Ruthenium-catalyzed amide-bond formation

Topics in Organometallic Chemistry

Volumn 48, Issue , 2014, Pages 81-118

  Crochet, Pascale ^a   Cadierno, Victorio ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

Amide bond formation; Dehydrogenative amidation; Hydrolytic amidation; Nitrile hydration; Rearrangements; Ruthenium catalysts

Indexed keywords

EID: 84913589461     PISSN: 14366002     EISSN: 16168534     Source Type: Book Series    
DOI: 10.1007/3418_2014_78     Document Type: Article

References (145)

1. Zabicky J (1970) The chemistry of amides. Wiley, New York
2. Greenberg A, Breneman CM, Liebman (2000) The amide linkage: structural significance in chemistry, Biochemistry and materials science. Wiley, New York
3. Dugger RW, Ragan JA, Ripin DHB (2005) Survey of GMP bulk reactions run in a research facility between 1985 and 2002. Org Process Res Dev 9:253
4. Carey JS, Laffan D, Thomson C, Williams TM (2006) Analysis of the reactions used for the preparation of drug candidate molecules. Org Biomol Chem 4:2337
5. Ghose AK, Viswanadhan VN, Wendoloski JJ (1999) A knowledge-based approach in designing combinatorial or medicinal chemistry libraries for drug discovery. 1. A qualitative and quantitative characterization of known drug databases. J Comb Chem 1:55
6. Montalbetti CAGN, Falque V (2005) Amide bond formation and peptide coupling. Tetrahedron 61:10827
7. Valeur E, Bradley M (2009) Amide bond formation: beyond the myth of coupling reagents. Chem Soc Rev 38:606
8. Constable DJC, Dunn PJ, Hayler JD, Humphrey GR, Leazer JL, Linderman RJ, Lorenz K, Manley J, Pearlman BA, Wells A, Zaks A, Zhang TY (2007) Key green chemistry research areas - a perspective from pharmaceutical manufacturers. Green Chem 9:411
9. Allen CL, Williams JMJ (2011) Metal-catalysed approaches to amide bond formation. Chem Soc Rev 40:3405
10. Pattabiraman VR, Bode JW (2011) Rethinking amide bond synthesis. Nature 480:471
11. Roy S, Roy S, Gribble GW (2012) Metal-catalyzed amidation. Tetrahedron 68:9867
12. García-Alvarez R, Crochet P, Cadierno V (2013) Metal-catalyzed amide bond forming reactions in an environmentally friendly aqueous medium: Nitrile hydrations and beyond. Green Chem 15:46
13. Bode JW (2013) Reinventing amide bond formation. Top Organomet Chem 44:13
14. Singh C, Kumar V, Sharma U, Kumar N, Singh B (2013) Emerging catalytic methods for amide synthesis. Curr Org Synth 10:241
15. Yamada H, Kobayashi M (1996) Nitrile hydratase and its application to industrial production of acrylamide. Biosci Biotech Biochem 60:1391
16. Tao J, Xu JH (2009) Biocatalysis in development of green pharmaceutical processes. Curr Opin Chem Biol 13:45
17. Sanchez S, Demain AL (2011) Enzymes and bioconversions of industrial, pharmaceutical, and biotechnological significance. Org Process Res Dev 15:224
18. Li B, Su J, Tao J (2011) Enzyme and process development for production of nicotinamide. Org Process Res Dev 15:291
19. Kopylovich MN, Kukushkin VY, Haukka M, Frausto da Silva JJR, Pombeiro AJL (2002) Zinc(II)/ketoxime system as a simple and efficient catalyst for hydrolysis of organonitriles. Inorg Chem 41:4789
20. Kukushkin VY, Pombeiro AJL (2002) Additions to metal-activated organonitriles. Chem Rev 102:1771
