46. Astruc D, Lu F, Aranzaes JR (2005) Nanoparticles as recyclable catalysts: the frontier between
homogeneous and heterogeneous catalysis. Angew Chem Int Ed 44:7852–7872. https://doi.
org/10.1002/anie.200500766
47. Alonso F, Moglie Y, Radivoy G, Yus M (2013) Alkenes as azido precursors for the one-pot
synthesis of 1,2,3-triazoles catalyzed by copper nanoparticles on activated carbon. J Org Chem
78:5031–5037. https://doi.org/10.1021/jo400110m
48. Alonso F, Moglie Y, Radivoy G, Yus M (2011) Multicomponent click synthesis of 1,2,3triazoles from epoxides in water catalyzed by copper nanoparticles on activated carbon. J Org
Chem 76:8394–8405. https://doi.org/10.1021/jo2016339
49. Nador F, Volpe MA, Alonso F, Feldhoff A, Kirschning A, Radivoy G (2013)
Copper nanoparticles supported on silica coated maghemite as versatile, magnetically
recoverable and reusable catalyst for alkyne coupling and cycloaddition reactions. Appl
Catal A Gen 455:39–45. https://doi.org/10.1016/j.apcata.2013.01.023
50. Alonso F, Moglie Y, Radivoy G, Yus M (2010) Multicomponent synthesis of 1,2,3-triazoles in
water catalyzed by copper nanoparticles on activated carbon. Adv Synth Catal
352:3208–3214. https://doi.org/10.1002/adsc.201000637
51. Fu F, Martinez A, Wang C, Ciganda R, Yate L, Escobar A, Moya S, Fouquet E, Ruiz J,
Astruc D (2017) Exposure to air boosts CuAAC reactions catalyzed by PEG-stabilized
Cu nanoparticles. Chem Commun 53:5384–5387. https://doi.org/10.1039/C7CC02504A
52. Adenot A, Landstrom EB, Gallou F, Lipshutz BH (2017) Fe/ppm Cu nanoparticles as
a recyclable catalyst for click reactions in water at room temperature. Green Chem
19:2506–2509. https://doi.org/10.1039/C7GC00883J
53. Pourjavadi A, Tajbakhsh M, Farhang M, Hosseini SH (2015) Copper-loaded polymeric
magnetic nanocatalysts as retrievable and robust heterogeneous catalysts for click reactions.
New J Chem 39:4591–4600. https://doi.org/10.1039/C4NJ02134G
54. Liu Y, Liu Z, Cui Y (2015) An efficient nanoparticle-supported and magnetically recoverable
copper(I) catalyst for synthesis of furans from Ene-Yne-Ketone. Chin J Chem 33:175–180.
https://doi.org/10.1002/cjoc.201400730
55. Wang K, Yang L, Zhao W, Cao L, Sun Z, Zhang F (2017) A facile synthesis of copper
nanoparticles supported on an ordered mesoporous polymer as an efficient and stable catalyst
for solvent-free Sonogashira coupling reactions. Green Chem 19:1949–1957. https://doi.org/
10.1039/C7GC00219J
56. Sharma RK, Gaur R, Yadav M, Rathi AK, Pechousek J, Petr M, Zboril R, Gawande MB
(2015) Maghemite-copper nanocomposites: applications for ligand-free cross-coupling (CÀO,
CÀS, and CÀN) reactions. ChemCatChem 7:3495–3502. https://doi.org/10.1002/cctc.
201500546
57. Ugi I, Meyr R, Fetzer U (1959) Versammlungsberichte. Angew Chem 71:373–388. https://doi.
org/10.1002/ange.19590711110
58. Ugi I, Steinbrückner C (1960) Über ein neues Kondensations-Prinzip. Angew Chem
72:267–268. https://doi.org/10.1002/ange.19600720709
59. Passerini M, Simone L (1921) Sopra gli isonitrili (I). Composto del p-isonitril-azobenzolo
con acetone ed acido acetico. Gazz Chim Ital 51:126–129
60. Biginelli P (1891) Ueber aldehyduramide des acetessigäthers. Ber Dtsch Chem Ges
24:1317–1319. https://doi.org/10.1002/cber.189102401228
61. Biginelli P (1891) Ueber aldehyduramide des acetessigäthers. II. Ber Dtsch Chem Ges
24:2962–2967. https://doi.org/10.1002/cber.189102402126
62. Sharghi H, Shiri P, Aberi M (2014) A solvent-free and one-pot strategy for ecocompatible
synthesis of substituted- benzofurans from various salicylaldehydes, secondary amines, and
nonactivated alkynes catalyzed by copper(I) oxide nanoparticles. Synthesis 46:2489–2498.
https://doi.org/10.1055/s-0034-1378206
63. Li J-H, Tang B-X, Tao L-M, Xie Y-X, Liang Y, Zhang M-B (2006) Reusable copper-catalyzed
cross-coupling reactions of aryl halides with organotins in inexpensive ionic liquids. J Org
Chem 71:7488–7490. https://doi.org/10.1021/jo061220j
Earth-Abundant and Precious Metal Nanoparticle Catalysis
125
homogeneous and heterogeneous catalysis. Angew Chem Int Ed 44:7852–7872. https://doi.
