Please do not adjust margins
Page 9 of 10
Green Chemistry
Journal Name
ARTICLE
1
1
mmol) and p-xylene (4 mmol, GC internal standard) in a
specified solvent was transferred into the autoclave under
Arellano-Garcia, A. Seidel-Morgenstern, and C. Hamel, Chem.
DOI: 10.1039/C8GC03750G
Eng. Sci., 2014, 115, 31.
4 E. Schafer, Y. Brunsch, G. Sadowski and A. Behr, Ind. Eng.
Chem. Res., 2012, 51, 10296.
argon; then the autoclave was pressurized to 40 atm (CO/H
2
=
1
/1) and heated to the indicated temperature. Finally, the
reaction solution was stirred with a magnetic stirrer for the 15 A. Behr, D. Obst and B. Turkowski, J. Mol. Catal. A-Chem.,
2
005, 226, 215.
reported time.
1
6 (a) P. Pongracz, B. Bartal, L. Kollar and L. T. Mika, J.
Organomet. Chem., 2017, 847, 140; (b) P. Pongrácz, L. Kollár,
and L. T. Mika, Green Chem., 2016, 18, 842.
Reaction products were analyzed/identified by gas
chromatography/mass spectrometry (GC-MS) on a Shimadzu
QP2010-PLUS equipment operating at 70 eV. Product 6b was
separated (as a mixture of four stereoisomers) by column
chromatography (silica gel 60, hexane/ethyl acetate mixtures)
and identified by NMR spectroscopy (DEPT, COSY, HMQC and
HMBC experiments) on a Bruker 400 MHz spectrometer
1
1
7 F. G. Delolo, K. C. B. Oliveira, E. N. dos Santos, and E. V.
Gusevskaya, Molec. Cat., 2019, 462, 1.
8 A. C. Faria, K. C. B. Oliveira, A. C. Monteiro, E. N. dos Santos
and E. V. Gusevskaya, Catal. Today, 2018, DOI:
doi.org/10.1016/j.cattod.2018.10.024
1
9 P. Neubert, S. Fuchs and A. Behr, Green Chem., 2015, 17,
3
(CDCl , TMS). Spectroscopic data for product 6b are presented
4
045.
in ESl
20 D. Prat, A. Wells, J. Hayler, H. Sneddon, C. R. McElroy, S.
Abou-Shehada and P. J. Dunn, Green Chem., 2016, 18, 288.
2
1 C. M. Alder, J. D. Hayler, R. K. Henderson, A. M. Redman, L.
Shukla, L. E. Shuster and H. F. Sneddon, Green Chem., 2016,
Conflicts of interest
There are no conflicts to declare.
1
8, 3879.
22 (a) C. M. Bernt, G. Bottari, J. A. Barrett, S. L. Scott, K. Barta
and P. C. Ford, Catal. Sci. Technol., 2016, 6, 2984. (b) S. Gillet,
M. Aguedo, L. Petitjean, A. R. C. Morais, A. M. da Costa
Lopes, R. M. Łukasik and P. T. Anastas, Green Chem.,
Acknowledgements
2
017, 19, 4200. (c) K. Leiva, R. Garcia, C. Sepulveda, D.
Laurenti, C. Geantet, M. Vrinat, J. L. Garcia-Fierro and N.
Escalona, Cat. Today, 2017, 296, 228.
CNPq, CAPES, FAPEMIG, and INCT-Catálise (Brazil) are
gratefully thanked for the financial support and fellowships.
2
2
2
3 A. V. Granato, A. G. Santos and E. N. dos Santos,
ChemSusChem, 2017, 10, 1832.
4 R. M. Deshpande and R. V. Chaudhari, Ind. Eng. Chem. Res.,
Notes and references
1
988, 27, 1996.
5 E. Fernandez, A. Polo, A. Ruiz, C. Claver and S. Castillon,
Chem. Commun. (Cambridge), 1998, DOI: 10.1039/a804220i,
1
(a) P. W. N. M. van Leeuwen and C. Claver (Eds.), Rhodium
Catalyzed Hydroformylation, Kluwer Academic Publishers,
Dordrecht, 2000; (b) A. Börner and R. Franke,
1
803.
2
2
2
2
3
6 M. C. de Freitas, C. G. Vieira, E. N. dos Santos and E. V.
Gusevskaya, ChemCatChem., 2013, 5, 1884.
Hydroformylation:
Fundamentals,
Processes,
and
Applications in Organic Synthesis, Wiley-VCH, Weinheim,
Germany, 2016.