21. Kukushkin VY, Pombeiro AJL (2005) Metal-mediated and metal-catalyzed hydrolysis of nitriles. Inorg Chim Acta 358:1
22. Ahmed TJ, Knapp SMM, Tyler DR (2011) Frontiers in catalytic nitrile hydration: nitrile and cyanohydrin hydration catalyzed by homogeneous organometallic complexes. Coord Chem Rev 255:949
23. Murahashi SI, Sasao S, Saito E, Naota T (1992) Ruthenium-catalyzed hydration of nitriles and transformation of 5-keto nitriles to ene-lactams. J Org Chem 57:2521
24. Murahashi SI, Sasao S, Saito E, Naota T (1993) Ruthenium-catalyzed hydration of nitriles and transformation of 5-keto nitriles to ene-lactams: Total synthesis of (—)-pumiliotoxin C. Tetrahedron 49:8805
25. Murahashi SI, Naota T (1996) A new way for efficient catalysis by using low valent ruthenium complexes as redox Lewis acid and base catalysts. Bull Chem Soc Jpn 69:1805
26. Murahashi SI, Takaya H (2000) Low-valent ruthenium and iridium hydride complexes as alternatives to Lewis acid and base catalysts. Acc Chem Res 33:225
27. Fung WK, Huang X, Man ML, Ng SM, Hung MY, Lin Z, Lau CP (2003) Dihydrogen-bond-promoted catalysis: Catalytic hydration of nitriles with the indenylruthenium hydride complex (r|5-C9H7)Ru(dppm)H (dppm = bis(diphenylphosphino)methane). J Am Chem Soc 125:11539
28. Leung CW, Zheng W, Wang D, Ng SM, Yeung CH, Zhou Z, Lin Z, Lau CP (2007) Catalytic H/D exchange between organic compounds and D2O with TpRu(PPh3)(CH3CN)H (Tp ¼ hydro(trispyrazolyl)borate). Reaction of TpRu(PPh3)(CH3CN)H with water to form acetamido complex TpRu(PPh3)(H2O)(NHC(O)CH3). Organometallics 26:1924
29. Leung CW, Zheng W, Zhou Z, Lin Z, Lau CP (2008) Mechanism of catalytic hydration of nitriles with hydrotris(pyrazolyl)borato (Tp) ruthenium complexes. Organometallics 27:4957
30. Li T, Bergner I, Haque FN, Zimmer-De Iuliis M, Song D, Morris RH (2007) Hydrogenation of benzonitrile to benzylamine catalyzed by ruthenium hydride complexes with P-NH-NH-P tetradentate ligands: evidence for a hydridic-protonic outer sphere mechanism. Organome-tallics 26:5940
31. Yi CS, Zeczycki TN, Lindeman SV (2008) Kinetic, spectroscopic, and X-ray crystallographic evidence for the cooperative mechanism of the hydration of nitriles catalyzed by a tetranuclear ruthenium-μ-oxo-μ-hydroxo complex. Organometallics 27:2030
32. Utsunomiya M, Takahashi K, Oshiki T, Takai K (2004) New ruthenium complex, method for producing the same and method for producing amide compound using the same. Jpn Kokai Tokkyo Koho JP 2004, 269522
33. Oshiki T, Yamashita H, Sawada K, Utsunomiya M, Takahashi K, Takai K (2005) Dramatic rate acceleration by a diphenyl-2-pyridylphosphine ligand in the hydration of nitriles catalyzed by Ru(acac)2 complexes. Organometallics 24:6287
34. Oshiki T, Hyodo I, Ishizuka A (2005) Highly reactive bifunctional chemical catalysts for the hydration of nitriles. J Synth Org Chem Jpn 68:41
35. Oshiki T, Takai K (2008) Method for producing amide compound and catalyst used for the same method. Jpn Kokai Tokkyo Koho JP 2008, 088153
36. Muranaka M, Hyodo I, Okumura W, Oshiki T (2011) 2-Diphenylphosphanyl-4-pyridyl (dimethyl)amine as an effective ligand for the ruthenium(II) complex catalyzed homogeneous hydration of nitriles under neutral conditions. Catal Today 164:552
