302
A. Palazzolo et al.
51. Yu PR, Hesk D, Rivera N, Pelczer I, Chirik PJ (2016) Nature. Nature Publishing Group vol
529, pp 195–199
52. Palmer WN, Chirik PJ (2017) Cobalt-catalyzed stereoretentive hydrogen isotope exchange of
C(sp3)-H bonds. ACS Catal 7:5674–5678
53. Yang H, Zarate C, Palmer WN, Rivera N, Hesk D, Chirik PJ (2018) Site-selective nickelcatalyzed hydrogen isotope exchange in N-heterocycles and Its application to the tritiation of
pharmaceuticals. ACS Catal 8:10210–10218
54. Zarate C, Yang H, Bezdek MJ, Hesk D, Chirik PJ (2019) Ni(I)-X complexes bearing a bulky αdiimine ligand: synthesis, structure, and superior catalytic performance in the hydrogen isotope
exchange in pharmaceuticals. J Am Chem Soc 141:5034–5044
55. Pla D, Gomez M (2016) Metal and metal oxide nanoparticles: a lever for C-H functionalization.
ACS Catal 6:3537–3552
56. Ott LS, Cline ML, Deetlefs M, Seddon KR, Finke RG (2005) Nanoclusters in ionic liquids:
evidence for N-Heterocyclic carbene formation from imidazolium-based ionic liquids detected
by 2 H NMR. J Am Chem Soc 127:5758–5759
57. Sullivan JA, Flanagan KA, Hain H (2008) Selective H-D exchange catalyzed by aqueous phase
and immobilized Pd nanoparticles. Catal Today 139:154–160
58. Guy KA, Shapley JR (2009) H-D exchange between N-heterocyclic compounds and D 2 O with
a Pd/PVP colloid catalyst. Organometallics 28:4020–4027
59. Pan C, Pelzer K, Philippot K, Chaudret B, Dassenoy F, Lecante P, Casanove M-J (2001) Ligandstabilized ruthenium nanoparticles: synthesis, organization, and dynamics. J Am Chem Soc
123:7584–7593
60. Pery T, Pelzer K, Buntkowsky G, Philippot K, Limbach H-H, Chaudret B (2005) Direct NMR
evidence for the presence of mobile surface hydrides on ruthenium nanoparticles. Chem Phys
Chem 6:605–607
61. Breso-Femenia E, Godard C, Claver C, Chaudret B, Castillón S (2015) Selective catalytic
deuteration of phosphorus ligands using ruthenium nanoparticles: a new approach to gain
information on ligand coordination. Chem Commun 51:16342–16345
62. Pieters G, Taglang C, Bonnefille E, Gutmann T, Puente C, Berthet J-C, Dugave C, Chaudret B,
Rousseau B (2014) Regioselective and stereospecific deuteration of bioactive aza compounds
by the use of ruthenium nanoparticles. Angew Chem Int Ed 53:230–234
63. Taglang C, Martinez-Prieto LM, del Rosal I, Maron L, Poteau R, Philippot K, Chaudret B,
Perato S, Sam Lone A, Puente C et al. (2015) Enantiospecific C-H activation using ruthenium
nanocatalysts. Angew Chem Int Ed 54:10474–10477
64. Martínez-Prieto LM, Baquero EA, Pieters G, Flores JC, de Jesús E, Nayral C, Delpech F,
van Leeuwen PWNM, Lippens G, Chaudret B (2017) Monitoring of nanoparticle reactivity
in solution: interaction of l-lysine and Ru nanoparticles probed by chemical shift perturbation
parallels regioselective H/D exchange. Chem Commun 53:5850–5853
65. Bhatia S, Spahlinger G, Boukhumseen N, Boll Q, Li Z, Jackson JE (2016) Stereoretentive H/D
exchange via an electroactivated heterogeneous catalyst at sp 3 C-H sites bearing amines or
alcohols. Eur J Org Chem 2016:4230–4235
66. Bouzouita D, Lippens G, Baquero EA, Fazzini PF, Pieters G, Coppel Y, Lecante P, Tricard S,
Martinez-Prieto LM, Chaudret B (2019) Tuning the catalytic activity and selectivity of watersoluble bimetallic RuPt nanoparticles by modifying their surface metal distribution. Nanoscale
11:16544–16552
67. Palazzolo A, Feuillastre S, Pfeifer V, Garcia-Argote S, Bouzouita D, Tricard S, Chollet C,
Marcon E, Buisson D-A, Cholet S et al. (2019) Efficient access to deuterated and tritiated
nucleobase pharmaceuticals and oligonucleotides using hydrogen-isotope exchange. Angew
Chem Int Ed 58:4891–4895
68. Rothermel N, Bouzouita D, Roether T, de Rosal I, Tricard S, Poteau R, Gutmann T, Chaudret B,
Limbach H-H, Buntkowsky G (2018) Surprising differences of alkane C-H activation catalyzed
by ruthenium nanoparticles: complex surface-substrate recognition? Chem Cat Chem 10:4243–
