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80. de Souza ROMA, Bittar MS, Mendes LVP, da Silva CMF, da Silva VT, Antunes OAC (2008)
Copper-free Sonogashira reaction using gold nanoparticles supported on Ce2O3, Nb2O5
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81. Nafria R, Luo Z, Ibáñez M, Martí-Sànchez S, Yu X, de la Mata M, Llorca J, Arbiol J,
Kovalenko MV, Grabulosa A et al (2018) Growth of Au–Pd2Sn nanorods via galvanic
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82. Peshkov VA, Pereshivko OP, van der Eycken EV (2012) A walk around the A3-coupling.
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83. Ermolat’ev DS, Bariwal JB, Steenackers HPL, de Keersmaecker SCJ, Van der Eycken EV
(2010) Concise and diversity-oriented route toward polysubstituted 2-aminoimidazole alkaloids and their analogues. Angew Chem Int Ed 49:9465–9468. https://doi.org/10.1002/anie.
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84. Xu Q, Rozners E (2005) Asymmetric synthesis of trans-3,4-dialkyl-γ-butyrolactones via
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ol050578j
85. Kidwai M, Bansal V, Kumar A, Mozumdar S (2007) The first Au-nanoparticles catalyzed
green synthesis of propargylamines via a three-component coupling reaction of aldehyde,
alkyne and amine. Green Chem 9:742–745. https://doi.org/10.1039/B702287E
86. Huang J-L, Gray DG, Li C-J (2013) A3-coupling catalyzed by robust Au nanoparticles
covalently bonded to HS-functionalized cellulose nanocrystalline films. Beilstein J Org
Chem 9:1388–1396. https://doi.org/10.3762/bjoc.9.155
87. Chen Y, Liu C, Abroshan H, Li Z, Wang J, Li G, Haruta M (2016) Phosphine/phenylacetylideligated Au clusters for multicomponent coupling reactions. J Catal 340:287–294. https://doi.
org/10.1016/j.jcat.2016.05.023
88. Veisi H, Farokhi M, Hamelian M, Hemmati S (2018) Green synthesis of Au nanoparticles
using an aqueous extract of stachys lavandulifolia and their catalytic performance for alkyne/
aldehyde/amine A3 coupling reactions. RSC Adv 8:38186–38195. https://doi.org/10.1039/
C8RA06819D
89. Carrettin S, Blanco MC, Corma A, Hashmi ASK (2006) Heterogeneous goldcatalysed synthesis of phenols. Adv Synth Catal 348:1283–1288. https://doi.org/10.1002/
adsc.200606099
90. Gupta AK, Rhim CY, Oh CH, Mane RS, Han S-H (2006) Gold nanoparticle-catalysed [3 + 2]
dipolar cycloaddition of 1,6-allenynebenzaldehydes: construction of polycyclic ring systems.
Green Chem 8:25–28. https://doi.org/10.1039/B512034A
91. Gryparis C, Efe C, Raptis C, Lykakis IN, Stratakis M (2012) Cyclization of 1,6-enynes
catalyzed by gold nanoparticles supported on TiO2: significant changes in selectivity
and mechanism, as compared to homogeneous Au-catalysis. Org Lett 14:2956–2959. https://
doi.org/10.1021/ol301212j
92. U. S. Department of Health and Human Services, Food and Drug Administration, Center
for Drug Evaluation and Research (CDER), Center for Biologics Evaluation and Research
(CBER) (2015) Q3D elemental impurities guidance for industry
93. Gniewek A, Trzeciak AM (2013) Rh(0) nanoparticles: synthesis, structure and catalytic
application in Suzuki–Miyaura reaction and hydrogenation of benzene. Top Catal
56:1239–1245
94. Guha NR, Reddy CB, Aggarwal N, Sharma D, Shil AK, Bandna, Das P (2012) Solidsupported rhodium(0) nanoÀ/microparticles: an efficient ligand-free heterogeneous
catalyst for microwave-assisted Suzuki–Miyaura cross-coupling reaction. Adv Synth Catal
354:2911–2915
Earth-Abundant and Precious Metal Nanoparticle Catalysis
127
coupling reactions in water under aerobic conditions. Tetrahedron Lett 56:500–503. https://
doi.org/10.1016/j.tetlet.2014.12.041
80. de Souza ROMA, Bittar MS, Mendes LVP, da Silva CMF, da Silva VT, Antunes OAC (2008)
Copper-free Sonogashira reaction using gold nanoparticles supported on Ce2O3, Nb2O5
and SiO2 under microwave irradiation. Synlett 2008:1777–1780. https://doi.org/10.1055/s2008-1078565
81. Nafria R, Luo Z, Ibáñez M, Martí-Sànchez S, Yu X, de la Mata M, Llorca J, Arbiol J,
Kovalenko MV, Grabulosa A et al (2018) Growth of Au–Pd2Sn nanorods via galvanic
replacement and their catalytic performance on hydrogenation and sonogashira coupling