37. Smejkal T, Breit B (2007) Self-assembled bidentate ligands for ruthenium-catalyzed hydra- tion of nitriles. Organometallics 26:2461
38. García-Alvarez R, García-Garrido, SE, Díez J, Crochet P, Cadierno V (2012) Arene-ruthenium (II) and bis(allyl)-ruthenium(IV) complexes containing 2-(diphenylphosphanyl)pyridine ligands: Potential catalysts for nitrile hydration reactions? Eur J Inorg Chem 4218
39. García-Alvarez R, Díez J, Crochet P, Cadierno V (2010) Arene-ruthenium(II) complexes containing amino-phosphine ligands as catalysts for nitrile hydration reactions. Organome-tallics 29:3955
40. Cadierno V, Francos J, Gimeno J (2008) Selective ruthenium-catalyzed hydration of nitriles to amides in pure aqueous medium under neutral conditions. Chem Eur J 14:6601
41. Cadierno V, Díez J, Francos J, Gimeno J (2010) Bis(allyl)ruthenium(IV) complexes containing water-soluble phosphane ligands: Synthesis, structure, and application as catalysts in the selective hydration of organonitriles into amides. Chem Eur J 16:9808
42. Lee WC, Frost BJ (2012) Aqueous and biphasic nitrile hydration catalyzed by a recyclable Ru(II) complex under atmospheric conditions. Green Chem 14:62
43. Frost BJ, Lee WC (2013) Nitrile hydration catalyzed by recyclable ruthenium complexes. US Pat Appl US2013/0,096,344
44. Lee WC, Sears JM, Enow RA, Eads K, Krogstad DA, Frost BJ (2013) Hemilabile β-aminophosphine ligands derived from 1,3,5-triaza-7-phosphaadamantane: Application in aqueous ruthenium catalyzed nitrile hydration. Inorg Chem 52:1737
45. García-Alvarez R, Zablocka M, Crochet P, Duhayon C, Majoral JP, Cadierno V (2013) Thiazolyl-phosphine hydrochloride salts: effective auxiliary ligands for ruthenium-catalyzed nitrile hydration reactions and related amide bond forming processes in water. Green Chem 15:2447
46. García-Alvarez R, Francos J, Crochet P, Cadierno V (2011) Ibuprofenamide: A convenient method of synthesis by catalytic hydration of 2-(4-isobutylphenyl)propionitrile in pure aqueous medium. Tetrahedron Lett 52:4218
47. García-Alvarez R, Díez J, Crochet P, Cadierno V (2011) Arene-ruthenium(II) complexes containing inexpensive tris(dimethylamino)phosphine: Highly efficient catalysts for the selective hydration of nitriles to amides. Organometallics 30:5442
48. Knapp SMM, Sherbow TJ, Juliette JJ, Tyler DR (2012) Cyanohydrin hydration with [Ru(η6-p-cymene)Cl2PR3] complexes. Organometallics 31:2941
49. Knapp SMM, Sherbow TJ, Yelle RB, Zakharov LN, Juliette JJ, Tyler DR (2013) Mechanistic investigations and secondary coordination sphere effects in the hydration of nitriles with [Ru(η6-arene)Cl2PR3] complexes. Organometallics 32:824
50. Knapp SMM, Sherbow TJ, Yelle RB, Juliette JJ, Tyler DR (2013) Catalytic nitrile hydration with [Ru(η6-p-cymene)Cl2(PR2R´)] complexes: Secondary coordination sphere effects with phosphine oxide and phosphinite ligands. Organometallics 32:3744
51. Oshiki T, Muranaka M (2012) Metal complex compound and amide production method that utilizes said metal complex compound. PCT Int Appl WO2012/017966
52. Ashraf SM, Berger I, Nazarov AA, Hartinger CG, Koroteev MP, Nifantev EE, Keppler BK (2008) Phosphite-derivatized ruthenium-carbohydrate complexes in the catalytic hydration of nitriles. Chem Biodiversity 5:1640
