Carbon-catalysed reductive hydrogen atom transfer reactions

Nature Communications

Volumn 6, Issue , 2015, Pages

  Yang, Huimin ^a,b   Cui, Xinjiang ^a   Dai, Xingchao ^a,b   Deng, Youquan ^a   Shi, Feng ^a  

^a LANZHOU INSTITUTE OF CHEMICAL PHYSICS   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

[No Author keywords available]

Indexed keywords

2 PROPANOL; ALCOHOL; AMINE; BENZYL ALCOHOL; CARBON; HYDROGEN; KETONE; NITRO DERIVATIVE; NITROBENZENE; TRANSITION ELEMENT;

CARBON; CATALYST; HYDROGEN; METAL; PERFORMANCE ASSESSMENT;

ADSORPTION KINETICS; ALKYLATION; AMINATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CONTROLLED STUDY; DESORPTION; INFRARED SPECTROSCOPY; MASS FRAGMENTOGRAPHY; PROTON TRANSPORT; REACTION ANALYSIS; REDUCTION KINETICS; SCANNING ELECTRON MICROSCOPY; SURFACE PROPERTY; X RAY DIFFRACTION; X RAY PHOTOELECTRON SPECTROSCOPY;

EID: 84926379373     PISSN: None     EISSN: 20411723     Source Type: Journal    
DOI: 10.1038/ncomms7478     Document Type: Article

References (69)

