11. Durand J, Teuma E, Gómez M (2008) An overview of palladium nanocatalysts: surface
and molecular reactivity. Eur J Inorg Chem 2008:3577–3586. https://doi.org/10.1002/ejic.
200800569
12. Torborg C, Beller M (2009) Recent applications of palladium-catalyzed coupling reactions
in the pharmaceutical, agrochemical, and fine chemical industries. Adv Synth Catal
351:3027–3043. https://doi.org/10.1002/adsc.200900587
13. Narayanan R, El-Sayed MA (2003) Effect of catalysis on the stability of metallic
nanoparticles: Suzuki reaction catalyzed by PVP-palladium nanoparticles. J Am Chem Soc
125:8340–8347. https://doi.org/10.1021/ja035044x
14. Handa S, Wang Y, Gallou F, Lipshutz BH (2015) Sustainable Fe–ppm Pd nanoparticle
catalysis of Suzuki-Miyaura cross-couplings in water. Science 349:1087. https://doi.org/10.
1126/science.aac6936
15. Lipshutz BH (2017) The ‘Nano-to-Nano’ effect applied to organic synthesis in water.
Johns Matthey Technol Rev 61:196
16. Handa S, Jin B, Bora PP, Wang Y, Zhang X, Gallou F, Reilly J, Lipshutz BH (2019)
Sonogashira couplings catalyzed by Fe nanoparticles containing ppm levels of reusable Pd,
under mild aqueous Micellar conditions. ACS Catal 9:2423–2431. https://doi.org/10.1021/
acscatal.9b00007
17. Feng J, Handa S, Gallou F, Lipshutz BH (2016) Safe and selective nitro group reductions
catalyzed by sustainable and recyclable Fe/ppm Pd nanoparticles in water at room temperature.
Angew Chem Int Ed 55:8979–8983. https://doi.org/10.1002/anie.201604026
18. Gabriel CM, Parmentier M, Riegert C, Lanz M, Handa S, Lipshutz BH, Gallou F (2017)
Sustainable and scalable Fe/ppm Pd nanoparticle nitro group reductions in water at room
temperature. Org Process Res Dev 21:247–252. https://doi.org/10.1021/acs.oprd.6b00410
19. Pang H, Gallou F, Sohn H, Camacho-Bunquin J, Delferro M, Lipshutz BH (2018) Synergistic
effects in Fe nanoparticles doped with ppm levels of (Pd + Ni). A new catalyst for sustainable
nitro group reductions. Green Chem 20:130–135. https://doi.org/10.1039/C7GC02991H
20. Sun J, Wang J, Feng X, Yamamoto Y, Almansour AI, Arumugam N, Kumar RS, Bao M
(2018) Carboxylative Suzuki coupling reactions of benzyl chlorides with allyl pinacolborate
catalyzed by palladium nanoparticles. Chin J Catal 39:1258–1262. https://doi.org/10.1016/
S1872-2067(18)63045-1
21. Slack ED, Gabriel CM, Lipshutz BH (2014) A palladium nanoparticle–nanomicelle
combination for the stereoselective semihydrogenation of alkynes in water at room temperature. Angew Chem Int Ed 53:14051–14054. https://doi.org/10.1002/anie.201407723
22. Jeanne-Julien L, Astier E, Lai-Kuen R, Genta-Jouve G, Roulland E (2018) Palladium
nanoparticle-catalyzed stereoretentive cross-coupling of alkenyl sulfides with grignard
reagents. Org Lett 20:1430–1434. https://doi.org/10.1021/acs.orglett.8b00208
23. Dictionary of Natural Products (2007) Chapman and Hall/CRC, Boca Raton. Internet resource
24. Heijnen D, Tosi F, Vila C, Stuart MCA, Elsinga PH, Szymanski W, Feringa BL (2017)
Oxygen activated, palladium nanoparticle catalyzed, ultrafast cross-coupling of organolithium
reagents. Angew Chem Int Ed 56:3354–3359. https://doi.org/10.1002/anie.201700417
25. Li X, Gong X, Li Z, Chang H, Gao W, Wei W (2017) Ligand- and copper-free Sonogashira
and Heck couplings of (Het)aryl chlorides and bromides catalyzed by palladium nanoparticles
supported on in situ generated Al(OH)3. RSC Adv 7:2475–2479. https://doi.org/10.1039/
C6RA25416K
26. Gao W-Z, Xu Y, Chen Y, Fu W-F (2015) Highly efficient and selective photocatalytic
reduction of nitroarenes using the Ni2P/CdS catalyst under visible-light irradiation. Chem
Commun 51:13217–13220. https://doi.org/10.1039/C5CC04030B
27. Cai S, Duan H, Rong H, Wang D, Li L, He W, Li Y (2013) Highly active and selective
catalysis of bimetallic Rh3Ni1 nanoparticles in the hydrogenation of nitroarenes. ACS Catal
3:608–612. https://doi.org/10.1021/cs300689w
Earth-Abundant and Precious Metal Nanoparticle Catalysis
123
and molecular reactivity. Eur J Inorg Chem 2008:3577–3586. https://doi.org/10.1002/ejic.
