ChemCatChem
10.1002/cctc.201601141
COMMUNICATION
T. Kobayashi, N. Sayo, T. Saito, Org. Process Res. Dev. 2012, 16, 166-
Experimental Section
171.
[
[
11]
12]
a) H. Doucet, T. Ohkuma, K. Murata, T. Yokozawa, M. Kozawa, E.
Katayama, A. F. England, T. Ikariya, R. Noyori, Angew. Chem. Int. Ed.
1998, 37, 1703-1707; b) R. Noyori, T. Ohkuma, Angew. Chem. Int. Ed.
2001, 40, 40-73; c) S. E. Clapham, A. Hadzovic, R. H. Morris, Coord.
Chem. Rev. 2004, 248, 2201-2237; d) B. Zhao, Z. Han, K. Ding, Angew.
Chem. Int. Ed. 2013, 52, 4744-4788.
Complex 1. Bis[(2-di-isopropylphosphino)ethyl]amine (0.492 mmol, 1.7
mL, 10 wt% in THF, 1.0 equiv.) was added to a solution of Re(CO)
5
Br
(0.492 mmol, 200 mg 1.0 equiv.) in toluene (8 mL). The mixture was stirred
at 100 °C for 18 h. Toluene was then evaporated. The crude residue was
then recrystallized from dichloromethane and pentane to afford white
needle crystals (297 mg, 92%). Complete details of the X-ray analyses
reported herein have been deposited at the Cambridge Crystallographic
Data Center (CCDC 1501902). Typical catalytic hydrogenation. In an
argon filled glove box, an autoclave was charged with complex 1 (8.2 mg,
a) H.-F. Lang, P. E. Fanwick, R. A. Walton, Inorg. Chim. Acta 2002, 329,
1-8; b) O. V. Ozerov, J. C. Huffman, L. A. Watson, K. G. Caulton,
Organometallics 2003, 22, 2539-2541; c) O. V. Ozerov, L. A. Watson, M.
Pink, K. G. Caulton, J. Am. Chem. Soc. 2004, 126, 6363-6378; d) O. V.
Ozerov, L. A. Watson, M. Pink, K. G. Caulton, J. Am. Chem. Soc. 2007,
0
.5 mol%) and toluene (2.5 mL), followed by ketone (2.5 mmol) and t-
BuOK (2.8 mg, 1.0 mol%), in this order. The autoclave is then charged H
30 bar). The mixture was stirred for 17 h at 70 °C in an oil bath.
129, 6003-6016; e) T. J. Korstanje, M. Lutz, J. T. B. H. Jastrzebski, R. J.
2
M. Klein Gebbink, Organometallics 2014, 33, 2201-2209; f) A. T.
Radosevich, J. G. Melnick, S. A. Stoian, D. Bacciu, C.-H. Chen, B. M.
Foxman, O. V. Ozerov, D. G. Nocera, Inorg. Chem. 2009, 48, 9214-
(
9221; g) M. Porchia, F. Tisato, F. Refosco, C. Bolzati, M. Cavazza-
Ceccato, G. Bandoli, A. Dolmella, Inorg. Chem. 2005, 44, 4766-4776; h)
F. Tisato, F. Refosco, M. Porchia, C. Bolzati, G. Bandoli, A. Dolmella, A.
Duatti, A. Boschi, C. M. Jung, H.-J. Pietzsch, W. Kraus, Inorg. Chem.
2004, 43, 8617-8625; i) C. Bolzati, F. Refosco, A. Cagnolini, F. Tisato, A.
Boschi, A. Duatti, L. Uccelli, A. Dolmella, E. Marotta, M. Tubaro, Eur. J.
Inorg. Chem. 2004, 1902-1913; j) Y.-S. Kim, Z. Hea, R. Schibli, S. Liu,
Inorg. Chim. Acta 2006, 359, 2479-2488; k) I. Klopsch, M. Kinauer, M.
Finger, C. Würtele, S. Schneider, Angew. Chem. Int. Ed. 2016, 55, 4786-
Acknowledgements ((optional))
We thank the CNRS, the Université de Rennes 1 and FEDER
founds.
Keywords: Rhenium • hydrogenation• ketones • mechanism •
4
789; l) I. Klopsch, M. Finger, C. Würtele, B. Milde, D. B. Werz, S.
DFT-D3 calculations
Schneider, J. Am. Chem. Soc. 2014, 136, 6881-6883; m) M. Vogt, A.
Nerush, Y. Diskin-Posner, Y. Ben-David, D. Milstein, Chem. Sci. 2014,
[
[
1]
2]
J. G. De Vries, C. J. Elsevier, The Handbook of Homogeneous
Hydrogenation, WILEY-VCH, Weinhem, 2007.
a) J. G. de Vries, P. J. Deuss, K. Barta, Catal. Sci. Technol. 2014, 4,
5
, 2043-2051; n) M. Vogt, A. Nerush, M. A. Iron, G. Leitus, Y. Diskin-
Posner, L. J. W. Shimon, Y. Ben-David, D. Milstein, J. Am. Chem. Soc.
013, 135, 17004-17018.
2
1174-1196; b) G. W. Huber, S. Iborra, A. Corma, Chem. Rev. 2006, 106,
[
13]
E. Alberico, P. Sponholz, C. Cordes, M. Nielsen, H.-J. Drexler, W.
Baumann, H. Junge, M. Beller, Angew. Chem. Int. Ed. 2013, 52, 14162-
4044-4098; c) C.-H. Zhou, X. Xia, C.-X. Lin, D.-S. Tong, J. Beltramini,
Chem. Soc. Rev. 2011, 40, 5588-5617; d) P. N. R. Vennestrøm, C. M.
