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Green Chemistry
Page 8 of 10
DOI: 10.1039/C7GC02764H
ARTICLE
Journal Name
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a) S. Werkmeister, J. Neumann, K. Junge, M. Beller, Chem.
Eur. J., 2015, 21 12226-12250. b) C. Gunanathan, D.
Milstein, Chem. Rev., 2014, 114, 12024-12087.
a) J. Zhang, G. Leitus, Y. Ben-David, D. Milstein, Angew.
Chem. Int. Ed., 2006, 45, 1113-1115. b) E. Fogler,
E.Balaraman, Y. Ben-David, G. Leitus, L. J.W. Shimon, D.
Milstein, Organometallics 2011, 30, 3826-3833. c) J. Zhang,
E. Balaraman, G. Leitus,D. Milstein, Organometallics 2011,
30, 5716-5724. d) Y. Sun, C. Koehler, R. Tan, V. T. Annibale,
were sampled every three seconds until the standard deviation
was below 0.1 mN.m–1. Three measurements were taken for
each sample. Thermogravimetric analysis (TGA) of the oils was
performed using a TGA Q5000 apparatus (TA Instruments) unit
under a nitrogen atmosphere to determine the degradation
temperatures. Samples between 2 and 10 mg were placed in
aluminum pans and heated from 25 to 400 °C at a heating rate
of 10 °C min-1. The degradation temperature Tdeg was
determined as the starting point of the degradation (range
with the highest slope of TGA curves). Thermal transitions
were determined by differential scanning calorimetry (DSC)
with a DSC Q100 calorimeter (TA Instruments) unit under a
nitrogen atmosphere, calibrated with a standard sample of
indium. Samples between 5 and 10 mg were sealed in
aluminum pans and measured over a temperature range of -80
°C until ca. 300 °C under the beginning of degradation with a
,
D. Song, Chem. Commun. 2011, 47, 8349-8351. e) D.
Spasyuk, D. G. Gusev, Organometallics 2012, 31, 5239−5242.
f) D. Spasyuk, S. Smith, D. G. Gusev Angew. Chem. Int. Ed.,
2012, 51, 2772 –2775. g) D. Spasyuk, S. Smith, D. G. Gusev
Angew. Chem. Int. Ed., 2013, 52, 2538 –2542. h) A. Acosta-
Ramirez, M. Bertoli, i) D. Spasyuk, C. Vicent, D. G. Gusev, J.
Am. Chem. Soc., 2015, 137, 3743–3746. j) G. A. Filonenko, M.
J. B. Aguila, E. N. Schulpen, R. van Putten, J. Wiecko, C.
Müller, L. Lefort, E. J. M. Hensen, E. A. Pidko, J. Am. Chem.
Soc., 2015, 137, 7620–7623. k) X. Tan, Y. Wang, Y. Liu, F.
Wang, L. Shi, K-H. Lee, Z. Lin, H. Lv, X. Zhang, Org. Lett., 2015,
17, 454-457. l) Tan, Q. Wang, Y. Liu, F. Wang, H. Lv, X. Zhang,
Chem. Commun., 2015, 51, 12193-12196. m) O. Ogata, Y.
Nakayama, H. Nara, M. Fujiwhara, Y. Kayaki. Org. Lett., 2016,
18, 3894–3897. n) D. Kim, L. Le, M. J. Drance, K. H. Jensen, K.
Bogdanovski, T. N. Cervarich, M. G. Barnard, N. J. Pudalov, S.
rate of 10 °C⋅
min-1; the samples were cooled with an
intercooler. The phase transitions of the products were
investigated, providing the melting temperature (Tm, as onset
of an endothermic peak on heating). Viscosities and densities
were measured simultaneously using a DMA4100/Lovis2000
densimeter/viscometer from Anton Paar, by rolling a ball
through a liquid-filled glass capillary (Ø 1.59 mm) inclined at a
defined angle. The liquid's viscosity is directly proportional to
the rolling time.
M. M. Knapp, A. R. Chianese, Organometallics, 2016, 35
982-989. o) Wang, X. Chen, B. Liu, Q-B. Liu, G. A. Solan, X.
Yang, W-H. Sun, Catal. Sci. Technol., 2017, , 1297-1304.
,
7
10 D. G. Gusev, M. Schlaf, Green Chem., 2012, 14, 1178–1188.
11 a) K. Junge, B. Wendt, H. Jiao, M. Beller, ChemCatChem
2014, 6, 2810-2814. b) T. P. Brewster, N. M. Rezayee, Z.
Culakova, M. S. Sanford, K. I. Goldberg, ACS Catal. 2016, 6,
3113−3117.
Acknowledgements
12 a) T. Zell, Y. Ben-David, D.Milstein, Angew. Chem. Int. Ed.,
2014, 53, 4685-4689. b) S. Werkmeister, K. Junge, B. Wendt,
E. Alberico, H. Jiao, W. Baumann, H. Junge, F. Gallou, M.
Beller, Angew. Chem. Int. Ed., 2014, 53, 8722 –8726. c) S.
Chakraborty, H. Dai, P. Bhattacharya, N. T. Fairweather, M. S.
This work was performed in partnership with the SAS PIVERT,
within the frame of Institut pour la Transition Energétique
Investment for the Future (“Investissements d’Avenir”). This
work was supported, as part of the Investments for the Future,
Gibson, J. A. Krause, H. Guan, J. Am. Chem. Soc., 2014, 136
7869−7872.
,
by the French Government under the reference ANR-001-01. 13 a) G. Zhang, K. V. Vasudevan, B. L. Scott, S. K. Hanson, J. Am.
Chem. Soc., 2013, 135, 8668−8681. b) D. Srimani, A.
Chevreul Institute (FR 2638), Ministère de l’Enseignement
Supérieur et de la Recherche, Région Nord – Pas de Calais and
FEDER are acknowledged for supporting and funding partially
this work. We acknowledge Mike Ortega for his help with
Mukherjee, A. F. G. Goldberg, G. Leitus, Y. Diskin-Posner, L. J.
W. Shimon, Y. Ben David, D. Milstein, Angew. Chem. Int. Ed.,
2015, 54, 12357-12360. c) T. J. Korstanje, J. I. van der Vlugt,
C. J. Elsevier, B. de Bruin, Science, 2015, 350, 298-302.
physicochemical studies, Celine Delabre for GC-MS analysis 14 a) S. Elangovan, M. Garbe, H. Jiao, A. Spannenberg, K. Junge,
M. Beller, Angew. Chem. Int. Ed., 2016, 55, 15364-15368. b)
R. van Putten, E. A. Uslamin, M. Garbe, C. Liu, A. Gonzalez-
de-Castro, M. Lutz, K. Junge, E. J. M. Hensen, M. Beller, L.
Lefort, E. A. Pidko, Angew. Chem. Int. Ed., 2017, 56, 7531-
7534. c) N. A. Espinosa-Jalapa, A. Nerush, L. J. W. Shimon, G.
Leitus, L. Avram, Y. Ben-David, D. Milstein, Chem. Eur. J.,
2017, 23, 5934-5938.
and Xavier Trivelli (UGSF) for his assistance with NMR
measurements.
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M. R. Meneghetti, S. M. Plentz Meneghetti, Catal. Sci.
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8 | J. Name., 2012, 00, 1-3
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