyzed Chemodivergent Transfer Hydrogenation of Nitriles. , 2016, Angewandte Chemie.
[53] Pavel A. Dub,et al. Catalytic Reductive Transformations of Carboxylic and Carbonic Acid Derivatives Using Molecular Hydrogen , 2012 .
[54] A. F. Hill,et al. Organotransition Metal Chemistry , 2000 .
[55] L. Ackermann,et al. Manganese(I)-Catalyzed Substitutive C-H Allylation. , 2016, Angewandte Chemie.
[56] S. Schneider,et al. Cooperative Aliphatic PNP Amido Pincer Ligands – Versatile Building Blocks for Coordination Chemistry and Catalysis , 2012 .
[57] M. Brookhart,et al. Development and mechanistic investigation of a highly efficient iridium(V) silyl complex for the reduction of tertiary amides to amines. , 2012, Journal of the American Chemical Society.
[58] Adam S. Hock,et al. Discovery of highly selective alkyne semihydrogenation catalysts based on first-row transition-metallated porous organic polymers. , 2014, Angewandte Chemie.
[59] N. Lugan,et al. Hydrosilylation of Aldehydes and Ketones Catalyzed by Half‐Sandwich Manganese(I) N‐Heterocyclic Carbene Complexes , 2014 .
[60] D. Milstein,et al. Bond activation and catalysis by ruthenium pincer complexes. , 2014, Chemical reviews.
[61] Yehoshoa Ben‐David,et al. Efficient homogeneous catalytic hydrogenation of esters to alcohols. , 2006, Angewandte Chemie.
[62] D. Cole-Hamilton,et al. The synthesis of amines by the homogeneous hydrogenation of secondary and primary amides. , 2007, Chemical communications.
[63] P. Goodrich,et al. Catalytic hydrogenation of tertiary amides at low temperatures and pressures using bimetallic Pt/Re-based catalysts , 2011 .
[64] T. Fuchikami,et al. Hydrogenation of amides by the use of bimetallic catalysts consisting of group 8 to 10, and group 6 or 7 metals , 1996 .
[65] T. Ritter,et al. 1,4-Functionalization of 1,3-dienes with low-valent iron catalysts. , 2015, Accounts of chemical research.
[66] Y. Diskin‐Posner,et al. Cobalt-catalyzed hydrogenation of esters to alcohols: unexpected reactivity trend indicates ester enolate intermediacy. , 2015, Angewandte Chemie.
[67] K. Mashima,et al. Hydrogenation of amides catalyzed by a combined catalytic system of a Ru complex with a zinc salt. , 2014, Chemical communications.
[68] J. Boncella,et al. The synthesis of PNP-supported low-spin nitro manganese(I) carbonyl complexes , 2016 .
[69] A. Volkov,et al. Chemoselective reduction of carboxamides. , 2016, Chemical Society reviews.
[70] C. Hardacre,et al. The First Continuous Flow Hydrogenation of Amides to Amines , 2013 .
[71] R. Whyman,et al. Review of methods for the catalytic hydrogenation of carboxamides. , 2014, Chemical reviews.
[72] S. Saito,et al. Cationic mononuclear ruthenium carboxylates as catalyst prototypes for self-induced hydrogenation of carboxylic acids , 2015, Nature Communications.
[73] Kyle A. Grice,et al. Manganese catalysts with bulky bipyridine ligands for the electrocatalytic reduction of carbon dioxide: eliminating dimerization and altering catalysis. , 2014, Journal of the American Chemical Society.
[74] Xumu Zhang,et al. Direct Catalytic Hydrogenation of Simple Amides: A Highly Efficient Approach from Amides to Amines and Alcohols. , 2017, Chemistry.
[75] S. Chakraborty,et al. Nickel and iron pincer complexes as catalysts for the reduction of carbonyl compounds. , 2015, Accounts of chemical research.
[76] E. Singleton,et al. New diphosphine-substituted carbonyl complexes of manganese , 1972 .
