ACCEPTED MANUSCRIPT
5
conditions: Agilent J&W CG Column HP-5 30 m×25 mm×0,25
m, helium as carrier gas, 230 ºC injector T, 250 ºC detector T,
(13) Brown, J. W.; Jarenwattananon, N. N.; Otto, T.; Wang, J. L.;
Glöggler, S.; Bouchard, L.-S. Catal. Commun. 2015, 65, 105–107.
ꢀ
–
1
(14) Lara-Ochoa, F.; Sandoval-Minero, L. C.; Espinosa-Pérez, G.
2
0 psi head column pressure, 2 mL min flux, oven temperature
Tetrahedron Lett. 2015, 56, 5977–5979.
–1
program 70 ºC (1 min), 20 ºC min , 250 ºC (7.5 min), retention
time 11.3 min.; δ (400 Mhz, CDCl ) 7.35 (d, 2H, J= 8.7 Hz),
.95 (d, 1H, J= 16.2 Hz), 6.83–6.80 (m, 3H), 6.57 (d, 2H, J= 1.9
Hz), 6.29 (t, 1H, J= 1.8 Hz), 3.73 (s, 9H); δ (100.6 Mhz, CDCl
APT) 161,0 (C), 159,4 (C), 139,7 (C), 130,0 (C), 128,8 (CH),
27,8 (CH), 126,6 (CH), 114,2 (CH), 99,7 (CH), 55,3 (CH ); m/z
(
15) Perez, C. C.; Pena, J. M.; Correia, C. R. D. New J. Chem. 2014, 38,
H
3
3933–3938.
6
(16) Schmidt, B.; Elizarov, N.; Berger, R.; Hölter, F. Org. Biomol. Chem.
013, 11, 3674–3691.
2
C
3
,
(
(
(
17) Nobre, S. M.; Muniz, M. N.; Seferin, M.; da Silva, W. M.; Monteiro,
A. L. Appl. Organomet. Chem. 2011, 25, 289–293.
1
3
18) Moro, A. V.; Cardoso, F. S. P.; Correia, C. R. D. Tetrahedron Lett.
2008, 49, 5668–5671.
19) Yamada, Y. M. A.; Takeda, K.; Takahashi, H.; Ikegami, S.
+
(
EI) 270 (M ).
4.3. (E)-5-(4-hydroxystyryl)benzene-1,3-diol (resveratrol, 1)
Tetrahedron 2004, 60, 4097–4105.
(
(
20) Botella, L.; Nájera, C. Tetrahedron 2004, 60, 5563–5570.
21) Jeffery, T.; Ferber, B. Tetrahedron Lett. 2003, 44, 193–197.
To a solution of 4 (270 mg 1 mmol) in 20 mL of anhydrous
dichloromethane at –78 ºC, 4.5 mL of a solution 1M of boron
(22) Andrus, M. B.; Liu, J.; Meredith, E. L.; Nartey, E. Tetrahedron Lett.
003, 44, 4819–4822.
3
7
2
tribromide in dichloromethane was added dropwise. The
resulting solution was magnetically stirred at –78 ºC for 2 h.
After this time, the solution was let to reach room temperature,
and then it was poured onto brine. The organic phase was
separated and the aqueous phase was extracted with acetonitrile
(
(
23) Guiso, M.; Marra, C.; Farina, A. Tetrahedron Lett. 2002, 43, 597–598.
24) Martínez, A. V.; Mayoral, J. A.; García, J. I. Appl. Catal. Gen. 2014,
4
72, 21–28.
(25) Martínez, A. V.; Invernizzi, F.; Leal-Duaso, A.; Mayoral, J. A.; García,
J. I. RSC Adv. 2015, 5, 10102–10109.
(
4×30 mL). The combined organic phases were dried with
(26) Martínez, A. V.; Leal-Duaso, A.; García, J. I.; Mayoral, J. A. RSC Adv.
015, 5, 59983–59990.
2
anhydrous MgSO , filtered and the solvent was removed at
4
(
(
(
27) Teranishi, T.; Miyake, M. Chem. Mater. 1998, 10, 594–600.