1. Zewail, A. H. The Remarkable Phenomena of Hydrogen Transfer (WILEY-VCH, 2007).
2. Samec, J. S. M., Baeckvall, J.-E., Andersson, P. G. & Brandt, P. Mechanistic aspects of transition metal-catalyzed hydrogen transfer reactions. Chem. Soc. Rev. 35, 237-248 (2006).
3. Mayer, J. M. Understanding hydrogen atom transfer: from bond strengths to Marcus theory. Acc. Chem. Res. 44, 36-46 (2010).
4. Alonso, F., Riente, P. & Yus, M. Nickel nanoparticles in hydrogen transfer reactions. Acc. Chem. Res. 44, 379-391 (2011).
5. Dobereiner, G. E. & Crabtree, R. H. Dehydrogenation as a substrate-activating strategy in homogeneous transition-metal catalysis. Chem. Rev. 110, 681-703 (2010).
6. Blomberg, M. R. A. & Siegbahn, P. E. M. Different types of biological proton transfer reactions studied by quantum chemical methods. Biochim. Biophys. Acta 1757, 969-980 (2006).
7. Allen, C. L. & Williams, J. M. Metal-catalysed approaches to amide bond formation. Chem. Soc. Rev. 40, 3405-3415 (2011).
8. Bähn, S. et al. The catalytic amination of alcohols. ChemCatChem 3, 1853-1864 (2011).
9. Haag, D. & Kung, H. H. Metal free graphene based catalysts: a review. Top. Catal. 57, 762-773 (2014).
10. Shearer, C. J., Cherevan, A. & Eder, D. Application and future challenges of functional nanocarbon hybrids. Adv. Mater. 26, 2295-2318 (2014).
11. Kong, X. K., Chen, C. L. & Chen, Q. W. Doped graphene for metal-free Catalysis. Chem. Soc. Rev. 43, 2841-2857 (2014).
12. Zhang, J. et al. Surface-modified carbon nanotubes catalyze oxidative dehydrogenation of n-butane. Science 322, 73-77 (2008).
13. Frank, B., Morassutto, M., Schomaecker, R., Schloegl, R. & Su, D. S. Oxidative dehydrogenation of ethane over multiwalled carbon nanotubes. ChemCatChem 2, 644-648 (2010).
14. McGregor, J. et al. Active coke: carbonaceous materials as catalysts for alkane dehydrogenation. J. Catal. 269, 329-339 (2010).
15. Rinaldi, A. et al. Oxidative purification of carbon nanotubes and its impact on catalytic performance in oxidative dehydrogenation reactions. ChemSusChem 3, 254-260 (2010).
16. Dreyer, D. R., Jia, H. P. & Bielawski, C. W. Graphene oxide: a convenient carbocatalyst for facilitating oxidation and hydration reactions. Angew. Chem. Int. Ed. 49, 6813-6816 (2010).
17. Zhang, P., Gong, Y., Li, H., Chen, Z. & Wang, Y. Solvent-free aerobic oxidation of hydrocarbons and alcohols with Pd@N-doped carbon from glucose. Nat. Commun. 4, 1593 (2013).
18. Chen, Y., Zhang, J., Zhang, M. & Wang, X. Molecular and textural engineering of conjugated carbon nitride catalysts for selective oxidation of alcohols with visible light. Chem. Sci. 4, 3244-3248 (2013).
19. Huang, H. et al. Graphite oxide as an efficient and durable metal-free catalyst for aerobic oxidative coupling of amines to imines. Green Chem. 14, 930-934 (2012).
20. Dreyer, D. R., Jia, H.-P., Todd, A. D., Geng, J. & Bielawski, C. W. Graphite oxide: a selective and highly efficient oxidant of thiols and sulfides. Org. Biomol. Chem. 9, 7292-7295 (2011).
21. Chen, H. et al. Metal-free direct amidation of peptidyl thiol esters with α-amino acid esters. Green Chem. 13, 2723-2726 (2011).
22. Dhakshinamoorthy, A., Alvaro, M., Concepcion, P., Fornes, V. & Garcia, H. Graphene oxide as an acid catalyst for the room temperature ring opening of epoxides. Chem. Commun. 48, 5443-5445 (2012).
23. Qi, J., Xu, Y., Ma, N. & Sun, F. Graphite oxide-catalyzed esterification and transesterification. Chinese J. Org. Chem. 33, 1839-1846 (2013).
24. Dhakshinamoorthy, A., Alvaro, M., Puche, M., Fornes, V. & Garcia, H. Graphene oxide as catalyst for the acetalization of aldehydes at room temperature. ChemCatChem 4, 2026-2030 (2012).
25. Verma, S. et al. Graphene oxide: an efficient and reusable carbocatalyst for aza-Michael addition of amines to activated alkenes. Chem. Commun. 47, 12673-12675 (2011).
