Journal of the American Chemical Society
Page 4 of 5
Dedicated to Professor Teruaki Mukaiyama in celebration of his
90 birthday (Sotsuju). Financial support by FCI (J.B.E.), DFG
(15) Cao, Z.; Kim, D.; Hong, D.; Yu, Y.; Xu, J.; Lin, S.; Wen, X.;
Nichols, E. M.; Jeong, K.; Reimer, J. A.; Yang, P.; Chang, C. J. J. Am.
Chem. Soc. 2016, 138, 8120.
th
1
2
3
4
5
6
7
8
9
1
1
1
1
1
1
1
1
1
1
2
2
2
2
2
2
2
2
2
2
3
3
3
3
3
3
3
3
3
3
4
4
4
4
4
4
4
4
4
4
5
5
5
5
5
5
5
5
5
5
6
(Leibniz Award and SFB858), JSPS Funding Program for Next
Generation World-Leading Researchers (GR090), MEXT/JSPS
KAKENHI Grants No. 26620043 and JP16H06512 (Coordination
Asymmetry), and JSPS Core-to-Core Program "Elements Func-
tion for Transformative Catalysis and Materials" are gratefully
acknowledged. XPS measurements were conducted at Nagoya
University Nanofabrication Platform. TEM measurements were
conducted at High Voltage Electron Microscope Laboratory,
Institute of Materials and Systems for Sustainability, Nagoya
University, supported by "Nanotechnology Platform" of MEXT,
Japan. We thank M. Holtkamp for TXRF measurements.
(
16) Chen, G.; Xu, C.; Huang, X.; Ye, J.; Gu, L.; Li, G.; Tang, Z.; Wu,
B.; Yang, H.; Zhao, Z.; Zhou, Z.; Fu, G.; Zheng, N. Nat. Mater. 2016, 15,
564.
(
17) Chen, K.; Wu, H.; Hua, Q.; Chang, S.; Huang, W. Phys. Chem.
Chem. Phys. 2013, 15, 2273.
(18) Jin, L.; Liu, B.; Duay, S. S.; He, J. Catalysts 2017, 7, 44.
(19) Popov, A.; Kondratieva, E.; Goupil, J. M.; Mariey, L.; Bazin, P.;
ꢍilson, ꢎ.-P.ꢃ ꢏravert, ꢆ.ꢃ ꢐaugꢑ, F. J. Phys. Chem. C 2010, 114, 15661.
(
20) For the donor ability of NHCs in coordination chemistry see: Nel-
son, D. J.; Nolan S. P. Chem. Soc. Rev. 2013, 42, 6723.
21) a) Perdew, J. P.; Burke, K.; Ernzerhof, M. Phys. Rev. Lett. 1996,
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
(
77, 3865; b) Weigend, F.; Ahlrichs, R. Phys. Chem. Chem. Phys. 2005, 7,
3297.
(
(
REFERENCES
22) Yin, L.; Liebscher, J. Chem. Rev. 2007, 107, 133.
23) For Ni/C see: Lipshutz, B. H.; Ueda, H. Angew. Chem. Int. Ed.
(
1) a) Hopkinson, M. N.; Richter, C.; Schedler, M.; Glorius, F. Nature
2
000, 39, 4492.
2
6
014, 510, 485. b) Dröge, T.; Glorius, F. Angew. Chem. Int. Ed. 2010, 49,
940.
(24) Ruiz-Castillo, P.; Buchwald, S. L. Chem. Rev. 2016, 116, 12564.
(
Information.
(
Finke, R. G. J. Mol. Catal. A 2003, 198, 317; c) Phan, N. T. S.; Van Der
Sluys, M.; Jones, C. W. Adv. Synth. Catal. 2006, 348, 609.
(
25) For experimental details and recycling experiments see Supporting
(2) a) Kantchev, E. A. B.; O'Brien, C. J.; Organ, M. G. Angew. Chem.
Int. Ed. 2007, 46, 2768. b) Fortman, G. C.; Nolan, S. P. Chem. Soc. Rev.
011, 40, 5151.
26) a) Crabtree, R. H. Chem. Rev. 2012, 112, 1536; b) Widegren, J. A.;
2
(
(
3) Vougioukalakis, G. C.; Grubbs, R. H. Chem. Rev. 2010, 110, 1746.
4) Zhukhovitskiy, A. V.; MacLeod, M. J.; Johnson, J. A. Chem. Rev.
27) Holtkamp, M.; Wehe, C. A.; Blaske, F.; Holtschulte C.; Sperling,
2015, 115, 11503.
5) a) Weidner, T.; Baio, J. E.; Mundstock, A.; Grosse, C.; Karthauser,
M.; Karst, U. J. Anal. At. Spectrom. 2012, 27, 1799.
(
S.; Bruhn, C.; Siemeling, U. Aust. J. Chem. 2011, 64, 1177; b)
Zhukhovitskiy, A. V.; Mavros, M. G.; Van Voorhis, T.; Johnson, J. A. J.