reactions. Langmuir 34:10634–10643. https://doi.org/10.1021/acs.langmuir.8b02023
82. Peshkov VA, Pereshivko OP, van der Eycken EV (2012) A walk around the A3-coupling.
Chem Soc Rev 41:3790–3807. https://doi.org/10.1039/C2CS15356D
83. Ermolat’ev DS, Bariwal JB, Steenackers HPL, de Keersmaecker SCJ, Van der Eycken EV
(2010) Concise and diversity-oriented route toward polysubstituted 2-aminoimidazole alkaloids and their analogues. Angew Chem Int Ed 49:9465–9468. https://doi.org/10.1002/anie.
201004256
84. Xu Q, Rozners E (2005) Asymmetric synthesis of trans-3,4-dialkyl-γ-butyrolactones via
an Acyl-Claisen and Iodolactonization route. Org Lett 7:2821–2824. https://doi.org/10.1021/
ol050578j
85. Kidwai M, Bansal V, Kumar A, Mozumdar S (2007) The first Au-nanoparticles catalyzed
green synthesis of propargylamines via a three-component coupling reaction of aldehyde,
alkyne and amine. Green Chem 9:742–745. https://doi.org/10.1039/B702287E
86. Huang J-L, Gray DG, Li C-J (2013) A3-coupling catalyzed by robust Au nanoparticles
covalently bonded to HS-functionalized cellulose nanocrystalline films. Beilstein J Org
Chem 9:1388–1396. https://doi.org/10.3762/bjoc.9.155
87. Chen Y, Liu C, Abroshan H, Li Z, Wang J, Li G, Haruta M (2016) Phosphine/phenylacetylideligated Au clusters for multicomponent coupling reactions. J Catal 340:287–294. https://doi.
org/10.1016/j.jcat.2016.05.023
88. Veisi H, Farokhi M, Hamelian M, Hemmati S (2018) Green synthesis of Au nanoparticles
using an aqueous extract of stachys lavandulifolia and their catalytic performance for alkyne/
aldehyde/amine A3 coupling reactions. RSC Adv 8:38186–38195. https://doi.org/10.1039/
C8RA06819D
89. Carrettin S, Blanco MC, Corma A, Hashmi ASK (2006) Heterogeneous goldcatalysed synthesis of phenols. Adv Synth Catal 348:1283–1288. https://doi.org/10.1002/
adsc.200606099
90. Gupta AK, Rhim CY, Oh CH, Mane RS, Han S-H (2006) Gold nanoparticle-catalysed [3 + 2]
dipolar cycloaddition of 1,6-allenynebenzaldehydes: construction of polycyclic ring systems.
Green Chem 8:25–28. https://doi.org/10.1039/B512034A
91. Gryparis C, Efe C, Raptis C, Lykakis IN, Stratakis M (2012) Cyclization of 1,6-enynes
catalyzed by gold nanoparticles supported on TiO2: significant changes in selectivity
and mechanism, as compared to homogeneous Au-catalysis. Org Lett 14:2956–2959. https://
doi.org/10.1021/ol301212j
92. U. S. Department of Health and Human Services, Food and Drug Administration, Center
for Drug Evaluation and Research (CDER), Center for Biologics Evaluation and Research
(CBER) (2015) Q3D elemental impurities guidance for industry
93. Gniewek A, Trzeciak AM (2013) Rh(0) nanoparticles: synthesis, structure and catalytic
application in Suzuki–Miyaura reaction and hydrogenation of benzene. Top Catal
56:1239–1245
94. Guha NR, Reddy CB, Aggarwal N, Sharma D, Shil AK, Bandna, Das P (2012) Solidsupported rhodium(0) nanoÀ/microparticles: an efficient ligand-free heterogeneous
catalyst for microwave-assisted Suzuki–Miyaura cross-coupling reaction. Adv Synth Catal
354:2911–2915
Earth-Abundant and Precious Metal Nanoparticle Catalysis
127