10 Progress in the Selective Semi-hydrogenation of Alkynes …
339
80. Rangheard C, de Julian Fernandez C, Phua P-H, Hoorn J, Lefort L, de Vries JG (2010) At
the frontier between heterogeneous and homogeneous catalysis: hydrogenation of olefins and
alkynes with soluble iron nanoparticles. Dalton Trans 39(36):8464–8471. https://doi.org/10.
1039/c0dt00177e
81. Gregori BJ, Schwarzhuber F, Pöllath S, Zweck J, Fritsch L, Schoch R, Bauer M,
Jacobi von Wangelin A (2019) Stereoselective alkyne hydrogenation by using a simple iron
catalyst. ChemSusChem 12(16):3864–3870. https://doi.org/10.1002/cssc.201900926
82. Hudson R, Riviere A, Cirtiu CM, Luska KL, Moores A (2012) Iron-iron oxide core-shell
nanoparticles are active and magnetically recyclable olefin and alkyne hydrogenation catalysts
in protic and aqueous media. Chem Commun 48(27):3360–3362. https://doi.org/10.1039/c2c
c16438h
83. Cirtiu CM, Raychoudhury T, Ghoshal S, Moores A (2011) Systematic comparison of the
size, surface characteristics and colloidal stability of zero valent iron nanoparticles pre- and
post-grafted with common polymers. Colloids Surf A 390(1–3):95–104. https://doi.org/10.
1016/j.colsurfa.2011.09.011
84. Gieshoff TN, Welther A, Kessler MT, Prechtl MHG, Jacobi von Wangelin A (2014) Stereoselective iron-catalyzed alkyne hydrogenation in ionic liquids. Chem Commun 50(18):2261–
2264. https://doi.org/10.1039/c3cc49679a
85. Kelsen V, Wendt B, Werkmeister S, Junge K, Beller M, Chaudret B (2013) The use of ultrasmall iron(0) nanoparticles as catalysts for the selective hydrogenation of unsaturated C–C
bonds. Chem Commun 49(33):3416–3418. https://doi.org/10.1039/c3cc00152k
86. Liu Y, Zhao J, Feng J, He Y, Du Y, Li D (2018) Layered double hydroxide-derived Ni–Cu
nanoalloy catalysts for semi-hydrogenation of alkynes: Improvement of selectivity and anticoking ability via alloying of Ni and Cu. J Catal 359:251–260. https://doi.org/10.1016/j.jcat.
2018.01.009
87. Bruno JE, Dwarica NS, Whittaker TN, Hand ER, Guzman CS, Dasgupta A, Chen Z, Rioux
RM, Chandler BD (2020) Supported Ni–Au colloid precursors for active, selective, and stable
alkyne partial hydrogenation catalysts. ACS Catal 10(4):2565–2580. https://doi.org/10.1021/
acscatal.9b05402
88. Brown CA, Brown HC (1963) The reaction of sodium borohydride with nickel acetate
in aqueous solution—a convenient synthesis of an active nickel hydrogenation catalyst of
low isomerizing tendency. J Am Chem Soc 85(7):1003–1005. https://doi.org/10.1021/ja0089
0a040
89. Brown HC, Brown CA (1963) The reaction of sodium borohydride with nickel acetate
in ethanol solution—a highly selective nickel hydrogenation catalyst. J Am Chem Soc
85(7):1005–1006. https://doi.org/10.1021/ja00890a041
90. Brown HC, Brown CA (1966) Catalytic hydrogenation—I: the reaction of platinum metal
salts with sodium borohydride—new active platinum metal catalysts for hydrogenation.
Tetrahedron 22, Supplement 8(0):149–164. http://dx.doi.org/10.1016/S0040-4020(01)821
80-3
91. Brown CA (1970) The hydrogenation of hex-1-yne over borohydride-reduced catalysts.
Evidence concerning the mechanism of reduction. J Chem Soc D Chem Commun 3:139–140.
https://doi.org/10.1039/c29700000139
92. Albani D, Karajovic K, Tata B, Li Q, Mitchell S, Lopez N, Perez-Ramirez J (2019)
Ensemble design in nickel phosphide catalysts for alkyne semi-hydrogenation. ChemCatChem
11(1):457–464. https://doi.org/10.1002/cctc.201801430
93. Zhao M (2016) Fabrication of ultrafine palladium phosphide nanoparticles as highly active
catalyst for chemoselective hydrogenation of alkynes. Chem Asian J 11(4):461–464. https://
doi.org/10.1002/asia.201500939
94. Zhao M, Ji Y, Wang M, Zhong N, Kang Z, Asao N, Jiang W-J, Chen Q (2017) Compositiondependent morphology of bi- and trimetallic phosphides: construction of amorphous Pd–
Cu–Ni–P nanoparticles as a selective and versatile catalyst. ACS Appl Mater Interfaces
9(40):34804–34811. https://doi.org/10.1021/acsami.7b08082
339
80. Rangheard C, de Julian Fernandez C, Phua P-H, Hoorn J, Lefort L, de Vries JG (2010) At
the frontier between heterogeneous and homogeneous catalysis: hydrogenation of olefins and
alkynes with soluble iron nanoparticles. Dalton Trans 39(36):8464–8471. https://doi.org/10.