[77] Qi‐Lin Zhou,et al. Boron Lewis Acid Promoted Ruthenium‐Catalyzed Hydrogenation of Amides: An Efficient Approach to Secondary Amines , 2016 .
[78] L. Shimon,et al. Direct hydrogenation of amides to alcohols and amines under mild conditions. , 2010, Journal of the American Chemical Society.
[79] T. Groy,et al. A highly active manganese precatalyst for the hydrosilylation of ketones and esters. , 2014, Journal of the American Chemical Society.
[80] T. Miura,et al. Catalytic hydrogenation of unactivated amides enabled by hydrogenation of catalyst precursor , 2013 .
[81] T. L. Brown,et al. Flash photolytic investigation of photoinduced carbon monoxide dissociation from dinuclear manganese carbonyl compounds , 1984 .
[82] K. K. Hii,et al. Sustainable catalysis : challenges and practices for the pharmaceutical and fine chemical industries , 2013 .
[83] M. Szostak,et al. Highly Chemoselective Reduction of Amides (Primary, Secondary, Tertiary) to Alcohols using SmI2/Amine/H2O under Mild Conditions , 2014, Journal of the American Chemical Society.
[84] Stephen P. Thomas,et al. Recent Advances of Manganese Catalysis for Organic Synthesis , 2016 .
[85] H. Knölker,et al. Iron catalysis in organic synthesis. , 2015, Chemical reviews.
[86] A. Papworth,et al. Selective hydrogenation of amides using bimetallic Ru/Re and Rh/Re catalysts , 2011 .
[87] D. Nocera,et al. Ligand reactivity in diarylamido/bis(phosphine) PNP complexes of Mn(CO)3 and Re(CO)3. , 2009, Inorganic chemistry.
[88] T. Dietel,et al. Highly Active and Selective Manganese C=O Bond Hydrogenation Catalysts: The Importance of the Multidentate Ligand, the Ancillary Ligands, and the Oxidation State. , 2016, Angewandte Chemie.
[89] J. March. Advanced organic chemistry , 2016 .
[90] M. Beller,et al. A convenient and general iron-catalyzed reduction of amides to amines. , 2009, Angewandte Chemie.
[91] R. Bullock. Abundant Metals Give Precious Hydrogenation Performance , 2013, Science.
[92] M. Beller,et al. Efficient Base-Free Hydrogenation of Amides to Alcohols and Amines Catalyzed by Well-Defined Pincer Imidazolyl–Ruthenium Complexes , 2016 .
[93] A. Charette,et al. Controlled and chemoselective reduction of secondary amides. , 2010, Journal of the American Chemical Society.
[94] W. C. Lineberger,et al. Laser photoelectron spectrometry of the negative ions of iron and iron carbonyls. Electron affinity determination for the series Fe(CO)n, n = 0,1,2,3,4 , 1979 .
[95] T. Zell,et al. Hydrogenation and dehydrogenation iron pincer catalysts capable of metal-ligand cooperation by aromatization/dearomatization. , 2015, Accounts of chemical research.
[96] T. Atack,et al. Manganese-Catalyzed Borylation of Unactivated Alkyl Chlorides. , 2016, Journal of the American Chemical Society.
[97] M. Brookhart,et al. Iridium-catalyzed reduction of secondary amides to secondary amines and imines by diethylsilane. , 2012, Journal of the American Chemical Society.
[98] Masato M. Ito,et al. Catalytic hydrogenation of carboxamides and esters by well-defined Cp*Ru complexes bearing a protic amine ligand. , 2011, Journal of the American Chemical Society.
[99] M. Beller,et al. Two iron catalysts are better than one: a general and convenient reduction of aromatic and aliphatic primary amides. , 2012, Angewandte Chemie.
[100] W. Leitner,et al. Highly versatile catalytic hydrogenation of carboxylic and carbonic acid derivatives using a Ru-triphos complex: molecular control over selectivity and substrate scope. , 2014, Journal of the American Chemical Society.
[101] H. Adkins,et al. The Selective Hydrogenation of Substituted Amides , 1938 .