org/10.1002/anie.200500766
47. Alonso F, Moglie Y, Radivoy G, Yus M (2013) Alkenes as azido precursors for the one-pot
synthesis of 1,2,3-triazoles catalyzed by copper nanoparticles on activated carbon. J Org Chem
78:5031–5037. https://doi.org/10.1021/jo400110m
48. Alonso F, Moglie Y, Radivoy G, Yus M (2011) Multicomponent click synthesis of 1,2,3triazoles from epoxides in water catalyzed by copper nanoparticles on activated carbon. J Org
Chem 76:8394–8405. https://doi.org/10.1021/jo2016339
49. Nador F, Volpe MA, Alonso F, Feldhoff A, Kirschning A, Radivoy G (2013)
Copper nanoparticles supported on silica coated maghemite as versatile, magnetically
recoverable and reusable catalyst for alkyne coupling and cycloaddition reactions. Appl
Catal A Gen 455:39–45. https://doi.org/10.1016/j.apcata.2013.01.023
50. Alonso F, Moglie Y, Radivoy G, Yus M (2010) Multicomponent synthesis of 1,2,3-triazoles in
water catalyzed by copper nanoparticles on activated carbon. Adv Synth Catal
352:3208–3214. https://doi.org/10.1002/adsc.201000637
51. Fu F, Martinez A, Wang C, Ciganda R, Yate L, Escobar A, Moya S, Fouquet E, Ruiz J,
Astruc D (2017) Exposure to air boosts CuAAC reactions catalyzed by PEG-stabilized
Cu nanoparticles. Chem Commun 53:5384–5387. https://doi.org/10.1039/C7CC02504A
52. Adenot A, Landstrom EB, Gallou F, Lipshutz BH (2017) Fe/ppm Cu nanoparticles as
a recyclable catalyst for click reactions in water at room temperature. Green Chem
19:2506–2509. https://doi.org/10.1039/C7GC00883J
53. Pourjavadi A, Tajbakhsh M, Farhang M, Hosseini SH (2015) Copper-loaded polymeric
magnetic nanocatalysts as retrievable and robust heterogeneous catalysts for click reactions.
New J Chem 39:4591–4600. https://doi.org/10.1039/C4NJ02134G
54. Liu Y, Liu Z, Cui Y (2015) An efficient nanoparticle-supported and magnetically recoverable
copper(I) catalyst for synthesis of furans from Ene-Yne-Ketone. Chin J Chem 33:175–180.
https://doi.org/10.1002/cjoc.201400730
55. Wang K, Yang L, Zhao W, Cao L, Sun Z, Zhang F (2017) A facile synthesis of copper
nanoparticles supported on an ordered mesoporous polymer as an efficient and stable catalyst
for solvent-free Sonogashira coupling reactions. Green Chem 19:1949–1957. https://doi.org/
10.1039/C7GC00219J
56. Sharma RK, Gaur R, Yadav M, Rathi AK, Pechousek J, Petr M, Zboril R, Gawande MB
(2015) Maghemite-copper nanocomposites: applications for ligand-free cross-coupling (CÀO,
CÀS, and CÀN) reactions. ChemCatChem 7:3495–3502. https://doi.org/10.1002/cctc.
201500546
57. Ugi I, Meyr R, Fetzer U (1959) Versammlungsberichte. Angew Chem 71:373–388. https://doi.
org/10.1002/ange.19590711110
58. Ugi I, Steinbrückner C (1960) Über ein neues Kondensations-Prinzip. Angew Chem
72:267–268. https://doi.org/10.1002/ange.19600720709
59. Passerini M, Simone L (1921) Sopra gli isonitrili (I). Composto del p-isonitril-azobenzolo
con acetone ed acido acetico. Gazz Chim Ital 51:126–129
60. Biginelli P (1891) Ueber aldehyduramide des acetessigäthers. Ber Dtsch Chem Ges
24:1317–1319. https://doi.org/10.1002/cber.189102401228
61. Biginelli P (1891) Ueber aldehyduramide des acetessigäthers. II. Ber Dtsch Chem Ges
24:2962–2967. https://doi.org/10.1002/cber.189102402126
62. Sharghi H, Shiri P, Aberi M (2014) A solvent-free and one-pot strategy for ecocompatible
synthesis of substituted- benzofurans from various salicylaldehydes, secondary amines, and
nonactivated alkynes catalyzed by copper(I) oxide nanoparticles. Synthesis 46:2489–2498.
https://doi.org/10.1055/s-0034-1378206
63. Li J-H, Tang B-X, Tao L-M, Xie Y-X, Liang Y, Zhang M-B (2006) Reusable copper-catalyzed
cross-coupling reactions of aryl halides with organotins in inexpensive ionic liquids. J Org
Chem 71:7488–7490. https://doi.org/10.1021/jo061220j
Earth-Abundant and Precious Metal Nanoparticle Catalysis
125