200800569
12. Torborg C, Beller M (2009) Recent applications of palladium-catalyzed coupling reactions
in the pharmaceutical, agrochemical, and fine chemical industries. Adv Synth Catal
351:3027–3043. https://doi.org/10.1002/adsc.200900587
13. Narayanan R, El-Sayed MA (2003) Effect of catalysis on the stability of metallic
nanoparticles: Suzuki reaction catalyzed by PVP-palladium nanoparticles. J Am Chem Soc
125:8340–8347. https://doi.org/10.1021/ja035044x
14. Handa S, Wang Y, Gallou F, Lipshutz BH (2015) Sustainable Fe–ppm Pd nanoparticle
catalysis of Suzuki-Miyaura cross-couplings in water. Science 349:1087. https://doi.org/10.
1126/science.aac6936
15. Lipshutz BH (2017) The ‘Nano-to-Nano’ effect applied to organic synthesis in water.
Johns Matthey Technol Rev 61:196
16. Handa S, Jin B, Bora PP, Wang Y, Zhang X, Gallou F, Reilly J, Lipshutz BH (2019)
Sonogashira couplings catalyzed by Fe nanoparticles containing ppm levels of reusable Pd,
under mild aqueous Micellar conditions. ACS Catal 9:2423–2431. https://doi.org/10.1021/
acscatal.9b00007
17. Feng J, Handa S, Gallou F, Lipshutz BH (2016) Safe and selective nitro group reductions
catalyzed by sustainable and recyclable Fe/ppm Pd nanoparticles in water at room temperature.
Angew Chem Int Ed 55:8979–8983. https://doi.org/10.1002/anie.201604026
18. Gabriel CM, Parmentier M, Riegert C, Lanz M, Handa S, Lipshutz BH, Gallou F (2017)
Sustainable and scalable Fe/ppm Pd nanoparticle nitro group reductions in water at room
temperature. Org Process Res Dev 21:247–252. https://doi.org/10.1021/acs.oprd.6b00410
19. Pang H, Gallou F, Sohn H, Camacho-Bunquin J, Delferro M, Lipshutz BH (2018) Synergistic
effects in Fe nanoparticles doped with ppm levels of (Pd + Ni). A new catalyst for sustainable
nitro group reductions. Green Chem 20:130–135. https://doi.org/10.1039/C7GC02991H
20. Sun J, Wang J, Feng X, Yamamoto Y, Almansour AI, Arumugam N, Kumar RS, Bao M
(2018) Carboxylative Suzuki coupling reactions of benzyl chlorides with allyl pinacolborate
catalyzed by palladium nanoparticles. Chin J Catal 39:1258–1262. https://doi.org/10.1016/
S1872-2067(18)63045-1
21. Slack ED, Gabriel CM, Lipshutz BH (2014) A palladium nanoparticle–nanomicelle
combination for the stereoselective semihydrogenation of alkynes in water at room temperature. Angew Chem Int Ed 53:14051–14054. https://doi.org/10.1002/anie.201407723
22. Jeanne-Julien L, Astier E, Lai-Kuen R, Genta-Jouve G, Roulland E (2018) Palladium
nanoparticle-catalyzed stereoretentive cross-coupling of alkenyl sulfides with grignard
reagents. Org Lett 20:1430–1434. https://doi.org/10.1021/acs.orglett.8b00208
23. Dictionary of Natural Products (2007) Chapman and Hall/CRC, Boca Raton. Internet resource
24. Heijnen D, Tosi F, Vila C, Stuart MCA, Elsinga PH, Szymanski W, Feringa BL (2017)
Oxygen activated, palladium nanoparticle catalyzed, ultrafast cross-coupling of organolithium
reagents. Angew Chem Int Ed 56:3354–3359. https://doi.org/10.1002/anie.201700417
25. Li X, Gong X, Li Z, Chang H, Gao W, Wei W (2017) Ligand- and copper-free Sonogashira
and Heck couplings of (Het)aryl chlorides and bromides catalyzed by palladium nanoparticles
supported on in situ generated Al(OH)3. RSC Adv 7:2475–2479. https://doi.org/10.1039/
C6RA25416K
26. Gao W-Z, Xu Y, Chen Y, Fu W-F (2015) Highly efficient and selective photocatalytic
reduction of nitroarenes using the Ni2P/CdS catalyst under visible-light irradiation. Chem
Commun 51:13217–13220. https://doi.org/10.1039/C5CC04030B
27. Cai S, Duan H, Rong H, Wang D, Li L, He W, Li Y (2013) Highly active and selective
catalysis of bimetallic Rh3Ni1 nanoparticles in the hydrogenation of nitroarenes. ACS Catal
3:608–612. https://doi.org/10.1021/cs300689w
Earth-Abundant and Precious Metal Nanoparticle Catalysis
123