26. Acocella, M. R., Mauro, M., Falivene, L., Cavallo, L. & Guerra, G. Inverting the diastereoselectivity of the Mukaiyama-Michael addition with graphite-based catalysts. ACS Catal. 4, 492-496 (2014).
27. Kumar, A. V. & Rao, K. R. Recyclable graphite oxide catalyzed friedel-crafts addition of indoles to alpha, beta-unsaturated ketones. Tetrahedron Lett. 52, 5188-5191 (2011).
28. Chauhan, S. M. S. & Mishra, S. Use of graphite oxide and graphene oxide as catalysts in the synthesis of dipyrromethane and Calix 4 pyrrole. Molecules 16, 7256-7266 (2011).
29. Wang, H. et al. Graphene oxide as a facile acid catalyst for the one-pot conversion of carbohydrates into 5-ethoxymethylfurfural. Green Chem. 15, 2379-2383 (2013).
30. Basu, B., Kundu, S. & Sengupta, D. Graphene oxide as a carbocatalyst: the first example of a one-pot sequential dehydration-hydrothiolation of secondary aryl alcohols. RSC Adv. 3, 22130-22134 (2013).
31. Perhun, T. I., Bychko, I. B., Trypolsky, A. I. & Strizhak, P. E. Catalytic properties of graphene material in the hydrogenation of ethylene. Theor. Exp. Chem. 48, 367-370 (2013).
32. Pérez, M., Caputo, C. B., Dobrovetsky, R. & Stephan, D. W. Metal-free transfer hydrogenation of olefins via dehydrocoupling catalysis. Proc. Natl Acad. Sci. USA 111, 10917-10921 (2014).
33. Gao, Y., Ma, D., Wang, C., Guan, J. & Bao, X. Reduced graphene oxide as a catalyst for hydrogenation of nitrobenzene at room temperature. Chem. Commun. 47, 2432-2434 (2011).
34. Grigg, R., Mitchell, T. R. B., Sutthivaiyakit, S. & Tongpenyai, N. Transition metal-catalysed N -alkylation of amines by alcohols. J. Chem. Soc. Chem. Soc. 611-612 (1981).
35. Watanabe, Y., Tsuji, Y., Ige, H., Ohsugi, Y. & Ohta, T. Ruthenium-catalyzed N-alkylation and N-benzylation of aminoarenes with alcohols. J. Org. Chem. 49, 3359-3363 (1984).
36. Hamid, M. H. S. A. C. et al. Ruthenium-catalyzed N-alkylation of amines and sulfonamides using borrowing hydrogen methodology. J. Am. Chem. Soc. 131, 1766-1774 (2009).
37. Saidi, O. & Williams, J. M. J. Iridium-catalyzed hydrogen transfer reactions. Top. Organomet. Chem. 34, 77-106 (2011).
38. Kawahara, R., Fujita, K.-i. & Yamaguchi, R. N-alkylation of amines with alcohols catalyzed by a water-soluble Cp∗iridium complex: an efficient method for the synthesis of amines in aqueous media. Adv. Synth. Catal. 353, 1161-1168 (2011).
39. Lee, S. A., Kwak, S. H. & Lee, K. I. Highly enantioselective synthesis of cyclic sulfamidates and sulfamides via rhodium-catalyzed transfer hydrogenation. Chem. Commun. 47, 2372-2374 (2011).
40. Ghosh, R. & Sarkar, A. Palladium-catalyzed amination of allyl alcohols. J. Org. Chem. 76, 8508-8512 (2011).
41. Zhang, Y., Qi, X., Cui, X., Shi, F. & Deng, Y. Palladium catalyzed N-alkylation of amines with alcohols. Tetrahedron Lett. 52, 1334-1338 (2011).
42. Nagano, T. & Kobayashi, S. Palladium-catalyzed allylic amination using aqueous ammonia for the aynthesis of primary amines. J. Am. Chem. Soc. 131, 4200-4201 (2009).
43. 3-catalyzed highly efficient direct synthesis of secondary and tertiary amines and imines. Chem. Eur. J. 17, 13308-13317 (2011).
44. He, L. et al. Efficient and clean gold-catalyzed one-pot selective N-alkylation of amines with alcohols. Chem. Eur. J. 16, 13965-13969 (2010).
45. Shimizu, K.-I., Shimura, K., Nishimura, M. & Satsuma, A. Silver cluster-promoted heterogeneous copper catalyst for N-alkylation of amines with alcohols. RSC Adv. 1, 1310-1317 (2011).
46. Cui, X., Zhang, C., Shi, F. & Deng, Y. Au/Ag-Mo nano-rods catalyzed reductive coupling of nitrobenzenes and alcohols using glycerol as the hydrogen source. Chem. Commun. 48, 9391-9393 (2012).
47. Winans, C. F. & Adkins, H. The alkylation of amine as catalyzed by nickel. J. Am. Chem. Soc. 54, 306-312 (1932).
48. Shimizu, K.-i., Kon, K., Onodera, W., Yamazaki, H. & Kondo, J. N. Heterogeneous Ni catalyst for direct synthesis of primary amines from alcohols and ammonia. ACS Catal. 3, 112-117 (2013).