1039/c0dt00177e
81. Gregori BJ, Schwarzhuber F, Pöllath S, Zweck J, Fritsch L, Schoch R, Bauer M,
Jacobi von Wangelin A (2019) Stereoselective alkyne hydrogenation by using a simple iron
catalyst. ChemSusChem 12(16):3864–3870. https://doi.org/10.1002/cssc.201900926
82. Hudson R, Riviere A, Cirtiu CM, Luska KL, Moores A (2012) Iron-iron oxide core-shell
nanoparticles are active and magnetically recyclable olefin and alkyne hydrogenation catalysts
in protic and aqueous media. Chem Commun 48(27):3360–3362. https://doi.org/10.1039/c2c
c16438h
83. Cirtiu CM, Raychoudhury T, Ghoshal S, Moores A (2011) Systematic comparison of the
size, surface characteristics and colloidal stability of zero valent iron nanoparticles pre- and
post-grafted with common polymers. Colloids Surf A 390(1–3):95–104. https://doi.org/10.
1016/j.colsurfa.2011.09.011
84. Gieshoff TN, Welther A, Kessler MT, Prechtl MHG, Jacobi von Wangelin A (2014) Stereoselective iron-catalyzed alkyne hydrogenation in ionic liquids. Chem Commun 50(18):2261–
2264. https://doi.org/10.1039/c3cc49679a
85. Kelsen V, Wendt B, Werkmeister S, Junge K, Beller M, Chaudret B (2013) The use of ultrasmall iron(0) nanoparticles as catalysts for the selective hydrogenation of unsaturated C–C
bonds. Chem Commun 49(33):3416–3418. https://doi.org/10.1039/c3cc00152k
86. Liu Y, Zhao J, Feng J, He Y, Du Y, Li D (2018) Layered double hydroxide-derived Ni–Cu
nanoalloy catalysts for semi-hydrogenation of alkynes: Improvement of selectivity and anticoking ability via alloying of Ni and Cu. J Catal 359:251–260. https://doi.org/10.1016/j.jcat.
2018.01.009
87. Bruno JE, Dwarica NS, Whittaker TN, Hand ER, Guzman CS, Dasgupta A, Chen Z, Rioux
RM, Chandler BD (2020) Supported Ni–Au colloid precursors for active, selective, and stable
alkyne partial hydrogenation catalysts. ACS Catal 10(4):2565–2580. https://doi.org/10.1021/
acscatal.9b05402
88. Brown CA, Brown HC (1963) The reaction of sodium borohydride with nickel acetate
in aqueous solution—a convenient synthesis of an active nickel hydrogenation catalyst of
low isomerizing tendency. J Am Chem Soc 85(7):1003–1005. https://doi.org/10.1021/ja0089
0a040
89. Brown HC, Brown CA (1963) The reaction of sodium borohydride with nickel acetate
in ethanol solution—a highly selective nickel hydrogenation catalyst. J Am Chem Soc
85(7):1005–1006. https://doi.org/10.1021/ja00890a041
90. Brown HC, Brown CA (1966) Catalytic hydrogenation—I: the reaction of platinum metal
salts with sodium borohydride—new active platinum metal catalysts for hydrogenation.
Tetrahedron 22, Supplement 8(0):149–164. http://dx.doi.org/10.1016/S0040-4020(01)821
80-3
91. Brown CA (1970) The hydrogenation of hex-1-yne over borohydride-reduced catalysts.
Evidence concerning the mechanism of reduction. J Chem Soc D Chem Commun 3:139–140.
https://doi.org/10.1039/c29700000139
92. Albani D, Karajovic K, Tata B, Li Q, Mitchell S, Lopez N, Perez-Ramirez J (2019)
Ensemble design in nickel phosphide catalysts for alkyne semi-hydrogenation. ChemCatChem
11(1):457–464. https://doi.org/10.1002/cctc.201801430
93. Zhao M (2016) Fabrication of ultrafine palladium phosphide nanoparticles as highly active
catalyst for chemoselective hydrogenation of alkynes. Chem Asian J 11(4):461–464. https://
doi.org/10.1002/asia.201500939
94. Zhao M, Ji Y, Wang M, Zhong N, Kang Z, Asao N, Jiang W-J, Chen Q (2017) Compositiondependent morphology of bi- and trimetallic phosphides: construction of amorphous Pd–
Cu–Ni–P nanoparticles as a selective and versatile catalyst. ACS Appl Mater Interfaces
9(40):34804–34811. https://doi.org/10.1021/acsami.7b08082