Selective and reactive hydration of nitriles to amides in water using silver nanoparticles stabilized by organic ligands
Source abstract
Abstract
Water-dispersible silver nanoparticles stabilized by silver–carbon covalent bonds were prepared. They exhibited high catalytic activities for the selective hydration of nitriles to amides in water. The activation of a nitrile group by the functional groups of the substrates and the hydrophobic layer on the nanoparticles influenced the catalyzed reaction were confirmed. Alkyl nitriles could also be selectively hydrated.
Source: openaire · Quality: candidate unverified · Source record ↗
Research context
OpenAlex topics: Nanomaterials for catalytic reactions · Asymmetric Hydrogenation and Catalysis · Chemical Synthesis and Analysis
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
References (36)
Show source-provided references
1. Balcha T, Strobl JR, Fowler C, Dash P, Schott RWJ (2001) Selective aerobic oxidation of crotyl alcohol using AuPd core-shell nanoparticles. ACS Catal 1:425–43610.1021/cs200040a ↗
2. Berkovich Y, Garti N (1997) Catalytic colloidal Pd dispersions in water-organic solutions of quarternary ammonium salt. Colloids Surf A 128:91–9910.1016/S0927-7757(96)03911-8 ↗
3. Breslow R (1991) Hydrophobic effects on simple organic reactions in water. Acc Chem Res 24:159–16410.1021/ar00006a001 ↗
4. Buehler CA, Pearson DE (1970) Survey of orgnaic synthses, Chap 18. Wiley-Interscience, New York, pp 903–904
5. Chauhan GS, Sharma R, Lal H (2004) Synthesis and characterization of graft copolymers of hydroxypropyl cellulose with acrylamide and some comonomers. J Appl Polym Sci 91:545–55510.1002/app.13141 ↗
6. Chen D, Xiao X, Qiu X, Chen J (2009) Synthesis and electrical properties of uniform silver nanoparticles for electronic applications. J Mater Sci 44:1076–108110.1007/s10853-008-3204-y ↗
7. Chin C, Kim SY, Joo KS, Won G, Chong D (1999) Synthesis and catalytic activity of water-soluble iridium-sulfonated triphenylphosphine complex. hydration of nitriles. Bull Korean Chem Soc 20:535–538
8. Downs EL, Tyler DR (2014) Nanoparticle catalysts for nitrile hydration. Coord Chem Rev 280:28–3710.1016/j.ccr.2014.07.029 ↗
9. Gao Y, Jiang P, Song L, Lifeng L, Yan X, Zhou Z, Liu D, Wang J, Yuan H, Zhang Z, Zhao X, Dou X, Zhou W, Wang G, Xie S (2005) Growth mechanism of silver nanowires synthesized by polyvinylpyrrolidone-assisted polyol reduction. J Phys D Appl Phys 38:1061–106710.1088/0022-3727/38/7/015 ↗
10. Gohsh D, Chen S (2008) Palladium nanoparticles passivated by metal-carbon covalent linkages. Chem Mater 18:755–76210.1039/b715397j ↗
11. Huang X, Neretina S, El-Sayed MA (2009) Gold nanorods: from synthesis and properties to biological and biomedical applications. Adv Mater 21:4880–491010.1002/adma.200802789 ↗
12. Huang C, Zhou Y, Jin Y, Zhou X, Tang Z, Goub X, Zhou S (2011) Preparation and characterization of temperature-responsive and magnetic nanomicelles. J Mater Chem 21:5660–567010.1039/c0jm04264a ↗
13. Ishizuka A, Nakazaki Y, Oshiki T (2009) The hydration of nitriles catalyzed by the combination of palladium nanoparticles and copper compounds. Chem Lett 38:36010.1246/cl.2009.360 ↗
14. Jiang HL, Akita T, Ishida T, Haruta M, Xu Q (2011) Syntergistic catalysis of Au@Ag core-shell nanoparticles stabilized on metal-organic framework. J Am Chem Soc 133:1304–130610.1021/ja1099006 ↗
15. Kawai K, Kaneko K, Kawakami H, Narushima T, Matsumoto M, Hyono A, Nishihara H, Yonezawa T (2012) Synthesis and antibacterial properties of water-dispersible silver nanoparticles stabilized by metal–carbon σ-bond. Appl Surf Sci 262:7610.1016/j.apsusc.2012.02.018 ↗
16. Kim AY, Bae HS, Park S, Park S, Park KH (2011) Silver nanoparticle catalyzed selective hydrtion of nitriles to amides in water under neutral conditions. Catal Lett 141:685–69010.1007/s10562-011-0561-y ↗
17. Kobayashi S, Miyamura H (2010) Polymer-incarcerated metal(0) cluster catalysts. Chem Rec 10:271–29010.1002/tcr.201000026 ↗