53. Ashraf SM, Kandioller W, Mendoza-Ferri MG, Nazarov AA, Hartinger CG, Keppler BK (2008) The hydration of chloroacetonitriles catalyzed by mono- and dinuclear RuII- and OsII-arene complexes. Chem Biodiversity 5:2060
54. Martín M, Horváth H, Sola E, Kathó A, Joó F (2009) Water-soluble triisopropylphosphine complexes of ruthenium(II): synthesis, equilibria, and acetonitrile hydration. Organometal-lics 28:561
55. Cavarzan A, Scarso A, Strukul G (2010) Efficient nitrile hydration mediated by RuII catalysts in micellar media. Green Chem 12:790
56. Ferrer I, Rich J, Fontrodona X, Rodríguez M, Romero I (2013) Ru(II) complexes containing dmso and pyrazolyl ligands as catalysts for nitrile hydration in environmentally friendly media. Dalton Trans 42:13461
57. Kumar D, Masitas CA, Nguyen TN, Grapperhaus GA (2013) Bioinspired catalytic nitrile hydration by dithiolato, sulfinato/thiolato, and sulfenato/sulfinato ruthenium complexes. Chem Commun 49:294
58. Ammar HB, Miao X, Fischmeister C, Toupet L, Dixneuf PH (2010) Bidentate oxazoline-imine ruthenium(II) complexes: Intermediates in the methanolysis/hydration of nitrile groups. Organometallics 29:4234
59. Kamezaki S, Akiyama S, Kayaki Y, Kuwata S, Ikariya T (2010) Asymmetric nitrile-hydration with bifunctional ruthenium catalysts bearing chiral N-sulfonyldiamine ligands. Tetrahedron Asymmetry 21:1169
60. Yamaguchi K, Matsushita M, Mizuno N (2004) Efficient hydration of nitriles to amides in water, catalyzed by ruthenium hydroxide supported on alumina. Angew Chem Int Ed 43:1576
61. Polshettiwar V, Varma RS (2009) Nanoparticle-supported and magnetically recoverable ruthenium hydroxide catalyst: Efficient hydration of nitriles to amides in aqueous medium. Chem Eur J 15:1582
62. Baig RBN, Varma RS (2013) Organic synthesis via magnetic attraction: Benign and sustainable protocols using magnetic nanoferrites. Green Chem 15:398
63. Baig RBN, Varma RS (2012) A facile one-pot synthesis of ruthenium hydroxide nanoparticles on magnetic silica: Aqueous hydration of nitriles to amides. Chem Commun 48:6220
64. García-Garrido SE, Francos J, Cadierno V, Basset JM, Polshettiwar V (2011) Chemistry by nanocatalysis: First example of a solid-supported RAPTA complex for organic reactions in aqueous medium. ChemSusChem 4:104
65. Mori K, Yamaguchi K, Mizugaki T, Ebitani K, Kaneda K (2001) Catalysis of a hydroxyapatite-bound Ru complex: efficient heterogeneous oxidation of primary amines to nitriles in the presence of molecular oxygen. Chem Commun 461
66. Prakash GKS, Munoz SB, Papp A, Masood K, Bychinskaya I, Mathew T, Olah GA (2012) Nafion-Ru: A sustainable catalyst for selective hydration of nitriles to amides. Asian J Org Chem 1:146
67. Kurata T, Tamaru A, Murata Y, Nagashima S, Okano T, Ohfucchi K (1973) Unsaturated amides. Jpn Kokai Tokkyo Koho JP 48054021
68. Mizuno T (2005) Method for producing amide compounds by hydration reaction of nitrile compounds. Jpn Kokai Tokkyo Koho JP 2005170821
69. Oshiki T, Ishizuka A (2009) Method for producing amide compound and catalyst to be used therein. Jpn Kokai Tokkyo Koho JP 2009214099
