Mild regiospecific synthesis of 1-alkoxy-isochromenes catalyzed by well-defined [silver(I)(pyridine-containing ligand)] complexes

Journal of Organic Chemistry

Volumn 79, Issue 8, 2014, Pages 3494-3505

  Dellacqua, Monica ^a   Castano, Brunilde ^a   Cecchini, Clara ^a   Pedrazzini, Tommaso ^a   Pirovano, Valentina ^a   Rossi, Elisabetta ^a   Caselli, Alessandro ^a   Abbiati, Giorgio ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PYRIDINE;

MACROCYCLICS; MILD REACTION CONDITIONS; NMR EXPERIMENTS; REACTION MECHANISM; REACTION YIELDS; REGIOSPECIFIC SYNTHESIS; SILVER COMPLEXES; SILVERS (I);

LIGANDS;

SILVER DERIVATIVE;

ADDITION REACTION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; CYCLOISOMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; SONOGASHIRA REACTION; SYNTHESIS;

BENZALDEHYDES; BENZOPYRANS; CATALYSIS; COORDINATION COMPLEXES; LIGANDS; MACROCYCLIC COMPOUNDS; SILVER;

EID: 84899013234     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo5002559     Document Type: Article

References (62)

1. Attardo, G.; Wang, W.; Breining, T.; Li, T.; St-Denis, Y.; Kraus, J.-L. Int. Patent WO 9 512 588, 1995.
2. Wang, W.; Li, T.; Milbum, R.; Yates, J.; Hinnant, E.; Luzzio, M. J.; Noble, S. A.; Attardo, G. Bioorg. Med. Chem. Lett. 1998, 8, 1579-1584
3. Ankisetty, S.; Amsler, C. D.; Clintock, J. B.; Baker, B. J. J. Nat. Prod. 2004, 67, 1172-1174
4. Nakamura, I.; Yamamoto, Y. Chem. Rev. 2004, 104, 2127-2198
5. Zeni, G.; Larock, R. C. Chem. Rev. 2004, 104, 2285-2310
6. Alonso, F.; Beletskaya, I. P.; Yus, M. Chem. Rev. 2004, 104, 3079-3160
7. Godet, T.; Vaxelaire, C.; Michel, C.; Milet, A.; Belmont, P. Chem. - Eur. J. 2007, 13, 5632-5641
8. DellAcqua, M.; Facoetti, D.; Abbiati, G.; Rossi, E. Synthesis 2010, 2367-2378 and references cited therein
9. Godet, T.; Bosson, J.; Belmont, P. Synlett 2005, 2786-2790
10. Cikotiene, I.; Morkunas, M.; Motiejaitis, D.; Brukstus, A. Synlett 2008, 1693-1967
11. Kanazawa, C.; Ito, A.; Terada, M. Synlett 2009, 638-642
12. Asao, N.; Nogami, T.; Takahashi, K.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 764-765
13. Mondal, S.; Nogami, T.; Asao, N.; Yamamoto, Y. J. Org. Chem. 2003, 68, 9496-9498
14. Patil, N. T.; Yamamoto, Y. J. Org. Chem. 2004, 69, 5139-5142
15. Rudys, S.; Cikotiene, I.; Rios-Luci, C.; Perez-Roth, E.; Padron, J. M. Bioorg. Med. Chem. Lett. 2010, 20, 1504-1506
16. Cikotiene, I.; Buksnaitiene, R.; Rudys, S.; Morkunas, M.; Motiejaitis, D. Tetrahedron 2010, 66, 251-258
17. Enomoto, T.; Girard, A.-L.; Takemoto, Y.; Yasui, Y. J. Org. Chem. 2009, 74, 9158-9164
18. Obika, S.; Kono, H.; Yasui, Y.; Yanada, R.; Takemoto, Y. J. Org. Chem. 2007, 72, 4462-4468
19. Handa, S.; Slaughter, L. M. Angew. Chem., Int. Ed. 2012, 51, 2912-2915
20. Barluenga, J.; Vázquez-Villa, H.; Ballesteros, A.; González, J. M. J. Am. Chem. Soc. 2003, 125, 9028-9029
21. Barluenga, J.; Vásquez-Villa, H.; Merino, I.; Ballesteros, A.; González, J. M. Chem. - Eur. J. 2006, 12, 5790-5805
22. Yue, D.; Cà, N. D.; Larock, R. C. J. Org. Chem. 2006, 71, 3381-3388
23. Yue, D.; Cà, N. D.; Larock, R. C. Org. Lett. 2004, 6, 1581-1584
24. Enders, D.; Grondal, C.; Hüttl, M. R. M. Angew. Chem., Int. Ed. 2007, 46, 1570-1581
25. Tietze, L. F.; Brasche, G.; Gericke, K. Domino Reactions in Organic Synthesis; Wiley-VCH: Weinheim, Germany, 2006.
26. Guo, H.-C.; Ma, J.-A. Angew. Chem., Int. Ed. 2006, 45, 354-366
27. Tietze, L. F. Chem. Rev. 1996, 96, 115-136
28. Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. 1993, 32, 131-163
29. Padwa, A.; Bur, S. K. Tetrahedron 2007, 63, 5341-5378
