10 Progress in the Selective Semi-hydrogenation of Alkynes …
343
145. López N, Bridier B, Pérez-Ramírez J (2008) Discriminating reasons for selectivity enhancement of CO in alkyne hydrogenation on palladium. J Phys Chem C 112(25):9346–9350.
https://doi.org/10.1021/jp711258q
146. Uzio D, Berhault G (2010) Factors governing the catalytic reactivity of metallic nanoparticles.
Catal Rev 52(1):106–131. https://doi.org/10.1080/01614940903510496
147. Corma A, Serna P, Concepción P, Calvino JJ (2008) Transforming nonselective into chemoselective metal catalysts for the hydrogenation of substituted nitroaromatics. J Am Chem Soc
130(27):8748–8753. https://doi.org/10.1021/ja800959g
148. Moreno-Castilla C, Ferro-Garcia MA, Joly JP, Bautista-Toledo I, Carrasco-Marin F, RiveraUtrilla J (1995) Activated carbon surface modifications by nitric acid, hydrogen peroxide,
and ammonium peroxydisulfate treatments. Langmuir 11(11):4386–4392. https://doi.org/10.
1021/la00011a035
149. Semagina N, Grasemann M, Xanthopoulos N, Renken A, Kiwi-Minsker L (2007) Structured
catalyst of Pd/ZnO on sintered metal fibers for 2-methyl-3-butyn-2-ol selective hydrogenation.
J Catal 251(1):213–222. https://doi.org/10.1016/j.jcat.2007.06.028
150. Mao S, Zhao B, Wang Z, Gong Y, Lü G, Ma X, Yu L, Wang Y (2019) Tuning the catalytic
performance for the semi-hydrogenation of alkynols by selectively poisoning the active sites
of Pd catalysts. Green Chem 21(15):4143–4151. https://doi.org/10.1039/C9GC01356C
151. Easterday R, Leonard C, Sanchez-Felix O, Losovyj Y, Pink M, Stein BD, Morgan DG,
Lyubimova NA, Nikoshvili LZ, Sulman EM, Mahmoud WE, Al-Ghamdi AA, Bronstein
LM (2014) Fabrication of magnetically recoverable catalysts based on mixtures of Pd and
iron oxide nanoparticles for hydrogenation of alkyne alcohols. ACS Appl Mater Interfaces
6(23):21652–21660. https://doi.org/10.1021/am5067223
152. Uberman PM, Costa NJS, Philippot K, C. Carmona R, Dos Santos AA, Rossi LM (2014) A
recoverable Pd nanocatalyst for selective semi-hydrogenation of alkynes: hydrogenation of
benzyl-propargylamines as a challenging model. Green Chem 16(10):4566–4574. http://dx.
doi.org/10.1039/c4gc00669k
153. Tejeda-Serrano M, Cabrero-Antonino JR, Mainar-Ruiz V, Lopez-Haro M, Hernandez-Garrido
JC, Calvino JJ, Leyva-Perez A, Corma A (2017) Synthesis of supported planar iron oxide
nanoparticles and their chemo- and stereoselectivity for hydrogenation of alkynes. ACS Catal
7(5):3721–3729. https://doi.org/10.1021/acscatal.7b00037
154. Ruiz Puigdollers A, Schlexer P, Tosoni S, Pacchioni G (2017) Increasing oxide reducibility: the
role of metal/oxide interfaces in the formation of oxygen vacancies. ACS Catal 7(10):6493–
6513. https://doi.org/10.1021/acscatal.7b01913
155. Schlexer P, Ruiz Puigdollers A, Pacchioni G (2019) Role of metal/oxide interfaces in
enhancing the local oxide reducibility. Top Catal 62(17):1192–1201. https://doi.org/10.1007/
s11244-018-1056-5
156. Yang S, Cao C, Peng L, Zhang J, Han B, Song W (2016) A Pd-Cu 2 O nanocomposite as an
effective synergistic catalyst for selective semi-hydrogenation of the terminal alkynes only.
Chem Commun 52(18):3627–3630. https://doi.org/10.1039/c6cc00143b
157. Liu K, Qin R, Zhou L, Liu P, Zhang Q, Jing W, Ruan P, Gu L, Fu G, Zheng N (2019)
Cu 2 O-supported atomically dispersed Pd catalysts for semihydrogenation of terminal alkynes:
critical role of oxide supports. CCS Chemistry 1(2):207–214. https://doi.org/10.31635/ccs
chem.019.20190008
158. Mitsudome T, Yamamoto M, Maeno Z, Mizugaki T, Jitsukawa K, Kaneda K (2015) One-step
synthesis of core-gold/shell-ceria nanomaterial and its catalysis for highly selective semihydrogenation of alkynes. J Am Chem Soc 137(42):13452–13455. https://doi.org/10.1021/jacs.