18. Krutyakov YA, Kudrinsky AA, Olenin AY, Lisichkin GV (2010) Synthesis of highly stable silver colloids stabilized with water soluble sulfonated polyaniline. Appl Surf Sci 256:7037–704210.1016/j.apsusc.2010.05.020 ↗
19. Metin O, Durap F, Aydemir M, Saim Ozakara S (2011) Palladium(0) nanoclusters stabilized by poly(4-stylenesulfonic acid-co-maleic acid) as an effecive catalyst for Suzuki–Miyaura cross-coupling reactions in water. J Mol Catal A 337:39–4410.1016/j.molcata.2011.01.011 ↗
20. Mirkhalaf F, Paprotny J, Schiffrin DJ (2006) Synthesis of metal nanoparticles stablized by metal-carbon bonds. J Am Chem Soc 128:7400–740110.1021/ja058687g ↗
21. Mitsudome T, Mikami Y, Mori H, Akita S, Mizogaki T, Jitsukawa K, Kaneda K (2009) Supported silver nanoparticle catalyst for selective hydration of nitriles to amides in water. Chem Commun 22:3258–326010.1039/b902469g ↗
22. Mori K, Yamashita H (2011) Design of colloidal and supported metal nanoparticles: their synthesis, characterization, and catalytic application. J Jpn Pet Inst 54:1–1410.1627/jpi.54.1 ↗
23. Oshiki T, Yamashita H, Sawada K, Utsunomiya M, Takashi K, Takai K (2005) Dramatic rate acceleration by a diphenyl-2-pyridylphosphine ligand in the hydration of nitriles catalyzed by Ru(acac)2 compexes. Organometallics 24:6287–629010.1021/om050792b ↗
24. Rivara S, Lodola A, Mor M, Bedini A, Spadon IG, Lucini V, Pannacci M, Franchini F, Scaglione R, Sanchez RO, Gobbi G, Tarzia G (2007) N-(substituted-anilinoethyl)amides: design, synthesis, and pharmacological characterization of a new class of melatonin receptor ligands. J Med Chem 50:6618–662610.1021/jm700957j ↗
25. Sherbow TJ, Downs EL, Sayler RI, Razink JJ, Juliette JJ, Tyler DR (2014) Investigation of 1,3,5-triaza-7-phosphaadamantane-stabilized silver nanoparticles as catalysts for the hydration of benzonitriles and acetone cyanohydrin. ACS Catal 4:3096–310410.1021/cs500830s ↗
26. Sun Y (2013) Controlled synthesis of colloidal silver nanoparticles in organic solutions: empirical rules for nuleation engineering. Chem Soc Rev 42:2497–251110.1039/C2CS35289C ↗
27. Toshima N, Takahashi T (1992) Colloidal dispersions of platinum and palladium clusters embedded in micelles. preparation and application to the catalysis of hydrogenation of olefins. Bull Chem Soc Jpn 65:400–40910.1246/bcsj.65.400 ↗
28. Toshima N, Wang Y (1994) Preparaton and catalysis of novel colloidal dispersions of copper/noble metal bimetallic clusters. Langmuir 10:4574–458010.1021/la00024a031 ↗
29. Toshima N, Yonezawa T, Kushihashi K (1993) Polymer-protected palladium–platinum bimetallic clusters: preparation, catalytic properties and structural considerations. J Chem Soc Faraday Trans 89:2537–254310.1039/FT9938902537 ↗
30. Toshima N, Kanemaru M, Shiraishi Y, Koga Y (2005) Spontaneous formation of core/shell bimetallic nanoparticles: a calorimetric study. J Phys Chem B 109:16326–1633110.1021/jp051400h ↗
31. Yamaguchi K, Matsushita M, Mizuno N (2004) Efficient hydration of nitriles to amides in water, catalyzed by ruthenium hydroxide suported on alumina. Angew Chem 116(12):1576–158010.1002/anie.200353461 ↗
32. Yeung LK, Crooks RM (2001) Heck heterocoupling within a dendritic nanoreactor. Nano Lett 1:14–1710.1021/nl0001860 ↗
33. Yonezawa T, Genda H, Koumoto K (2003) Cationic silver nanoparticles dispersed in water prepared from insoluble salts. Chem Lett 32:194–19510.1246/cl.2003.194 ↗
34. Zhang Z, Zhao B, Hu L (1996) PVP protective mechanism of ultrafine silver powder synthesized by chemical reduction process. J Solid State Chem 121:105–11010.1006/jssc.1996.0015 ↗
35. Zhang JY, Wang XP, Liu HY, Tang JA, Jiang L (1998) Interfacial rheology investigation of polyacrylamide-surfactant interactions. Colloids Surf A 132:9–1610.1016/S0927-7757(97)00151-9 ↗
36. Zhu Y, Wu Z, Gayathri C, Qian H, Gil RR, Jin R (2010) Exploring stereoselectivity of Au25 nanoparticle catalyst for hydroganation of cyclic ketone. J Catal 271:155–16010.1016/j.jcat.2010.02.027 ↗