4
3. Arterburn, J. B.; Bryant, B. K.; Chen, D. ChemComm 2003, 1,
1890–1891.
Found: C 49.65, H 5.22, N 16.17. 1H NMR (DMSO-d6): δ 7.53
3
(s, H, CH), 5.41 (sex, JH-H = 6Hz, H, CH), 4.61-4.07 (m, 4H,
CH2), 3.42-1.95 (s, 12H, CH3); 13C{1H} (DMSO-d6): δ 170.04 (s,
C=O), 169.46 (s, C=O), 154.41 (s, C=O), 150.88 (s, C=O), 148.25
(s, C), 143.14 (s, CH), 106.13 (s, C), 69.42 (s, CH) 62.18 (s, CH2),
46.30 (s, CH2), 29.39 (s, CH3), 27.48 (s, CH3), 20.42 (s, 2CH3), IR
(KBr disc, cm-1): 1737-1655 (C=O) 3132, 1221(C-N). Yield 335
mg, 99%. L9: The product is a microcrystalline white solid with
mp = 210-211 ºC MS-EI. m/z = 280. Anal. Calcd. (%) for
C11H12N4O5: C 47.15, H 4.32, N 19.99. Found: C 47.12, H 4.34, N
4. Molander, G. a; Biolatto, B. J. Org. Chem. 2003, 68, 4302–4314.
5. Li, J.-H.; Zhu, Q.-M.; Xie, Y.-X. Tetrahedron 2006, 62, 10888–
10895.
6. Reyes, M. J.; Izquierdo, M. L.; Alvarez-Builla, J. Tetrahedron
Lett. 2004, 45, 8713–8715.
7. Chen, J.; Cammers-Goodwin, A. Tetrahedron Lett. 2003, 44,
1503–1506.
8. Hodgson, P. B.; Salingue, F. H. Tetrahedron Lett. 2004, 45, 685–
687.
1
19.93. H NMR (DMSO-d6): δ 8.04 (s, H, CH), 5.07 (s, 2H, CH2),
9. a) Tomori, H.; Fox, J. M.; Buchwald, S. L. J. Org. Chem. 2000,
65, 5334–5341. b) Corona-Rodríguez, M.; Hernández-Ortega, S.;
Valdés-Martínez, J.; Morales-Morales, D. Supramol. Chem. 2007,
19, 579–585. c) Baldovino-Pantaleón, O.; Hernández-Ortega, S.
Morales-Morales, D. Inorg. Chem. Commun. 2005, 8, 955–959. d)
Baldovino-Pantaleón, O.; Hernández-Ortega, S.; Morales-
Morales, D. Adv. Synth. Catal. 2006, 348, 236–242. e) Gutiérrez-
Márquez, R. A.; Crisóstomo-Lucas, C.; Reyes-Martinez, R.;
Hernández-Ortega, S.; Morales-Morales, D. Acta Cryst. Section E.
2014, E70, m200–m201. f) Gutiérrez-Márquez, R. A.;
Crisóstomo-Lucas, C.; Morales-Morales, D.; Hernández-Ortega,
S.; Acta Cryst. Section E. 2014, E70, m218. g) Cerón-Camacho,
R.; Morales-Morales, D.; Hernández, S.; Le Lagadec, R.; Ryabov,
A. D. Inorg. Chem. 2008, 47, 4988-4995. h) Olvera-Mancilla, J.;
López-Morales, S.; Palacios-Alquisira, J.; Morales-Morales, D.;
Le Lagadec, R.; Alexandrova, L. Polymer 2014, 55, 1656-1665.
10. Choi, B.; Kim, J.; Lee, E.-S.; Bang, D.; Sohn, S. Eur. J.
Pharmacol. 2011, 657, 167–172.
3.43-1.92 (s, 9H, CH3); 13C{1H} (DMSO-d6): δ 170.14 (s, C=O),
169.49 (s, C=O), 154.87 (s, C=O), 151.44 (s, C=O), 148.35 (s, C),
143.62 (s, CH), 108.81 (s, C), 47.63 (s, CH2), 29.91 (s, CH3),
27.89 (s, CH3), 21.51 (s, 2CH3), IR (KBr disc, cm-1): 1730-1654
(C=O) 3132, 1191(C-N). Yield 278 mg, 99%.
22. Supplementary data for ligand L8 have been deposited at the
Cambridge Crystallographic Data Centre. Copies of this
information are available free of charge on request from The
Director, CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK (Fax:
+44-1223-336033; e-mail deposit@ccdc.cam.ac.uk or www:
CCDC 1017248 (L8).
23. POV-Ray–The Persistence of Vision Raytracer, available at
24. ORTEP plots were created using Ortep-3 for Windows: Farugia,
L. J. Appl. Crystallogr. 1997, 30, 565.
25. Suzuki–Miyaura couplings were performed in glass tubes suitable
for microwave. Halopyridines (0.44 mmol), phenyl boronic acid
(65.17 mg, 0.53 mmol), Li2CO3 (63.7 mg, 0.89 mmol), 1 mol % of
11. Albaneze-Walker, J.; Murry, J. a.; Soheili, A.; Ceglia, S.;
Springfield, S. a.; Bazaral, C.; Dormer, P. G.; Hughes, D. L.
Tetrahedron 2005, 61, 6330–6336.
