7
11. Seayad, J.; List B. In Multicomponent Reactions; Zhu J. and
4.9. Synthesis of tertiary amines 5g and 6g
ACCEPTED MANUSCRIPT
Bienaymé H., Eds.; Wiley-VCH, Weinheim, 2005, pp 277-299.
12. Zhou, J. Chem. Asian J. 2010, 5, 422–434.
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1634.
Rh(acac)(CO)2
(2.1
mg,
8.1×10-3
mmol)
and
triphenylphosphine (4.2 mg, 0.016 mmol) were placed in the
autoclave. Then, a solution of 3-vinyl-indole 1g (116 mg, 0.81
mmol) and amine (1.6 mmol) in THF (4 mL) was added via
cannula, the autoclave was pressurized with 30 bar of CO/H2
(1:1) and the reaction was conducted for 18 h, upon stirring, at
65°C. After this period, the gas was switched from a mixture of
CO/H2 to H2 (30 bar) and the reaction was maintained for 10 h at
65 ºC.
15. Ambrosini, L. M.; Lambert, T. H. ChemCatChem 2010, 2, 1373–
1380.
16. Petricci, E.; Cini, E. Top Curr Chem. 2013, 342, 117–149.
17. Eilbracht, P.; Schmidt, A. Top. Organomet. Chem. 2006, 18, 65–
95.
18. Felpin, F. X.; Fouquet, E. ChemSusChem 2008, 1, 718–724.
19. Eilbracht, P.; Barfacker, L.; Buss, C.; Hollmann, C.; Kitsos-
Rzychon, B. E.; Kranemann, C. L.; Rische, T.; Roggenbuck, R.;
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4.9.1. 3-[1-(Piperidin-1-yl)propan-2-yl]-1H-indole (5g)
1
Yield: 0.175 g (89%), beige solid. H NMR (400.1 MHz,
20. Raoufmoghaddam, S.; Drent, E.; Bouwman, E. Adv. Synth. Catal.
2013, 355, 717–733.
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24. Subhani, M. A.; Müller, K.-S.; Koç, F.; Eilbracht, P. Org. Biomol.
Chem. 2009, 7, 4000–4008.
CDCl3): δ 1.41 (d, J= 6.8 Hz, 3H, CH3), 1.41 – 1.47 (m, 2H,
CH2), 1.55 – 1.71 (m, 4H, CH2), 2.43 – 2.63 (m, 6H, N-CH2),
3.31 – 3.43 (m, 1H, CHCH3), 7.04 – 7.65 (m, 5H, ArH), 8.21 (br
s, 1H, NH) ppm. 13C NMR (100 MHz, CDCl3): δ 18.7, 23.4,
24.9, 27.5, 54.0, 65.2, 110.3, 117.9, 118.2, 119.4, 120.0, 120.7,
125.7, 135.4 ppm. HRMS (ESI+) calcd for C16H23N2 [M+H]+:
243.1856. Found: 243.1857.
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4.9.2. 3-(1-Morpholinopropan-2-yl)-1H-indole (6g)
1
Yield: 0.162 g (82%), beige solid. H NMR (400.1 MHz,
CDCl3): δ 1.41 (d, J=6.8 Hz, 3H, CH3), 2.35 – 2.76 (m, 6H, N-
CH2) 3.20 – 3.41 (m, 1H, CHCH3), 3.57 – 3.81 (m, 4H, O-CH2),
7.00 – 7.66 (m, 5H, ArH), 8.01 (br s, 1H, NH) ppm. 13C NMR
(100.6 MHz, CDCl3): δ 19.6, 28.4, 54.2, 66.0, 67.2, 111.4, 119.2,
119.3, 120.4, 120.9, 122.1, 126.9, 136.6 ppm. HRMS (ESI+)
calcd for C15H21N2O [M+H]+: 245.1648. Found: 243.1646.
29. Dutta, B.; Schwarz, R.; Omar, S.; Natour, S.; Abu-Reziq, R. Eur.
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Acknowledgments
32. Liu, G.; Huang, K.; Cai, C.; Cao, B.; Chang, M.; Wu, W.; Zhang,
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33. Hamers, B.; Koscius-Morizet, E.; Muller, C.; Vogt, D.
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The authors are thankful to FCT - Fundação para a Ciência e a
Tecnologia (Portuguese Foundation for Science and Technology)
and FEDER (European Regional Development Fund) through the
34. Wu, L.; Fleischer, I.; Jackstell, R.; Profir, I.; Franke, R.; Beller, M.
J. Am. Chem. Soc. 2013, 135, 14306−14312.
35. Gülak, S.; Wu, L.; Liu, Q.; Franke, R.; Jackstell, R.; Beller, M.
Angew. Chem. Int. Ed. 2014, 53, 7320 –7323.
36. Dong, K.; Fang, X.; Jackstell, R.; Beller, M.Chem. Commun.
2015, 51, 5059–5062.
COMPETE
Programme
(Operational
Programme
for
Competitiveness) for the financial support to Coimbra Chemistry
Centre (PEst-OE/QUI/UI0313/2014, UID/QUI/00313/2013).
NMR data was collected at the UC-NMR facility which is
supported in part by FEDER through the COMPETE Programme
37. Peixoto, A. F.; Pereira, M. M.; Silva, A. M. S.; Foca, C. M.;
Bayón, J. C.; Moreno, M. J. S. M; Beja,A. M.; Paixão, J. A.;
Silva, M. R. J. Mol. Catal. Chem. A 2007, 275, 121–129.
38. Costa, G. N.; Carrilho, R. M. B.; Dias, L. D.; Viana, J. C.; Aquino,
G. L. B.; Pineiro, M.; Pereira, M. M. J. Mol. Catal. A: Chem.
2016, 416, 73–80.
and
by
National
Funds
through
FCT
grants
REEQ/481/QUI/2006, RECI/QEQ-QFI/0168/2012, CENTRO-
07-CT62-FEDER-002012, and Rede Nacional de Ressonância
Magnética Nuclear (RNRMN).RMBC also thanks FCT for a
post-doc grant (SFRH/BPD/100537/2014).
39. Filipe, H. A. L.; Coreta-Gomes, F. M.; Velazquez-Campoy, A.;
Almeida, A. R.; Peixoto, A. F.; Pereira, M. M.; Vaz, W. L. C.;
Moreno, M. J. J. Phys. Chem. B 2013, 117, 3439–3448.
40. van der Veen, L. A.; Keeven, P. H.; Schoemaker, G. C.; Reek, J.
N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Lutz, M.;
Spek, A. L. Organometallics 2000, 19, 872–883.
41. van Leeuwen, P. W. N. M.; Roobeek, C. F. J. Organomet. Chem.
1983, 258, 343–350.
42. Carrilho, R. M. B.; Abreu, A. R.; Petocz, G.; Bayón, J. C.;
Moreno, M. J. S. M.; Kollár, L.; Pereira, M. M. Chem. Lett. 2009,
38, 844–845.;
43. Carrilho, R. M. B.; Neves, A. C. B.; Lourenço, M. A.; Abreu, A.
R.; Rosado, M. T.; Abreu, P. E.; Eusébio, M. E. S.; Kollár, L.;
Bayón, J. C.; Pereira, M. M.; J. Organomet. Chem. 2012, 698, 28–
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