Cobalt-Catalyzed Cross-Benzannulation of Conjugated Enynes and Diynes

Journal of Organic Chemistry

Volumn 80, Issue 14, 2015, Pages 7311-7316

  Röse, Philipp ^a   Garcia, Carmen Carlota Magraner ^a   Pünner, Florian ^a   Harms, Klaus ^a   Hilt, Gerhard ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE REFINING; COBALT; REACTION KINETICS;

BENZANNULATION; BENZANNULATION REACTION; BENZENE DERIVATIVES; COBALT CATALYSIS; CONJUGATED ENYNES; PALLADIUM-CATALYZED; REGIOISOMERS; REGIOSPECIFIC CONTROL;

CATALYSIS;

ALKYNE DERIVATIVE; BENZENE DERIVATIVE; COBALT; ENYNES; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CONJUGATION; CROSS BENZANNULATION; CROSS COUPLING REACTION; DEBROMINATION; ELECTRON; ENANTIOSELECTIVITY; ISOMER; REACTION ANALYSIS;

EID: 84937597942     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/acs.joc.5b01198     Document Type: Article

References (57)

1. Tanaka, K. Transition-Metal-Mediated Aromatic Ring Construction, 1 st ed.; Tanaka, K., Ed.; Wiley: Hoboken, NJ, 2013.
2. Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1984, 23, 539-644
3. Schore, N. E. Chem. Rev. 1988, 88, 1081-1119
4. Trost, B. M. Science 1991, 254, 1471-1477
5. Weding, N.; Hapke, M. Chem. Soc. Rev. 2011, 40, 4525-4538
6. Domíniguez, G.; Pérez-Castells, J. Chem. Soc. Rev. 2011, 40, 3430-3444
7. Back, T. G.; Bethell, R. J.; Parvez, M.; Taylor, J. A.; Wehrli, D. J. Org. Chem. 1999, 64, 7426-7432
8. Bouillon, J. P.; Musyanovich, R.; Portella, C.; Shermolovich, Y. Eur. J. Org. Chem. 2001, 3625-3629
9. Gerster, H.; Espenlaub, S.; Maas, G. Synthesis 2006, 2251-2259
10. Hilt, G.; du Mesnil, F.-X. Tetrahedron Lett. 2000, 41, 6757-6761
11. Hilt, G.; Smolko, K. I. Angew. Chem., Int. Ed. 2003, 42, 2795-2797
12. Alonso, F.; Yus, M. Recent Res. Dev. Org. Chem. 1999, 3, 9
13. Hilt, G. Chem. Rec. 2014, 14, 386
14. Kurahashi, T. In Transition-Metal-Mediated Aromatic Ring Construction, 1 st ed.; Tanaka, K., Ed.; Wiley: Hoboken, NJ, 2013; p 323.
15. Hilt, G.; Pünner, F. In Transition-Metal-Mediated Aromatic Ring Construction, 1 st ed.; Tanaka, K., Ed.; Wiley: Hoboken, NJ, 2013; p 341.
16. Dunetz, J. R.; Danheiser, R. L. J. Am. Chem. Soc. 2005, 127, 5776-5777
17. Hayes, M. E.; Shinokubo, H.; Danheiser, R. L. Org. Lett. 2005, 7, 3917-3920
18. Austin, W. F.; Zhang, Y.; Danheiser, R. L. Org. Lett. 2005, 7, 3905-3908
19. Austin, W. F.; Zhang, Y.; Danheiser, R. L. Tetrahedron 2008, 64, 915-925
20. Ajaz, A.; Bradley, A. Z.; Burrell, R. C.; Li, W. H. H.; Daoust, K. J.; Boddington Bovee, L.; DiRico, K. J.; Johnson, R. P. J. Org. Chem. 2011, 76, 9320-9328
21. Mak, X. Y.; Crombie, A. L.; Danheiser, R. L. J. Org. Chem. 2011, 76, 1852-1873
22. Wessig, P.; Matthes, A.; Schilde, U.; Kelling, A. Eur. J. Org. Chem. 2013, 2123-2129
23. Haberhauer, G.; Gleiter, R.; Fabig, S. Org. Lett. 2015, 17, 1425-1428
24. Wessig, P.; Müller, G. Chem. Rev. 2008, 108, 2051-2063