70. Kumar S, Das P (2013) Solid-supported ruthenium(0): An efficient heterogeneous catalyst for hydration of nitriles to amides under microwave irradiation. New J Chem 37:2987
71. Cobley CJ, van den Heuvel M, Abbadi A, de Vries JG (2000) Platinum catalysed hydrolytic amidation of unactivated nitriles. Tetrahedron Lett 41:2467
72. van Dijk AJM, Duchateau R, Hensen EJM, Meuldijk J, Koning CE (2007) Polyamide synthesis from 6-aminocapronitrile, part 2: Heterogeneously catalyzed nitrile hydrolysis with consecutive amine amidation. Chem Eur J 13:7673
73. Allen CL, Lapkin AA, Williams JMJ (2009) An iron-catalysed synthesis of amides from nitriles and amines. Tetrahedron Lett 50:4262
74. Tamura M, Tonomura T, Shimizu KI, Satsuma A (2012) CeO2-catalyzed one-pot selective synthesis of N-alkyl amides from nitriles, amines and water. Appl Catal A Gen 417–418:6
75. Davulcu S, Allen CL, Milne K, Williams JMJ (2013) Catalytic conversion of nitriles into secondary- and tertiary amides. ChemCatChem 5:435
76. Li X, Li Z, Deng H, Zhou X (2013) An efficient protocol for the preparation of amides by copper-catalyzed reactions between nitriles and amines in water. Tetrahedron Lett 54:2212
77. Ghodsinia SSE, Akhlaghinia B, Safaei E, Eshghi H (2013) Green and selective synthesis of N-substituted amides using water-soluble porphyrazinato copper(II) catalyst. J Braz Chem Soc 24:895
78. Murahashi SI, Naota T, Saito E (1986) Ruthenium-catalyzed amidation of nitriles with amines. A novel, facile route to amides and polyamides. J Am Chem Soc 108:7846
79. van Dijk AJM, Heyligen T, Duchateau R, Meuldijk J, Koning CE (2007) Polyamide synthesis from 6-aminocapronitrile, part 1: N-alkyl amide formation by amine amidation of a hydro-lyzed nitrile. Chem Eur J 13:7664
80. Field L, Hughmark PB, Shumaker SH, Marshall WS (1961) Isomerization of aldoximes to amides under substantially neutral conditions. J Am Chem Soc 83:1983
81. Park S, Choi Y, Han H, Yang SH, Chang S (2003) Rh-catalyzed one-pot and practical transformation of aldoximes to amides. Chem Commun 1936
82. Allen CL, Lawrence R, Emmett L, Williams JMJ (2011) Mechanistic studies into metal-catalyzed aldoxime to amide rearrangement. Adv Synth Catal 353:3262
83. Okano T, Fujiwara K, Konishi H, Kiji J (1982) Application of the water-gas shift reaction. III. Reduction of oxidized nitrogen compounds with CO and H2O catalyzed by [Ru(cod)py4] (BPh4)2. Bull Chem Soc Jpn 55:1975
84. Owston NA, Parker AJ, Williams JMJ (2007) Highly efficient ruthenium-catalyzed oxime to amide rearrangement. Org Lett 9:3599
85. Gnanamgari D, Crabtree RH (2009) Terpyridine ruthenium-catalyzed one-pot conversion of aldehydes into amides. Organometallics 28:922
86. Kumar P, Singh AK, Pandey R, Pandey DS (2011) Bio-catalysts and catalysts based on ruthenium(II) polypyridyl complexes imparting diphenyl-(2-pyridyl)-phosphine as a co-ligand. J Organomet Chem 696:3454
87. Raja N, Raja MU, Ramesh R (2012) Ruthenium(II) NNO pincer type catalyst for the conversion of aldehydes to amides. Inorg Chem Commun 19:51
88. Prabhu RN, Ramesh R (2012) Ruthenium(II) carbonyl complexes containing benzhydrazone ligands: Synthesis, structure and facile one-pot conversion of aldehydes to amides. RSC Adv 2:4515