4247
A. Palazzolo et al.
51. Yu PR, Hesk D, Rivera N, Pelczer I, Chirik PJ (2016) Nature. Nature Publishing Group vol
529, pp 195–199
52. Palmer WN, Chirik PJ (2017) Cobalt-catalyzed stereoretentive hydrogen isotope exchange of
C(sp3)-H bonds. ACS Catal 7:5674–5678
53. Yang H, Zarate C, Palmer WN, Rivera N, Hesk D, Chirik PJ (2018) Site-selective nickelcatalyzed hydrogen isotope exchange in N-heterocycles and Its application to the tritiation of
pharmaceuticals. ACS Catal 8:10210–10218
54. Zarate C, Yang H, Bezdek MJ, Hesk D, Chirik PJ (2019) Ni(I)-X complexes bearing a bulky αdiimine ligand: synthesis, structure, and superior catalytic performance in the hydrogen isotope
exchange in pharmaceuticals. J Am Chem Soc 141:5034–5044
55. Pla D, Gomez M (2016) Metal and metal oxide nanoparticles: a lever for C-H functionalization.
ACS Catal 6:3537–3552
56. Ott LS, Cline ML, Deetlefs M, Seddon KR, Finke RG (2005) Nanoclusters in ionic liquids:
evidence for N-Heterocyclic carbene formation from imidazolium-based ionic liquids detected
by 2 H NMR. J Am Chem Soc 127:5758–5759
57. Sullivan JA, Flanagan KA, Hain H (2008) Selective H-D exchange catalyzed by aqueous phase
and immobilized Pd nanoparticles. Catal Today 139:154–160
58. Guy KA, Shapley JR (2009) H-D exchange between N-heterocyclic compounds and D 2 O with
a Pd/PVP colloid catalyst. Organometallics 28:4020–4027
59. Pan C, Pelzer K, Philippot K, Chaudret B, Dassenoy F, Lecante P, Casanove M-J (2001) Ligandstabilized ruthenium nanoparticles: synthesis, organization, and dynamics. J Am Chem Soc
123:7584–7593
60. Pery T, Pelzer K, Buntkowsky G, Philippot K, Limbach H-H, Chaudret B (2005) Direct NMR
evidence for the presence of mobile surface hydrides on ruthenium nanoparticles. Chem Phys
Chem 6:605–607
61. Breso-Femenia E, Godard C, Claver C, Chaudret B, Castillón S (2015) Selective catalytic
deuteration of phosphorus ligands using ruthenium nanoparticles: a new approach to gain
information on ligand coordination. Chem Commun 51:16342–16345
62. Pieters G, Taglang C, Bonnefille E, Gutmann T, Puente C, Berthet J-C, Dugave C, Chaudret B,
Rousseau B (2014) Regioselective and stereospecific deuteration of bioactive aza compounds
by the use of ruthenium nanoparticles. Angew Chem Int Ed 53:230–234
63. Taglang C, Martinez-Prieto LM, del Rosal I, Maron L, Poteau R, Philippot K, Chaudret B,
Perato S, Sam Lone A, Puente C et al. (2015) Enantiospecific C-H activation using ruthenium
nanocatalysts. Angew Chem Int Ed 54:10474–10477
64. Martínez-Prieto LM, Baquero EA, Pieters G, Flores JC, de Jesús E, Nayral C, Delpech F,
van Leeuwen PWNM, Lippens G, Chaudret B (2017) Monitoring of nanoparticle reactivity
in solution: interaction of l-lysine and Ru nanoparticles probed by chemical shift perturbation
parallels regioselective H/D exchange. Chem Commun 53:5850–5853
65. Bhatia S, Spahlinger G, Boukhumseen N, Boll Q, Li Z, Jackson JE (2016) Stereoretentive H/D
exchange via an electroactivated heterogeneous catalyst at sp 3 C-H sites bearing amines or
alcohols. Eur J Org Chem 2016:4230–4235
66. Bouzouita D, Lippens G, Baquero EA, Fazzini PF, Pieters G, Coppel Y, Lecante P, Tricard S,
Martinez-Prieto LM, Chaudret B (2019) Tuning the catalytic activity and selectivity of watersoluble bimetallic RuPt nanoparticles by modifying their surface metal distribution. Nanoscale
11:16544–16552
67. Palazzolo A, Feuillastre S, Pfeifer V, Garcia-Argote S, Bouzouita D, Tricard S, Chollet C,
Marcon E, Buisson D-A, Cholet S et al. (2019) Efficient access to deuterated and tritiated
nucleobase pharmaceuticals and oligonucleotides using hydrogen-isotope exchange. Angew
Chem Int Ed 58:4891–4895
68. Rothermel N, Bouzouita D, Roether T, de Rosal I, Tricard S, Poteau R, Gutmann T, Chaudret B,
Limbach H-H, Buntkowsky G (2018) Surprising differences of alkane C-H activation catalyzed
by ruthenium nanoparticles: complex surface-substrate recognition? Chem Cat Chem 10:4243–
4247