28) Li, Y.; Boone, E.; El-Sayed, M. A. Langmuir 2002, 18, 4921–4925.
29) As a referee pointed out, the resveratrol precursor appears depicted
twice on the chromatogram in Fig. 2, which may result confusing at the
first sight. In fact, the red line in the figure represents the UV
absorbance of the sample, and the blue line the composition of the
eluent. The resveratrol precursor starts leaving the column in the
minute 12, at a low concentration. In the minute 14, the eluent is
changed to pure ethyl acetate, which provokes that most of the
resveratrol precursor was collected in the fractions between the minute
15 and the 16. There are no two separated peaks, but one irregularly
shaped peak representing different concentrations of the target
compound in the collected fractions due to the different polarity of the
eluent.
reduced pressure. The resulting product was purified by medium
pressure column chromatography (Combiflash®) using a silica
gel column and a mixture hexane /ethyl acetate 1:1 as eluent,
leading to a colourless solid (210 mg, 92%) characterized by
3
8,39
NMR;
[Found C 73.35 H 5.36 requires C, 73.67, H, 5.30];
GC conditions: Agilent J&W CG Column HP-5 30 m×25
mm×0,25 ꢀm, helium as carrier gas, 230 ºC injector T, 250 ºC
–
1
detector T, 20 psi head column pressure, 2 mL min flux, oven
–
1
temperature program 70 ºC (1 min), 20 ºC min , 250 ºC (7.5
min), retention time 12.9 min.; δH (400 Mhz, acetone-d ) 7.30–
6
7
6
.27 (m, 2H), 6.88 (d, 1H, J= 16.3 Hz), 6.75 (d, 1H, J= 16.3 Hz),
.71–6.69 (m, 2H), 6.41 (d, 2H, J= 2.2 Hz), 6.14 (d, 1H, J= 2.2
(30) Gruber, A. S.; Pozebon, D.; Monteiro, A. L.; Dupont, J. Tetrahedron
Hz), 3.64 (s, 1H), 2.88 (s, 2H); δ
59.0 (C), 158.2 (C), 140.9 (C), 130.0 (C), 129.1 (CH), 128.7
CH), 126.6 (CH), 116.4 (CH), 105.7 (CH), 102.7 (CH); m/z (EI)
C 6
(100.6 Mhz, acetone-d , APT)
Lett. 2001, 42, 7345–7348.
1
(31) Alimardanov, A.; Schmieder-van de Vondervoort, L.; de Vries, A. H.
M.; de Vries, J. G. Adv. Synth. Catal. 2004, 346, 1812–1817.
(32) Cassol, C. C.; Umpierre, A. P.; Machado, G.; Wolke, S. I.; Dupont, J.
J. Am. Chem. Soc. 2005, 127, 3298–3299.
(
2
+
28 (M ).
(
33) Astruc, D. Inorg. Chem. 2007, 46, 1884–1894.
Acknowledgments
(34) Dupont, J.; Scholten, J. D. Chem. Soc. Rev. 2010, 39, 1780–1804.
(
(
35) Scholten, J. D.; Leal, B. C.; Dupont, J. ACS Catal. 2012, 2, 184–200.
36) Lebel, H.; Ladjel, C.; Bréthous, L. J. Am. Chem. Soc. 2007, 129,
Financial support from the Spanish MINECO (project
CTQ2014-52367-R), the European Social Fund (ESF) and the
Gobierno de Aragón (Grupo Consolidado E11) is gratefully
acknowledged.
1
3321–13326.
(37) Pettit, G. R.; Grealish, M. P.; Jung, M. K.; Hamel, E.; Pettit, R. K.;
Chapuis, J.-C.; Schmidt, J. M. J. Med. Chem. 2002, 45, 2534–2542.
(38) Lee, D.; Bhat, K. P. L.; Fong, H. H. S.; Farnsworth, N. R.; Pezzuto, J.
M.; Kinghorn, A. D. J. Nat. Prod. 2001, 64, 1286–1293.
(
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