Osmundsen, C. H. Christensen, E. Taarning, Angew. Chem. Int. Ed.
1
4166.
M. Käß, A. Friedrich, M. Drees, S. Schneider, Angew. Chem. Int. Ed.
009, 48, 905-907.
[
[
[
14]
15]
16]
2
011, 50, 10502-10509.
a) D. A. Valyaev, G. Lavigne, N. Lugan, Coord. Chem. Rev. 2016, 308,
91-235; b) Y. Kuninobu, K. Takai, Chem. Rev. 2011, 111, 1938-1953.
2
[
[
3]
4]
M. Bertoli, A. Choualeb, A. J. Lough, B. Moore, D. Spasyuk, D. G. Gusev,
Organometallics 2011, 30, 3479-3482.
a) I. T. Horváth, Green Chem. 2008, 10, 1024-1028; b) J. C. Serrano-
Ruiz, R. Luque, A. Sepúlveda-Escribano, Chem. Soc. Rev. 2011, 40,
1
S. Elangovan, C. Topf, S. Fischer, H. Jiao, A. Spannenberg, W.
Baumann, R. Ludwig, K. Junge, M. Beller, J. Am. Chem. Soc. 2016, 138,
8809-8814.
5266-5281; c) I. T. Horváth, H. Mehdi, V. Fábos, L. Boda, L. T. Mika,
[
[
5]
6]
A. Mukherjee, A. Nerush, G. Leitus, L. J. W. Shimon, Y. Ben David, N.
A. Espinosa Jalapa, D. Milstein, J. Am. Chem. Soc. 2016, 138, 4298-
Green Chem. 2008, 10, 238-242.
a) L. Deng, J. Li, D.-M. Lai, Y. Fu, Q.-X. Guo, Angew. Chem. Int. Ed.
[
[
17]
18]
4301.
2
2
009, 48, 6529-6532; b) W. Li, J.-H. Xie, H. Lin, Q.-L. Zhou, Green Chem.
012, 14, 2388-2390; c) V. Fábos, L. T. Mika, I. T. Horváth,
a) D. Baudry, M. Ephritikhine, H. Felkin, R. Holmes-Smith, J. Chem. Soc.,
Chem. Commun. 1983, 788-789; b) D. Baudry, M. Ephritikhine, H. Felkin,
J. Chem. Soc., Chem. Commun. 1980, 1243-1244.
Organometallics 2014, 33, 181-187; d) K. Osakada, T. Ikariya, S.
Yoshikawa, J. Organomet. Chem. 1982, 231, 79-90; e) F. M. A. Geilen,
B. Engendahl, A. Harwardt, W. Marquardt, J. Klankermayer, W. Leitner,
Angew. Chem. Int. Ed. 2010, 49, 5510-5514.
a) S. Chakraborty, P. O. Lagaditis, M. Förster, E. A. Bielinski, N. Hazari,
M. C. Holthausen, W. D. Jones, S. Schneider, ACS Catal. 2014, 4, 3994-
[
[
7]
8]
D. G. DeWit, K. Folting, W. E. Streib, K. G. Caulton, Organometallics
1985, 4, 1149-1153.
a) Y. Jiang, H. Berke, Chem. Commun. 2007, 3571-3573; b) A. Choualeb,
E. Maccaroni, O. Blacque, H. W. Schmalle, H. Berke, Organometallics
2008, 27, 3474-3481; c) B. Dudle, K. Rajesh, O. Blacque, H. Berke, J.
4
003; b) R. Xu, S. Chakraborty, S. M. Bellows, H. Yuan, T. R. Cundari,
W. D. Jones, ACS Catal. 2016, 6, 2127-2135; c) X. Yang, ACS Catal.
013, 3, 2684-2688.
Am. Chem. Soc. 2011, 133, 8168-8178; d) Y. Jiang, B. Schirmer, O.
Blacque, T. Fox, S. Grimme, H. Berke, J. Am. Chem. Soc. 2013, 135,
2
4088-4102; e) Y. Jiang, W. Huang, H. W. Schmalle, O. Blacque, T. Fox,
[
[
19]
20]
See S.I for computational details.
H. Berke, Organometallics 2013, 32, 7043-7052; f) A. Choualeb, A. J.
Lough, D. G. Gusev, Organometallics 2007, 26, 3509-3515; g) K. Rajesh,
B. Dudle, O. Blacque, H. Berke, Adv. Synth. Catal. 2011, 353, 1479-1484.
A. Landwehr, B. Dudle, T. Fox, O. Blacque, H. Berke, Chem. Eur. J. 2012,
Although TS-8-4 is computed at higher electronic energy than 8, this
energy difference is reversed when Gibbs free energies are considered.
S. Hoops, S. Sahle, R. Gauges, C. Lee, J. Pahle, N. Simus, M. Singhal,
L. Xu, P. Mendes, U. Kummer, Bioinformatics 2006, 22, 3067-3074.
See S.I. for details.
[
[
21]
22]
[
[
9]
18, 5701-5714.
10]
a) H. Grützmacher, Angew. Chem. Int. Ed. 2008, 47, 1814-1818; b) W.
Kuriyama, T. Matsumoto, O. Ogata, Y. Ino, K. Aoki, S. Tanaka, K. Ishida,
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