Am. Chem. Soc. 2013, 135, 7418; c) Crudden, C. M.; Horton, J. H.;
Ebralidze, I. I.; Zenkina, O. V.; McLean, A. B.; Drevniok, B.; She, Z.;
Kraatz, H. B.; Mosey, N. J.; Seki, T.; Keske, E. C.; Leake, J. D.; Rousina-
Webb, A.; Wu, G. Nat. Chem. 2014, 6, 409; d) Wang, G.; Rühling, A.;
Amirjalayer, S.; Knor, M.; Ernst, J. B.; Richter, C.; Gao, H.-J.; Timmer,
A.; Gao, H.-Y.; Doltsinis, N. L.; Glorius, F.; Fuchs, H. Nat. Chem. 2017,
9, 152; e) Crudden, C. M.; Horton, J. H.; Narouz, M. R.; Li, Z.; Smith, C.
A.; Munro, K.; Baddeley, C. J.; Larrea, C. R.; Drevniok, B.;
Thanabalasingam, B.; McLean, A. B.; Zenkina, O. V.; Ebralidze, I. I.;
She, Z.; Kraatz, H.-B.; Mosey, N. J.; Saunders, L. N.; Yagi, A. Nat.
Commun. 2016, 7, doi: 10.1038/ncomms12654; f) Wu, C.-Y.; Wolf, W. J.;
Levartovsky, Y.; Bechtel, H. A.; Martin, M. C.; Toste, F. D.; Gross, E.
Nature 2017, 541, 511.
(
6) Hurst, E. C.; Wilson, K.; Fairlamb, I. J. S.; Chechik, V. New J.
Chem. 2009, 33, 1837.
(7) Vignolle, J.; Tilley, T. D. Chem. Commun. 2009, 7230.
(
8) a) Ranganath, K. V. S.; Kloesges, J.; Schäfer, A. H.; Glorius, F.
Angew. Chem. Int. Ed. 2010, 49, 7786; b) Ernst, J. B.; Muratsugu, S.; Fei,
W.; Tada, M.; Glorius, F. J. Am. Chem. Soc. 2016, 138, 10718
(
9) a) Richter, C.; Schaepe, K.; Glorius, F.; Ravoo, B. J. Chem.
Commun. 2014, 50, 3204; b) Ferry, A.; Schaepe, K.; Tegeder, P.; Richter,
C.; Chepiga, K. M.; Ravoo, B. J.; Glorius, F. ACS Catal. 2015, 5, ꢀꢁꢂꢁꢃ c)
ꢄꢅhling, ꢆ.ꢃ Schaeꢇe, ꢈ.ꢃ ꢄaꢉers, ꢊ.ꢃ ꢋonhꢌren, B.; Tegeder, P.; Ravoo,
B. J.; Glorius, F. Angew. Chem. Int. Ed. 2016, 55, 5856.
(
10) a) Martínez-Prieto, L. M.; Ferry, A.; Rakers, L.; Richter, C.;
Lecante, P.; Philippot, K.; Chaudret, B.; Glorius, F. Chem. Commun.
016, 52, 4768; b) Lara, P.; Martínez-Prieto, L. M.; Roselló-Merino, M.;
2
Richter, C.; Glorius, F.; Conejero, S.; Philippot, K.; Chaudret, B. Nano-
Structures & Nano-Objects 2016, 6, 39.
(11) a) Lara, P.; Rivada-Wheelaghan, O.; Conejero, S.; Poteau, R.;
Philippot, K.; Chaudret, B. Angew. Chem. Int. Ed. 2011, 50, 12080; b)
Gonzalez-Galvez, D.; Lara, P.; Rivada-Wheelaghan, O.; Conejero, S.;
Chaudret, B.; Philippot, K.; van Leeuwen, P. W. N. M. Catal. Sci.
Technol. 2013, 3, 99; c) Lara, P.; Suarez, A.; Colliere, V.; Philippot, K.;
Chaudret, B. ChemCatChem 2014, 6, 87; d) Baquero, E. A.; Tricard, S.;
Flores, J. C.; de Jesus, E.; Chaudret, B. Angew. Chem. Int. Ed. 2014, 53,
1
3220.
12) a) Fedorov, A.; Liu, H.-J.; Lo, H.-K.; Copéret, C. J. Am. Chem.
(
Soc. 2016, 138, 16502; b) Salorinne, K.; Man, R. W. Y.; Li, C.-H.; Taki,
M.; Nambo, M.; Crudden, C. M. Angew. Chem. Int. Ed. 2017, 129, 6294.
(
13) MacLeod, M. J.; Johnson, J. A. J. Am. Chem. Soc. 2015, 137,
974.
14) Rodríguez-Castillo, M.; Lugo-Preciado, G.; Laurencin, D.;
7
(
Tielens, F.; van der Lee, A.; Clément, S.; Guari, Y.; López-de-Luzuriaga,
J. M.; Monge, M.; Remacle, F.; Richeter, S. Chem. Eur. J. 2016, 22,
1
0446.
ACS Paragon Plus Environment