89. Manikandan R, Prakash G, Kathirvel R, Viswanathamurthi P (2013) Ruthenium(II) carbonyl complexes bearing quinoline-based NNO tridentate ligands as catalyst for one-pot conversion of aldehydes to amides and O-allylation of phenols. Spectrochim Acta A 116:501
90. Hull JF, Hilton ST, Crabtree RH (2010) A simple Ru catalyst for the conversion of aldehydes or oximes to primary amides. Inorg Chim Acta 363:1243
91. García-Alvarez R, Díaz-Alvarez AE, Borge J, Crochet P, Cadierno V (2012) Ruthenium- catalyzed rearrangement of aldoximes to primary amides in water. Organometallics 31:6482
92. García-Alvarez R, Díaz-Alvarez AE, Crochet P, Cadierno V (2013) Ruthenium-catalyzed one-pot synthesis of primary amides from aldehydes in water. RSC Adv 3:5889
93. Li F, Qu P, Ma J, Zou X, Sun C (2013) Tandem synthesis of N-alkylated amides from aldoximes and alcohols by using a Ru/Ir dual-catalyst system. ChemCatChem 5:2178
94. Chen C, Hong SH (2011) Oxidative amide synthesis directly from alcohols with amines. Org Biomol Chem 9:20
95. Gunanathan C, Milstein D (2013) Applications of acceptorless dehydrogenation and related transformations in chemical synthesis. Science 341:249
96. Dobereiner GE, Crabtree RH (2010) Dehydrogenation as a substrate-activating strategy in homogeneous transition-metal catalysis. Chem Rev 110:681
97. Gnanaprakasam B, Zhang J, Milstein D (2010) Direct synthesis of imines from alcohols and amines with liberation of H2. Angew Chem Int Ed 49:1468
98. Marr AC (2012) Organometallic hydrogen transfer and dehydrogenation catalysts for the conversion of bio-renewable alcohols. Catal Sci Technol 2:279
99. Naota T, Murahashi SI (1991) Ruthenium-catalyzed transformations of amino alcohols to lactams. Synlett 693
100. Fujita K-I, Takahashi Y, Owaki M, Yamamoto K, Yamaguchi R (2004) Synthesis of five-, six-, and seven-membered ring lactams by Cp*Rh complex-catalyzed oxidative N-heterocyclization of amino alcohols. Org Lett 6:2785
101. Gunanathan C, Ben-David Y, Milstein D (2007) Direct synthesis of amides from alcohols and amines with liberation of H2. Science 317:790
102. Gunanathan C, Milstein D (2011) Bond activation by metal-ligand cooperation: Design of “green” catalytic reactions based on aromatization-dearomatization of pincer complexes. Top Organomet Chem 37:55
103. Gunanathan C, Milstein D (2011) Metal-ligand cooperation by aromatization-dearomatization: a new paradigm in bond activation and “green” catalysis. Acc Chem Res 44:588
104. Milstein D (2010) Discovery of environmentally benign catalytic reactions of alcohols catalyzed by pyridine-based pincer Ru complexes, based on metal-ligand cooperation. Top Catal 53:915
105. Li H, Wang X, Huang F, Lu G, Jiang J, Wang ZX (2011) Computational study on the catalytic role of pincer ruthenium(II)-PNN complex in directly synthesizing amide from alcohol and amine: the origine of selectivity of amide over ester and imine. Organometallics 30:5233
106. Zeng G, Li S (2011) Insights into dehydrogenative coupling of alcohols and amines catalyzed by a (PNN)-Ru(II) hydride complex: unusual metal-ligand cooperation. Inorg Chem 50:10572
107. Cho D, Ko KC, Lee JY (2013) Catalytic mechanism for the ruthenium-complex-catalyzed synthesis of amides from alcohols and amines: a DFT study. Organometallics 32:4571
