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102. Miyamura H, Suzuki A, Yasukawa T, Kobayashi S (2018) Polysilane-immobilized Rh–Pt
bimetallic nanoparticles as powerful arene hydrogenation catalysts: synthesis, reactions under
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https://doi.org/10.1021/jacs.8b06015
103. Park JH, Kim E, Chung YK (2008) Heterobimetallic cobalt/rhodium nanoparticle-catalyzed
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104. Park KH, Jung IG, Chung YK (2004) A PausonÀKhand-type reaction between alkynes and
olefinic aldehydes catalyzed by rhodium/cobalt heterobimetallic nanoparticles: an olefinic
aldehyde as an olefin and CO source. Org Lett 6:1183–1186
105. Park JH, Chung YK (2008) Cobalt–rhodium heterobimetallic nanoparticle-catalyzed
reactions. Dalton Trans:2369–2378
106. Park JW, Chung YK (2015) Hydrogen-free cobalt–rhodium heterobimetallic nanoparticlecatalyzed reductive amination of aldehydes and ketones with amines and nitroarenes in
the presence of carbon monoxide and water. ACS Catal 5:4846–4850
107. Choi I, Chun S, Chung YK (2017) Bimetallic cobalt–rhodium nanoparticle-catalyzed
reductive amination of aldehydes with nitroarenes under atmospheric hydrogen. J Org Chem
82:12771–12777
108. Choi I, Chung H, Park JW, Chung YK (2016) Active and recyclable catalytic synthesis
of indoles by reductive cyclization of 2-(2-nitroaryl)acetonitriles in the presence of Co–Rh
Heterobimetallic nanoparticles with atmospheric hydrogen under mild conditions. Org Lett
18:5508–5511
109. Chandra D, Inoue Y, Sasase M, Kitano M, Bhaumik A, Kamata K, Hosono H, Hara M (2018)
A high performance catalyst of shape-specific ruthenium nanoparticles for production of
primary amines by reductive amination of carbonyl compounds. Chem Sci 9:5949–5956.
https://doi.org/10.1039/C8SC01197D
110. Komanoya T, Kinemura T, Kita Y, Kamata K, Hara M (2017) Electronic effect of ruthenium
nanoparticles on efficient reductive amination of carbonyl compounds. J Am Chem Soc
139:11493–11499. https://doi.org/10.1021/jacs.7b04481
128
M. Cortes-Clerget et al.
Lambert RM (2009) Evidence for heterogeneous Sonogashira coupling of phenylacetylene
and iodobenzene catalyzed by well defined rhodium nanoparticles. Dalton Trans
37:7602–7605
96. Karakulina A, Gopakumar A, Akçok I, Roulier BL, LaGrange T, Katsyuba SA, Das S,
Dyson PJ (2016) A rhodium nanoparticle–Lewis acidic ionic liquid catalyst for the
chemoselective reduction of heteroarenes. Angew Chem Int Ed 55:292–296
97. Yasukawa T, Miyamura H, Kobayashi S (2012) Polymer-incarcerated chiral Rh/Ag
nanoparticles for asymmetric 1,4-addition reactions of arylboronic acids to enones: remarkable
effects of bimetallic structure on activity and metal leaching. J Am Chem Soc
134:16963–16966
98. Yasukawa T, Suzuki A, Miyamura H, Nishino K, Kobayashi S (2015) Chiral metal
nanoparticle systems as heterogeneous catalysts beyond homogeneous metal complex
catalysts for asymmetric addition of arylboronic acids to α,β-unsaturated carbonyl compounds.
J Am Chem Soc 137:6616–6623
99. Yasukawa T, Miyamura H, Kobayashi S (2014) Chiral metal nanoparticle-catalyzed
asymmetric C–C bond formation reactions. Chem Soc Rev 43:1450–1461. https://doi.org/
10.1039/C3CS60298B
100. Yasukawa T, Miyamura H, Kobayashi S (2016) Chiral ligand-modified metal nanoparticles
as unique catalysts for asymmetric C–C bond-forming reactions: how are active species
generated? ACS Catal 6:7979–7988. https://doi.org/10.1021/acscatal.6b02446
101. Yasukawa T, Kuremoto T, Miyamura H, Kobayashi S (2016) Asymmetric arylation of imines
catalyzed by heterogeneous chiral rhodium nanoparticles. Org Lett 18:2716–2718
102. Miyamura H, Suzuki A, Yasukawa T, Kobayashi S (2018) Polysilane-immobilized Rh–Pt
bimetallic nanoparticles as powerful arene hydrogenation catalysts: synthesis, reactions under
batch and flow conditions and reaction mechanism. J Am Chem Soc 140:11325–11334.
https://doi.org/10.1021/jacs.8b06015
103. Park JH, Kim E, Chung YK (2008) Heterobimetallic cobalt/rhodium nanoparticle-catalyzed
carbonylative cycloaddition of 2-alkynylanilines to oxindoles. Org Lett 10:4719–4721
104. Park KH, Jung IG, Chung YK (2004) A PausonÀKhand-type reaction between alkynes and
olefinic aldehydes catalyzed by rhodium/cobalt heterobimetallic nanoparticles: an olefinic
aldehyde as an olefin and CO source. Org Lett 6:1183–1186
105. Park JH, Chung YK (2008) Cobalt–rhodium heterobimetallic nanoparticle-catalyzed
reactions. Dalton Trans:2369–2378
106. Park JW, Chung YK (2015) Hydrogen-free cobalt–rhodium heterobimetallic nanoparticlecatalyzed reductive amination of aldehydes and ketones with amines and nitroarenes in
the presence of carbon monoxide and water. ACS Catal 5:4846–4850
107. Choi I, Chun S, Chung YK (2017) Bimetallic cobalt–rhodium nanoparticle-catalyzed
reductive amination of aldehydes with nitroarenes under atmospheric hydrogen. J Org Chem
82:12771–12777
108. Choi I, Chung H, Park JW, Chung YK (2016) Active and recyclable catalytic synthesis
of indoles by reductive cyclization of 2-(2-nitroaryl)acetonitriles in the presence of Co–Rh
Heterobimetallic nanoparticles with atmospheric hydrogen under mild conditions. Org Lett
18:5508–5511
109. Chandra D, Inoue Y, Sasase M, Kitano M, Bhaumik A, Kamata K, Hosono H, Hara M (2018)
A high performance catalyst of shape-specific ruthenium nanoparticles for production of
primary amines by reductive amination of carbonyl compounds. Chem Sci 9:5949–5956.
https://doi.org/10.1039/C8SC01197D
110. Komanoya T, Kinemura T, Kita Y, Kamata K, Hara M (2017) Electronic effect of ruthenium
nanoparticles on efficient reductive amination of carbonyl compounds. J Am Chem Soc
139:11493–11499. https://doi.org/10.1021/jacs.7b04481
128
M. Cortes-Clerget et al.