49. Shimizu, K.-i., Imaiida, N., Kon, K., Hakim Siddiki, S. M. A. & Satsuma, A. Heterogeneous Ni catalysts for N-alkylation of amines with alcohols. ACS Catal. 3, 998-1005 (2013).
50. Cui, X., Dai, X., Deng, Y. & Shi, F. Development of a general non-noble metal catalyst for the benign amination of alcohols with amines and ammonia. Chem. Eur. J. 19, 3665-3675 (2013).
51. Yamaguchi, K., Kobayashi, H., Oishi, T. & Mizuno, N. Heterogeneously catalyzed synthesis of primary amides directly from primary alcohols and aqueous ammonia. Angew. Chem. Int. Ed. 51, 544-547 (2012).
52. Yu, X., Liu, C., Jiang, L. & Xu, Q. Manganese dioxide catalyzed N-alkylation of sulfonamides and amines with alcohols under air. Org. Lett. 13, 6184-6187 (2011).
53. Kim, I., Itagaki, S., Jin, X., Yamaguchi, K. & Mizuno, N. Heterogeneously catalyzed self-condensation of primary amines to secondary amines by supported copper catalysts. Catal. Sci. Technol. 3, 2397-2403 (2013).
54. Martínez-Asencio, A., Ramón, D. J. & Yus, M. N-alkylation of poor nucleophilic amine and sulfonamide derivatives with alcohols by a hydrogen autotransfer process catalyzed by Copper(II) acetate. Tetrahedron Lett. 51, 325-327 (2010).
55. Jammi, S. et al. CuO nanoparticles catalyzed C-N, C-O, and C-S cross-coupling reactions: scope and mechanism. J. Org. Chem. 74, 1971-1976 (2009).
56. Cui, X. et al. Copper-catalyzed N-alkylation of sulfonamides with benzylic alcohols: catalysis and mechanistic studies. Adv. Synth. Catal. 351, 2949-2958 (2009).
57. Likhar, P. R., Arundhathi, R., Kantam, M. L. & Prathima, P. S. Amination of alcohols catalyzed by copper-aluminium hydrotalcite: a green synthesis of amines. Eur. J. Org. Chem. 5383-5389 (2009).
58. Shi, F. et al. Copper-catalyzed alkylation of sulfonamides with alcohols. Angew. Chem. Int. Ed. 48, 5912-5915 (2009).
59. Martinez, R., Ramon, D. J. & Yus, M. Selective N-monoalkylation of aromatic amines with benzylic alcohols by a hydrogen autotransfer process catalyzed by unmodified magnetite. Org. Biomol. Chem. 7, 2176-2181 (2009).
60. Zhao, Y., Foo, S. W. & Saito, S. Iron/amino acid catalyzed direct N-alkylation of amines with alcohols. Angew. Chem. Int. Ed. 50, 3006-3009 (2011).
61. Cui, X., Shi, F., Zhang, Y. & Deng, Y. Fe(II)-catalyzed N-alkylation of sulfonamides with benzylic alcohols. Tetrahedron Lett. 51, 2048-2051 (2010).
62. Sabater, S., Mata, J. A. & Peris, E. Dual catalysis with an IrIII-AuI heterodimetallic complex: reduction of nitroarenes by transfer hydrogenation using primary alcohols. Chem. Eur. J. 18, 6380-6385 (2012).
63. 4 cluster catalysts. Angew. Chem. Int. Ed. 51, 7794-7798 (2012).
64. Verho, O., Nagendiran, A., Tai, C.-W., Johnston, E. V. & Backvall, J.-E. Nanopalladium on amino-functionalized mesocellular foam as an efficient and recyclable catalyst for the selective transfer hydrogenation of nitroarenes to anilines. ChemCatChem 6, 205-211 (2014).
65. Hsu, S.-F. & Plietker, B. Selective transfer hydrogenation and hydrogenation of ketones using a defined monofunctional (P boolean and N(Bn)boolean and N(Bn)boolean and P)-Ru-II complex. Chem. Eur. J. 20, 4242-4245 (2014).
66. Wei, J. et al. Facile synthesis of hybrid core-shell nanospheres for the asymmetric transfer hydrogenation of aromatic ketones. ChemCatChem 6, 1368-1374 (2014).
67. Zell, T., Ben-David, Y. & Milstein, D. Unprecedented iron- catalyzed ester hydrogenation. mild, selective, and efficient hydrogenation of trifluoroacetic esters to alcohols catalyzed by an iron pincer complex. Angew. Chem. Int. Ed. 53, 4685-4689 (2014).
68. Larkin, P. Infrared and Raman Spectroscopy: Principles and Spectral Interpretation 126-127 (Elsevier, 2011).
69. Xuan, X. P., Wang, X. S. & Wang, N. Theoretical study of molecular structure and vibrational spectra of 1,4-dihydroxyanthraquinone. Spectrochim. Acta Part A 79, 1091-1098 (2011).