Pd(OAc)2 (1 mg, 4.45X10-3 mol) and
2 mol % of the
corresponding ligand in 3 mL of distilled water. The mixtures
were stirred and heated at 120 ºC under microwave radiation
during 10 min with a ramp of 1 min in a CEM Discover reactor
coupled to a CEM Explorer robotic system. The resulting reaction
mixture was cooled to room temperature and the mixture extracted
with CH2Cl2 (3 X 2 mL), the organic phase was treated with
anhydrous Na2SO4 after filter over celite and analyzed by Gas
Chromatography (GC–MS) on an Agilent 6890N GC with a 30.0
m DB-1MS capillary column coupled to an Agilent 5973 Inert
Mass Selective detector. Additional experiments of catalysis were
carried out under the same reactions conditions using different
bases Na2CO3, K2CO3, Li2CO3, Cs2CO3, Rb2CO3, NaOH, KOH,
Et3N and DIPEA.
12. Agrofoglio, L. a; Gillaizeau, I.; Saito, Y. Chem. Rev. 2003, 103,
1875–1916.
13. Khammultri, N.; Senamart, N.; Deepuppha, N.; Wongkhan, K.;
Jitchati, R. Adv. Mater. Res. 2012, 622-623, 236–240.
14. a) Phosphorus(III)Ligands in Homogeneous Catalysis: Design
and Synthesis; Kamer, P. C. J. van Leeuwen, P. W. N. M. Eds.;
Wiley-VCH Verlag GmbH: Weinheim, Germany, 2012. And
references therein. b) The Chemistry of Pincer Compounds;
Morales-Morales, D.; Jensen, C. M.; Elsevier; Amsterdam, 2007.
c) Morales-Morales, D.; Mini-Rev. Org. Chem., 2008, 5, 141-152.
d) Serrano-Becerra, J. M.; Morales-Morales, D. Curr. Org. Synth.
2009, 6, 169-192.
15. See for instance: a) Fortman, G. C.; Nolan, S. P. Chem. Soc. Rev.,
2011, 40, 5151–5169. And references therein. b) Zhang, C.;
Huang, J.; Trudell, M. L.; Nolan, S. P. J. Org. Chem. 1999, 64,
3804–3805.
26. Crabtree, R. H. Chem. Rev. 2012, 112, 1536–1554.
27. Landaeta, V. R.; Rodríguez-Lugo, R. E.; Rodríguez-Arias, E. N.;
Coll-Gómez, D. S.; González, T. Transition Met Chem. 2010, 35,
165–175.
16. Conelly-Espinosa, P.; Morales-Morales, D. Inorg. Chim. Acta
2010, 363, 1311–1315.
17. Crisóstomo-Lucas, C.; Toscano, R. A.; Morales-Morales, D.
Tetrahedron Lett. 2013, 54, 3116–3119.
18. a) Brackemeyer, D.; Hervé, A.; Schulte to Brinke, , Ch.; Jahnke,
−7844
M. C.; Hahn, F. E. J. Am. Chem. Soc. 2014, 136, 7841 . b)
Luo, F-T.; Lo, H-K. J. Organomet. Chem. 2011, 696, 1262-1265.
c) Schaper, L. A.; Hock, S. J.; Herrmann, W. A.; Khn, F. E.
Angew. Chem. Int. Ed. 2013, 52, 270–289. and references therein.
19. a) Kühl, O. Chem. Soc. Rev., 2007, 36, 592–607. And references
therein. b) Hahn, F. E. Angew. Chem. Int. Ed. 2006, 45, 1348–
1352. And references therein. c) Jahnke, M. C.; Hahn, F. E.
Angew. Chem. Int. Ed. 2008, 47, 3122–3172. And references
therein.
20. a) Pneumatikakis, G.; Yannopoulos, A.; Markopoulos, J.;
Angelopoulos, C. Inorganica Chim. Acta 1988, 152, 101–106. b)
Aoki, K.; Hoshino, M.; Okada, T.; Yamazaki, H.; Sekitawa, H. J.
Chem. Soc., Chem Commun. 1986, 314–316.
21. Ligands L7, L8 and L9 were all prepared the same way as
follows: in a round bottom flask 1 mmol of L4, L5 and L6 was set
to reflux in acetic anhydride (15mL) for 8 hours. After the
prescribed reaction, the resulting yellow reaction mixture is cooled
to room temperature and the solvent evaporated under vacuum to
produce white to light yellow microcrystalline powders that can be
recrystallized (CH2Cl2/hexane) for better quality products. L7:
The product is a microcrystalline white solid with mp = 98-99 ºC
MS-EI. m/z = 266. Anal. Calcd. (%) for C11H14N4O4: C 50.46, H
5.39, N 21.00. Found: C 50.43, H 5.45, N 21.04. 1H NMR
3
(DMSO-d6): δ 8.01 (s, H, CH), 4.49-4.37 (t, JH-H = 6Hz, 4H,
CH2), 3.42-1.96 (s, 9H, CH3); 13C{1H} (DMSO-d6): δ 169.99 (s,
C=O), 154.41 (s, C=O), 150.92 (s, C=O), 148.38 (s, C), 142.92 (s,
CH), 105.92 (s, C), 62.29 (s, CH2), 45.38 (s, CH2), 29.39 (s, CH3),
27.48 (s, CH3), 20.42 (s, CH3), IR (KBr disc, cm-1): 1739-1658
(C=O) 3113, 1247(C-N). Yield 260 mg, 98%. L8: The product is
a microcrystalline white solid with mp = 139-140 ºC MS-EI. m/z =
338. Anal. Calcd. (%) for C14H18N4O6: C 49.70, H 5.36, N 16.56.