108. Zeng H, Guan Z (2011) Direct synthesis of polyamides via catalytic dehydrogenation of diols and diamines. J Am Chem Soc 133:1159
109. Gnanaprakasam B, Balaraman E, Gunanathan C, Milstein D (2012) Synthesis of polyamides from diols and diamines with liberation of H2. J Poly Sci Part A Polymer Chem 50:1755
110. Milstein D, Balaraman E, Gunanathan C, Gnanaprakasam B, Zhang J (2012) Novel ruthenium complexes and their uses in processes for formation and/or hydrogenation of esters, amides and derivatives thereof. PCT Int Appl WO 2012052996
111. Gnanaprakasam B, Balaraman E, Ben-David Y, Milstein D (2011) Synthesis of peptides and pyrazines from β-amino alcohols through extrusion of H2 catalyzed by ruthenium pincer complexes: Ligands-controlled selectivity. Angew Chem Int Ed 50:12240
112. Zweifel T, Naubron JV, Grützmacher H (2009) Catalyzed dehydrogenative coupling of primary alcohols with water, methanol, or amines. Angew Chem Int Ed 48:559
113. Shimizu KI, Ohshima K, Satsuma A (2009) Direct dehydrogenative amide synthesis from alcohols and amines catalyzed by γ-alumina supported silver cluster. Chem Eur J 15:9977
114. Nordstrøm LU, Vogt H, Madsen R (2008) Amide synthesis from alcohols and amines by the extrusion of dihydrogen. J Am Chem Soc 130:17672
115. Ghosh SC, Muthaiah S, Zhang Y, Xu X, Hong SH (2009) Direct amide synthesis from alcohols and amines by phosphine-free ruthenium catalyst systems. Adv Synth Catal 351:2643
116. Ghosh SC, Hong SH (2010) Simple RuCl3-catalyzed amide synthesis from alcohols and amines. Eur J Org Chem 4266
117. Dam JH, Osztrovszky G, Nordstrøm LU, Madsen R (2010) Amide synthesis from alcohols and amines catalyzed by ruthenium N-heterocyclic carbene complexes. Chem Eur J 16:6820
118. Zhang J, Senthilkumar M, Ghosh SC, Hong SH (2010) Synthesis of cyclic imides from simple diols. Angew Chem Int Ed 49:6391
119. Muthaiah S, Ghosh SC, Jee JE, Chen C, Zhang J, Hong SH (2010) Direct amides synthesis from either alcohols or aldehydes with amines: activity of Ru(II) hydride and Ru(0) complexes. J Org Chem 75:3002
120. Makarov IS, Fristrup P, Madsen R (2012) Mechanistic investigation of ruthenium-N-hetero-cyclic-carbene-catalyzed amidation of amines with alcohols. Chem Eur J 18:15683
121. Prechtl MHG, Wobser K, Theyssen N, Ben-David Y, Milstein D, Leitner W (2012) Direct coupling of alcohols to form esters and amides with evolution of H2 using in situ formed ruthenium catalysts. Catal Sci Technol 2:2039
122. Pingen D, Vogt D (2014) Amino-alcohols cyclization: Selective synthesis of lactams and cyclic amines from amino-alcohols. Catal Sci Technol 4:47
123. Watson AJA, Maxwell AC, Williams JMJ (2009) Ruthenium-catalyzed oxidation of alcohols into amides. Org Lett 11:2667
124. Zhang Y, Chen C, Ghosh SC, Li Y, Hong SH (2010) Well-defined N-heterocyclic carbene based ruthenium catalysts for direct amide synthesis from alcohols and amines. Organome-tallics 29:1374
125. Chen C, Zhang Y, Hongs H (2011) N-heterocyclic carbene based ruthenium-catalyzed direct amide synthesis from alcohols and secondary amines: involvement of esters. J Org Chem 76:10005
126. Prades A, Peris E, Albrecht M (2011) Oxidations and oxidative couplings catalyzed by triazolylidene ruthenium complexes. Organometallics 30:1162
