ACS Catalysis
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All manipulations were carried out, using conventional inert atꢀ
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mosphere gloveꢀbox and Schlenk techniques. Solvents were dried
by Grubbsꢀtype columns, except for THF which was distilled
from a sodium benzophenone ketyl solution. NMR spectra were
obtained with Bruker DPXꢀ400 and Brucker DPXꢀ600 instruꢀ
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(a) Wang, J.; SánchezꢀRoselló, M.; Aceña, J. L.; del Pozo, C.; Soꢀ
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ments ( H: 400 and 600 MHz; C: 100.6 and 151 MHz. C D6
6
were purchased from Cambridge Isotope Laboratories, and were
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dried over sodium, potassium or CaH as appropriate, distilled
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under reduced pressure and stored in ampoules with a Teflon
valve. NMR samples were prepared in New Era tubes equipped
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with J. Youngꢀtype Teflon valves. H and C NMR spectra were
referenced internally to residual protiosolvent (1H) or solvent
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(
(
13C) resonances and are reported relative to tetramethylsilane
δ=0 ppm). Chemical shifts are quoted in δ[ppm], and coupling
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39ꢀ642.
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Neumann, C. N.; Ritter, T. Angew. Chem. Int. Ed. 2015, 54, 3216 –
3221.
constants in Hertz. IR spectra were recorded by using a Perkiꢀ
nElmer 1600 FTIR spectrometer as Nujol mulls between NaCl
windows. All chemicals were purchased from Sigma– Aldrich and
Alfa Aesar and were used without further purification.
(a) Ahrens, T.; Kohlmann, J.; Ahrens, M.; Braun, T.; Chem. Rev. 2015,
1
15, 931ꢀ972. (b) Kuehnel, M. F. Lentz, D.; Braun, T.; Angew. Chem.,
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Catal. 2014, 4, 3152. (d) Amii, H.; Uneyama, K. Chem. Rev. 2009,
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7
Cp*(IMes)RuCl
Cp(IMes)Ru(pyr) ,
and
Cp*(IPr)RuCl were characterized.
+
+
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09, 2119ꢀ2183. (e) Hu, J.ꢀY.; Zhang, J.ꢀL. Top. Organomet. Chem.,
015, 52, 143ꢀ196
Cp(IPr)Ru(pyr) ,
Cp(IPr)RuH3
(1),
2
2
Cp(PPh )RuH (10), Cp(PiPr )RuH (11), Cp(IPr)RuH SiH Ph,
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(a) Aizenberg, M.; Milstein, D. Science, 1994, 265, 359ꢀ361. (b) Vela,
Cp(IPr)RuH SiHMePh, Cp(IPr)RuH SiMeCl were reported in
2
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J.; Smith, J. M.; Yu, Y.; Ketterer, N. A.; Flaschenriem, C. J.;
Lachicotte, R. J.; Holland, P. L. J. Am. Chem. Soc., 2005, 127, 7857.
our previous study. Newly synthesized compounds for this study
were characterized by NMR, IR and elemental analysis including
(
c) Peterson, A. A.; McNeill, K. Organometallics, 2006, 25, 4938. (d)
Braun, T.; Wehmeier, F.; Altenhoener, K. Angew. Chem., Int. Ed. 2007,
6, 5321ꢀ5324. (e) Reade, S. P.; Mahon, M. F.; Whittlesey, M. K. J.
of Cp*(IPr)RuH (7), Cp(IMes)RuH (8) and Cp*(IMes)RuH (9).
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Am. Chem. Soc. 2009, 131, 1847−1861. (f) Luehmann, N.; Panisch, R.;
Müller, T. Appl. Organomet. Chem. 2010, 24, 533ꢀ537. (g) Barriosꢀ
Francisco, R.; BenitezꢀPaez, T.; FloresꢀAlamo, M.; Arevalo, A.; Garꢀ
cia, J. J. Chem. - Asian J. 2011, 6, 842. (h) Ahrens, M.; Scholz, G.;
Braun, T.; Kemnitz, E. Angew. Chem., Int. Ed. 2013, 52, 5328ꢀ5332. (i)
Chen, Z.; He, C.ꢀY.; Yin, Z.; Chen, L.; He, Y.; Zhang, X. Angew.
Chem., Int. Ed. 2013, 52, 5813ꢀ5817. (j) Schwartsburd, L.; Mahon, M.
F.; Poulten, R. C.; Warren, M. R.; Whittlesey, M. K. Organometallics,
ASSOCIATED CONTENT
Supporting Information
Preparation of complexes, details of catalytic and kinetic studies.
This material is available free of charge via the Internet at
http://pubs.acs.org.
2
014, 33, 6165–6170. (k) Yamada, T.; Saito, K.; Akiyama, T. Adv.
Synth. Catal. 2016, 358, 62ꢀ66.
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(a) Douvris, C.; Ozerov, O. V. Science 2008, 321, 1188–1190. (b)
Caputo, C. B.; Stephan, D. W. Organometallics 2012, 31, 27ꢀ30. (c)
Caputo, C. B.; Hounjet, L. J.; Dobrovetsky, R.; Stephan, D. W. Science
AUTHOR INFORMATION
Corresponding Author
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013, 341, 1374ꢀ1377. (d) Zhu, J.; Perez, M.; Caputo, C. B.; Stephan,
D. W. Angew. Chem., Int. Ed. 2016, 55, 1417ꢀ1421.
Schaub, T.; Backes, M.; Radius, U. J. Am. Chem. Soc.2006, 128,
15964ꢀ15965.
Arevalo, A.; TlahuextꢀAca, A.; FloresꢀAlamo, M.; Garcia, J. J. J. Am.
Chem. Soc. 2014, 136, 4634.
*
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350. Fax: +1 (905) 682ꢀ9020.
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Notes
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(
a) Baumgartner, R.; McNeill, K. Environ Sci Technol 2012, 46, 10199.
(b) Baumgartner, R.; Stieger, G. K.; McNeill, K. Environ Sci Technol
013, 47, 6545–6553. (c) Braun, T.; Noveski, D.; Ahijado, M.;
The authors declare no competing financial interests.
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ACKNOWLEDGMENT
Wehmeier, F. Dalton Trans. 2007, 3820ꢀ3825. (d) Stanger, K. J.; Anꢀ
gelici, R. J. J. Mol. Catal. A: Chem. 2004, 207, 59ꢀ68. (e) Yang, H.;
Gao, H. R.; Angelici, R. J. Organometallics 1999, 18, 2285ꢀ2287. (f)
Young, R. J.; Grushin, V. V. Organometallics 1999, 18, 294.
Wang, D.; Astruc, D. Chem. Rev. 2015, 115, 6621−6686.
For the use of sodium formate as the hydrogen source, see: Li, J.;
Zheng, T.; Sun, H.; Li, X. Dalton Trans. 2013, 42, 13048−13053.
Kuhl, S.; Schneider, R.; Fort, Y. Adv. Synth. Catal. 2003, 345,
341−344.
We are grateful to NSERC for financial support (a DG grant to
GIN and a QEII fellowship to HVM).
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