30. Tietze, L. F.; Rackelmann, N. Pure Appl. Chem. 2004, 76, 1967-1983
31. Padwa, A. Pure Appl. Chem. 2003, 75, 47-62
32. Abbiati, G.; Arcadi, A.; Chiarini, M.; Marinelli, F.; Pietropaolo, E.; Rossi, E. Org. Biomol. Chem. 2012, 7801-7808
33. DellAcqua, M.; Abbiati, G.; Arcadi, A.; Rossi, E. Org. Biomol. Chem. 2011, 7836-7848
34. DellAcqua, M.; Facoetti, D.; Arcadi, A.; Abbiati, G.; Rossi, E. Synlett 2010, 2672-2676
35. Alfonsi, M.; DellAcqua, M.; Facoetti, D.; Arcadi, A.; Abbiati, G.; Rossi, E. Eur. J. Org. Chem. 2009, 2852-2862
36. Facoetti, D.; Abbiati, G.; dAvolio, L.; Ackermann, L.; Rossi, E. Synlett 2009, 2273-2276
37. Facoetti, D.; Abbiati, G.; Rossi, E. Eur. J. Org. Chem. 2009, 2872-2882
38. DellAcqua, M.; Facoetti, D.; Abbiati, G.; Rossi, E. Tetrahedron 2011, 67, 1552-1556
39. Stetter, H.; Frank, W.; Mertens, R. Tetrahedron 1981, 37, 767-772
40. Aime, S.; Botta, M.; Crich, S. G.; Giovenzana, G. B.; Jommi, G.; Pagliarin, R.; Sisti, M. Inorg. Chem. 1997, 36, 2992-3000
41. Aime, S.; Gianolio, E.; Corpillo, D.; Cavallotti, C.; Palmisano, G.; Sisti, M.; Giovenzana, G. B.; Pagliarin, R. Helv. Chim. Acta 2003, 86, 615-632
42. Caselli, A.; Cesana, F.; Gallo, E.; Casati, N.; Macchi, P.; Sisti, M.; Celentano, G.; Cenini, S. Dalton Trans. 2008, 4202-4205
43. Castano, B.; Guidone, S.; Gallo, E.; Ragaini, F.; Casati, N.; Macchi, P.; Sisti, M.; Caselli, A. Dalton Trans. 2013, 42, 2451-2562
44. Castano, B.; Zardi, P.; Honemann, Y. C.; Galarneau, A.; Gallo, E.; Psaro, R.; Caselli, A.; Dal Santo, V. RSC Adv. 2013, 3, 22199-22205
45. Castano, B.; Pedrazzini, T.; Sisti, M.; Gallo, E.; Ragaini, F.; Casati, N.; Caselli, A. Appl. Organomet. Chem. 2011, 25, 824-829
46. Reichardt, C. Solvents and Solvent Effects in Organic Chemistry, 3 rd ed.; Wiley-VCH: Weinheim, Germany, 2003.
47. Díaz-Torres, R.; Alvarez, S. Dalton Trans. 2011, 40, 10742-10750
48. Antoniotti, S.; Dalla, V.; Duñach, E. Angew. Chem., Int. Ed. 2010, 49, 7860-7888
49. Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 50, 4467-4469
50. Chinchilla, R.; Nájera, C. Chem. Rev. 2007, 107, 874-922
51. The spectrum was compared with the spectrum of pure 2-(2-(4- methoxyphenyl)-2-oxoethyl) benzaldehyde reported in the literature: Zhu, S.; Liang, R.; Jiang, H.; Wu, W. Angew. Chem., Int. Ed. 2012, 51, 10861-10865
52. Belmont, P. In Silver in Organic Chemistry; Harmata, M., Ed.; John Wiley and Sons, Inc.: Hoboken, NJ, 2010; pp 143-165.
53. For a recent review on - and π-electrophilic Lewis acids see: Yamamoto, Y. J. Org. Chem. 2007, 72, 7817-7831
54. - salts have been isolated and characterized, see: Tovar, J. D.; Swager, T. M. J. Org. Chem. 1999, 64, 6499-6504
55. To the best of our knowledge, the most similar oxa-cycloalkyne reported in the literature is the oxa-dibenzocyclooctyne prepared by photochemical decarbonylation of corresponding cyclopropenones: McNitt, C. D.; Popik, V. V. Org. Biomol. Chem. 2012, 10, 8200-8202
56. Yu, X.; Ding, Q.; Wang, W.; Wu, J. Tetrahedron Lett. 2008, 49, 4390-4393
57. Liu, L.-P.; Hammond, G. B. Org. Lett. 2010, 12, 4640-4643
58. Meth-Cohn, O.; Jiang, H. J. Chem. Soc., Perkin Trans. 1 1998, 3737-3742
59. Zhu, S.; Zhang, Z.; Huang, X.; Jiang, H.; Guo, Z. Chem. - Eur. J. 2013, 19, 4695-4700
60. Huang, Q.; Hunter, J. A.; Larock, R. C. J. Org. Chem. 2002, 67, 3437-3444
61. Castedo, L.; Guitian, E.; Pena, D.; Perez, D. Eur. J. Org. Chem. 2003, 1238-1243
62. Reddy, B. V. S.; Jalal, S.; Borkar, P.; Yadav, J. S.; Reddy, P. G.; Sarma, A. V. S. Tetrahedron Lett. 2013, 54, 1519-1523