127. Schley N, Dobereiner GE, Crabtree RH (2011) Oxidative synthesis of amides and pyrroles via dehydrogenative alcohol oxidation by ruthenium diphosphine diamine complexes. Organ-ometallics 30:4174
128. Nova A, Balcells D, Schley ND, Dobereiner GE, Crabtree RH, Eisenstein O (2010) An experimental-theoretical study of the factors that affect the switch between ruthenium-catalyzed dehydrogenative amide formation versus amine alkylation. Organometallics 29:6548
129. Srimani D, Balaraman E, Hu P, Ben-David Y, Milstein D (2013) Formation of tertiary amides and dihydrogen by dehydrogenative coupling of primary alcohols with secondary amines catalyzed by ruthenium bipyridine-based pincer complexes. Adv Synth Catal 355:2525
130. Ortega N, Richter C, Glorius F (2013) N-formylation of amines by methanol activation. Org Lett 15:1776
131. Malineni J, Merkens C, Keul H, Möller M (2013) An efficient N-heterocyclic carbene based ruthenium-catalyst: application towards the synthesis of esters and amides. Catal Commun 40:80
132. Wang Y, Zhu D, Tang L, Wang S, Wang Z (2011) Highly efficient amide synthesis from alcohols and amines by virtue of a water-soluble gold/DNA catalyst. Angew Chem Int Ed 50:8917
133. Oishi T, Yamaguchi K, Mizuno N (2010) An efficient one-pot synthesis of nitriles from alcohols or aldehydes with NH3 catalyzed by a supported ruthenium hydroxide. Top Catal 53:479
134. Fu Z, Lee J, Kang B, Hong SH (2012) Dehydrogenative amide synthesis: azide as a nitrogen source. Org Lett 14:6028
135. Kang B, Fu Z, Hong SH (2013) Ruthenium-catalyzed redox-neutral and single-step amide synthesis from alcohol and nitrile with complete atom economy. J Am Chem Soc 135:11704
136. Varma RS, Naicker KP (1999) Solvent-free synthesis of amides from non-enolizable esters and amines using microwave irradiation. Tetrahedron Lett 40:6177
137. Gnanaprakasam B, Milstein D (2011) Synthesis of amides from esters and amines with liberation of H2 under neutral conditions. J Am Chem Soc 133:1682
138. Yamaguchi K, Mizuno N (2010) Green functional group transformations by supported ruthenium hydroxide catalysts. Synlett 2365
139. Schümperli MT, Hammond C, Hermans I (2012) Developments in the aerobic oxidation of amines. ACS Catal 2:1108
140. Kim JW, Yamaguchi K, Mizuno N (2008) Heterogeneously catalyzed efficient oxygenation of primary amines to amides by a supported ruthenium hydroxide catalyst. Angew Chem Int Ed 47:9249
141. He J, Yamaguchi K, Mizuno N (2011) Aerobic oxidative transformation of primary azides to nitriles by ruthenium hydroxide catalyst. J Org Chem 76:4606
142. Chang JWW, Chan PWH (2008) Highly efficient ruthenium(II) porphyrin catalyzed amidation of aldehydes. Angew Chem Int Ed 47:1138
143. Muralirajan K, Parthasarathy K, Cheng CH (2012) Ru(II)-catalyzed amidation of 2-arylpyridines with isocyanates via C-H activation. Org Lett 14:4262
144. Tang W, Capacci A, Sarvestani M, Wei X, Yee NK, Senanayake CH (2009) A facile and practical synthesis of N-acetyl enamides. J Org Chem 74:9528
145. Murugan K, Huang DW, Chien YT, Liu ST (2013) An efficient preparation of N-acetyl enamides catalyzed by Ru(II) complexes. Tetrahedron 69:268