25. Saito, S.; Salter, M. M.; Gevorgyan, V.; Tsuboya, N.; Tando, K.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 3970-3971
26. Saito, S.; Tsuboya, N.; Yamamoto, Y. J. Org. Chem. 1997, 62, 5042-5047
27. Weibel, D.; Gevorgyan, V.; Yamamoto, Y. J. Org. Chem. 1998, 63, 1217-1220
28. Gevorgyan, V.; Tando, K.; Uchiyama, N.; Yamamoto, Y. J. Org. Chem. 1998, 63, 7022-7025
29. Gevorgyan, V.; Yamamoto, Y. J. Organomet. Chem. 1999, 576, 232-247
30. Saito, S.; Tsuboya, N.; Chounan, Y.; Nogami, T.; Yamamoto, Y. Tetrahedron Lett. 1999, 40, 7529-7532
31. Saito, S.; Ohmori, O.; Yamamoto, Y. Org. Lett. 2000, 2, 3853-3855
32. Gevorgyan, V.; Zatolochnaya, O. V. In Transition-Metal-Mediated Aromatic Ring Construction, 1 st ed.; Tanaka, K., Ed.; Wiley: Hoboken, NJ, 2013; p 355.
33. Gevorgyan, V.; Takeda, A.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 11313-11314
34. Gevorgyan, V.; Sadayori, N.; Yamamoto, Y. Tetrahedron Lett. 1997, 38, 8603-8604
35. Takeda, A.; Ohno, A.; Kadota, I.; Gevorgyan, V.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 4547-4548
36. Gevorgyan, V.; Quan, G. L.; Yamamoto J. Org. Chem. 1998, 63, 1244-1247
37. Gevorgyan, V.; Takeda, A.; Homma, M.; Sadayori, N.; Radhakrishnan, U.; Yamamoto, Y. J. Am. Chem. Soc. 1999, 121, 6391-6402
38. Gevorgyan, V.; Quan, L. G.; Yamamoto, Y. J. Org. Chem. 2000, 65, 568-572
39. Saito, S.; Uchiyama, N.; Gevorgyan, V.; Yamamoto, Y. J. Org. Chem. 2000, 65, 4338-4341
40. Gevorgyan, V.; Tsuboya, N.; Yamamoto, Y. J. Org. Chem. 2001, 66, 2743-2746
41. Gevorgyan, V.; Radhakrishnan, U.; Takeda, A.; Rubina, M.; Rubin, M.; Yamamoto, Y. J. Org. Chem. 2001, 66, 2835-2841
42. Rubin, M.; Sromek, A. W.; Gevorgyan, V. Synlett 2003, 2262-2265
43. Rubin, M.; Conley, M.; Gevorgyan, V. J. Am. Chem. Soc. 2006, 128, 5818-5827
44. Zatolochnaya, O. V.; Galenko, A. V.; Gevorgyan, V. Adv. Synth. Catal. 2012, 354, 1149-1155
45. Zatolochnaya, O. V.; Gevorgyan, V. Org. Lett. 2013, 15, 2562-2565
46. Pünner, F.; Hilt, G. Chem. Commun. 2012, 48, 3617-3619
47. Röse, P.; Pünner, F.; Hilt, G.; Harms, K. Synlett 2013, 1101-1104
48. Tang, X.; Woodward, S.; Krause, N. Eur. J. Org. Chem. 2009, 2836-2844
49. Kang, B.; Lee, J. M.; Kwak, J.; Lee, Y. S.; Chang, S. J. Org. Chem. 2004, 69, 7611-7664
50. Harcken, C.; Brückner, R. New J. Chem. 2001, 25, 40-54
51. Cheng, J.-K.; Loh, T.-P. J. Am. Chem. Soc. 2015, 137, 42-45
52. Rubin, Y.; Knobler, C. B.; Diederich, F. J. Am. Chem. Soc. 1990, 112, 1607-1617
53. Merkul, E.; Urselmann, D.; Müller, T. J. J. J. Org. Chem. 2011, 238-242
54. Schmidt, R.; Thorwirth, R.; Szuppa, T.; Stolle, A.; Ondruschka, B.; Hopf, H. Chem.-Eur. J. 2011, 17, 8129-8138
55. Shi Shun, A. L. K.; Chernick, E. T.; Eisler, S.; Tykwinski, R. R. J. Org. Chem. 2003, 68, 1339-1347
56. Ting, S.; Schnabel, T.; Lysenko, S.; Brandhorst, K.; Tamm, M. Chem. Commun. 2013, 49, 7189-7191
57. Christensen, M. A.; Rimmen, M.; Nielsen, M. B. Synlett 2013, 24, 2715-2719