7 J. Norinder, C. Rodrigues and A. Börner, J. Mol. Cat A-Chem.,
2
014, 391, 139.
2
(a) R. Franke, D. Selent and A. Börner, Chem. Rev., 2012, 112,
8 P. J. Dyson and P. G. Jessop, Catal. Sci. Technol., 2016, 6,
302.
5
675. (b) H.-W. Bohnen, B. Cornils, Adv. Catal., 2002, 47, 1.
3
(
c) J. Hibbel, E. Wiebus, B. Cornils, Chem. Ing. Tech. 2013, 85,
9 I. Wender, S. Metlin, S. Ergun, H. W. Sternberg and H.
Greenfield, J. Am. Chem. Soc., 1956, 78, 5401.
1
853. (d) C. W. Kohlpaintner, R. W. Fischer, B. Cornils, Appl.
Catal. A, 2001, 221, 219.
0 WO9505354-A1; AU9476141-A; US5488174-A; EP714385-A1;
BR9407280-A; JP9501917-W; CN1129438-A; EP714385-B1;
DE69414578-E; ES2123823-T3; SG55063-A1; KR338320-B;
CN1072633-C; CA2169651-C; JP3744536-B2.
1 US4533756-A.
2 H. Klein, R. Jackstell and M. Beller, Chem. Commun., 2005,
DOI: 10.1039/b418350a, 2283.
3
4
E. V. Gusevskaya, J. Jimenez-Pinto and A. Börner,
ChemCatChem, 2014, 6, 382.
C. J. Clarke, W. C. Tu, O. Levers, A. Bröhl and J. P. Hallett,
Chem. Rev., 2018, 118, 747.
3
3
5
6
Y. L. Gu and F. Jerome, Chem. Soc. Rev., 2013, 42, 9550.
W. Alsalahi and A. M. Trzeciak, J. Mol. Catal. A-Chem., 2015,
4
08, 147.
3
3 M. Ahmed, R. P. J. Bronger, R. Jackstell, P. C. J. Kamer, P. W.
N. M. van Leeuwen and M. Beller, Chem. Eur. J., 2006, 12,
7
8
9
R. M. Deshpande, S. S. Divekar, B. M. Bhanage and R. V.
Chaudhari, J. Mol. Catal., 1992, 77, L13.
8
979.
R. Tudor and A. Shah, Johns. Matthey Technol. Rev., 2017,
3
3
4 S. Sirol and P. Kalck, New J. Chem., 1997, 21, 1129.
5 J. G. da Silva, H. J. V. Barros, E. N. dos Santos and E. V.
Gusevskaya, Appl. Catal., A., 2006, 309, 169.
6
1, 246.
(a) I. T. Horvath and J. Rabai, Science, 1994, 266, 72; (b) D. F.
Foster, D. J. Adams, D. Gudmunsen, A. M. Stuart, E. G. Hope,
and D. J. Hamilton, Chem. Commun., 2002, 0, 722.
3
3
6 C. G. Vieira, E. N. dos Santos and E. V. Gusevskaya, Appl.
Catal., A., 2013, 466, 208.
1
0 (a) L. Tao, M. M. Zhong, J. Chen, S. Jayakumar, L. N. Liu, H. Li
and Q. H. Yang, Green Chem., 2018, 20, 188; (b) J. Dupont, R.
F. de Souza, and P. A. Z. Suarez, Chem. Rev., 2002, 102, 3667;
7 M. C. de Freitas, K. C. B. de Oliveira, A. de Camargo Faria, E.
N. dos Santos and E. V. Gusevskaya, Catal. Sci. Technol.,
2
014, 4, 1954.
(
c) M. Ali, A. Gual, G. Ebeling, and J. Dupont, ChemCatChem,
3
3
8 J. G. da Silva, H. J. V. Barros, A. Balanta, A. Bolanos, M. L.
Novoa, M. Reyes, R. Contreras, J. C. Bayon, E. V. Gusevskaya
and E. N. dos Santos, Appl. Catal., A., 2007, 326, 219.
9 O. Diebolt, H. Tricas, Z. Freixa and P. W. N. M. van Leeuwen,
ACS Catal., 2013, 3, 128.
2
014, 6, 2224.
1
1
1 D. Koch and W. Leitner, J. Am. Chem. Soc., 1998, 120, 13398.
2 A. Jorke, T. Gaide, A. Behr, A. Vorholt, A. Seidel-
Morgenstern, and C. Hamel, Chem. Eng. J., 2017, 313, 382.
This journal is © The Royal Society of Chemistry 20xx
J. Name., 2013, 00, 1-3 | 7
Please do not adjust margins