Advanced Synthesis & Catalysis
10.1002/adsc.201701607
2
006, 45, 1113-1115; c) W. Kuriyama, T.
Reaction monitoring
Matsumoto, O. Ogata, Y. Ino, K. Aoki, S.
Tanaka, K. Ishida, T. Kobayashi, N. Sayo, T.
Saito, Org. Process Res. Dev 2012, 16, 166-
A 100 ml hastelloy autoclave with mechanical stirrer
and a high pressure sample outlet was charged with
Me
[
Ru(NNS )(PPh
3
)Cl ] C1a (23 mg, 0.038 mmol,
2
171; d) T. vom Stein, M. Meuresch, D.
0
.25 mol%), ester substrate 1b (15 mmol), 30 ml of
toluene, KOtBu (41 mg, 0.38 mmol, 2.5 mol%), and
000 µl of anhydrous n-dodecane under an argon
atmosphere. The autoclave vessel was flushed with
0 bar of N three times, with 10 bar of H two times,
then pressurized to 30 bar H and heated to the
Limper, M. Schmitz, M. Holscher, J. Coetzee,
D. J. Cole-Hamilton, J. Klankermayer, W.
Leitner, J. Am. Chem. Soc. 2014, 136, 13217-
1
2
2
2
13225; e) H. T. Teunissen, C. J. Elsevier,
2
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desired temperature and stirred. During the reaction,
samples in the size of approximately 100 µl were
taken, filtered over celite and diluted with 1 ml of
acetone. Results for 40°C are shown in figure 3. For
exoperiments at 80°C and 100°C please refer to the
supporting information.
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Hydrogenations:
A 100 ml hastelloy autoclave with mechanical stirrer
was charged with the desired amount of
Me
Ru(NNS )(PPh
3
)Cl
2
, KOtBu (41 mg, 0.38 mmol, 2.5
mol%), ester substrate (15 mmol) and 30 ml of
toluene under an argon atmosphere. If lower amounts
of substrates were used solvent and catalyst/base
were adjusted accordingly. The autoclave vessel was
7, 3735-3740; b) T. J. Korstanje, J. I. van der
Vlugt, C. J. Elsevier, B. de Bruin, Science
2015, 350, 298-302; c) D. Srimani, A.
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D. Milstein, Angew. Chem. Int. Ed. Engl.
2015, 54, 12357-12360.
a) S. Elangovan, M. Garbe, H. Jiao, A.
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b) R. van Putten, E. A. Uslamin, M. Garbe, C.
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flushed with 20 bar of N
2
three times, with 10 bar of
to a desired pressure,
H
2
two times, then filled with H
2
heated to the desired temperature and stirred for the
indicated time. During the reaction time the vessel
was repressurized to keep the pressure over 20 bars.
The pressure vessel was cooled down to room
temperature and then carefully depressurized. Then
[
5]
0
.1 ml of the reaction mixture was filtered through
celite and rinsed with acetone (1 ml), and analyzed by
gas chromatography and/or the alcohol fraction
isolated.
Acknowledgements
2
017, 56, 7531-7534; c) M. B. Widegren, G.
We thank Dr. C. Fischer, A. Koch, S. Buchholz, S. Schareina, A.
Lehmann, and S. Rosmeisl at the LIKAT analytical department
for their indispensable support. We thank the State of
Mecklenburg-Vorpommern for financial support.
J. Harkness, A. M. Z. Slawin, D. B. Cordes,
M. L. Clarke, Angew. Chem. 2017, 129,
5919-5922; d) M. Garbe, K. Junge, M. Beller,
Eur. J. Org. Chem. 2017, 2017, 4344-4362;
e) N. A. Espinosa-Jalapa, A. Nerush, L. J. W.
Shimon, G. Leitus, L. Avram, Y. Ben-David,
D. Milstein, Chem. Eur. J. 2017, 23, 5934-
Conflict of interest
The authors declare no conflict of interest.
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