5b07521
159. Wang M-M, He L, Liu Y-M, Cao Y, He H-Y, Fan K-N (2011) Gold supported on
mesostructured ceria as an efficient catalyst for the chemoselective hydrogenation of carbonyl
compounds in neat water. Green Chem 13(3):602–607. https://doi.org/10.1039/C0GC00937G
160. Shao L, Huang X, Teschner D, Zhang W (2014) Gold supported on graphene oxide: an active
and selective catalyst for phenylacetylene hydrogenations at low temperatures. ACS Catal
4(7):2369–2373. https://doi.org/10.1021/cs5002724
343
145. López N, Bridier B, Pérez-Ramírez J (2008) Discriminating reasons for selectivity enhancement of CO in alkyne hydrogenation on palladium. J Phys Chem C 112(25):9346–9350.
https://doi.org/10.1021/jp711258q
146. Uzio D, Berhault G (2010) Factors governing the catalytic reactivity of metallic nanoparticles.
Catal Rev 52(1):106–131. https://doi.org/10.1080/01614940903510496
147. Corma A, Serna P, Concepción P, Calvino JJ (2008) Transforming nonselective into chemoselective metal catalysts for the hydrogenation of substituted nitroaromatics. J Am Chem Soc
130(27):8748–8753. https://doi.org/10.1021/ja800959g
148. Moreno-Castilla C, Ferro-Garcia MA, Joly JP, Bautista-Toledo I, Carrasco-Marin F, RiveraUtrilla J (1995) Activated carbon surface modifications by nitric acid, hydrogen peroxide,
and ammonium peroxydisulfate treatments. Langmuir 11(11):4386–4392. https://doi.org/10.
1021/la00011a035
149. Semagina N, Grasemann M, Xanthopoulos N, Renken A, Kiwi-Minsker L (2007) Structured
catalyst of Pd/ZnO on sintered metal fibers for 2-methyl-3-butyn-2-ol selective hydrogenation.
J Catal 251(1):213–222. https://doi.org/10.1016/j.jcat.2007.06.028
150. Mao S, Zhao B, Wang Z, Gong Y, Lü G, Ma X, Yu L, Wang Y (2019) Tuning the catalytic
performance for the semi-hydrogenation of alkynols by selectively poisoning the active sites
of Pd catalysts. Green Chem 21(15):4143–4151. https://doi.org/10.1039/C9GC01356C
151. Easterday R, Leonard C, Sanchez-Felix O, Losovyj Y, Pink M, Stein BD, Morgan DG,
Lyubimova NA, Nikoshvili LZ, Sulman EM, Mahmoud WE, Al-Ghamdi AA, Bronstein
LM (2014) Fabrication of magnetically recoverable catalysts based on mixtures of Pd and
iron oxide nanoparticles for hydrogenation of alkyne alcohols. ACS Appl Mater Interfaces
6(23):21652–21660. https://doi.org/10.1021/am5067223
152. Uberman PM, Costa NJS, Philippot K, C. Carmona R, Dos Santos AA, Rossi LM (2014) A
recoverable Pd nanocatalyst for selective semi-hydrogenation of alkynes: hydrogenation of
benzyl-propargylamines as a challenging model. Green Chem 16(10):4566–4574. http://dx.
doi.org/10.1039/c4gc00669k
153. Tejeda-Serrano M, Cabrero-Antonino JR, Mainar-Ruiz V, Lopez-Haro M, Hernandez-Garrido
JC, Calvino JJ, Leyva-Perez A, Corma A (2017) Synthesis of supported planar iron oxide
nanoparticles and their chemo- and stereoselectivity for hydrogenation of alkynes. ACS Catal
7(5):3721–3729. https://doi.org/10.1021/acscatal.7b00037
154. Ruiz Puigdollers A, Schlexer P, Tosoni S, Pacchioni G (2017) Increasing oxide reducibility: the
role of metal/oxide interfaces in the formation of oxygen vacancies. ACS Catal 7(10):6493–
6513. https://doi.org/10.1021/acscatal.7b01913
155. Schlexer P, Ruiz Puigdollers A, Pacchioni G (2019) Role of metal/oxide interfaces in
enhancing the local oxide reducibility. Top Catal 62(17):1192–1201. https://doi.org/10.1007/
s11244-018-1056-5
156. Yang S, Cao C, Peng L, Zhang J, Han B, Song W (2016) A Pd-Cu 2 O nanocomposite as an
effective synergistic catalyst for selective semi-hydrogenation of the terminal alkynes only.
Chem Commun 52(18):3627–3630. https://doi.org/10.1039/c6cc00143b
157. Liu K, Qin R, Zhou L, Liu P, Zhang Q, Jing W, Ruan P, Gu L, Fu G, Zheng N (2019)
Cu 2 O-supported atomically dispersed Pd catalysts for semihydrogenation of terminal alkynes:
critical role of oxide supports. CCS Chemistry 1(2):207–214. https://doi.org/10.31635/ccs
chem.019.20190008
158. Mitsudome T, Yamamoto M, Maeno Z, Mizugaki T, Jitsukawa K, Kaneda K (2015) One-step
synthesis of core-gold/shell-ceria nanomaterial and its catalysis for highly selective semihydrogenation of alkynes. J Am Chem Soc 137(42):13452–13455. https://doi.org/10.1021/jacs.
5b07521
159. Wang M-M, He L, Liu Y-M, Cao Y, He H-Y, Fan K-N (2011) Gold supported on
mesostructured ceria as an efficient catalyst for the chemoselective hydrogenation of carbonyl
compounds in neat water. Green Chem 13(3):602–607. https://doi.org/10.1039/C0GC00937G
160. Shao L, Huang X, Teschner D, Zhang W (2014) Gold supported on graphene oxide: an active
and selective catalyst for phenylacetylene hydrogenations at low temperatures. ACS Catal
4(7):2369–2373. https://doi.org/10.1021/cs5002724