Rhodium(III)-Catalyzed [3+2] Annulation of 5-Aryl-2,3-dihydro-1H-pyrroles with Internal Alkynes through C(sp2)-H/Alkene Functionalization

Angewandte Chemie - International Edition

Volumn 53, Issue 42, 2014, Pages 11338-11341

  Zhou, Ming Bo ^a   Pi, Rui ^a   Hu, Ming ^a   Yang, Yuan ^a   Song, Ren Jie ^a   Xia, Yuanzhi ^c   Li, Jin Heng ^a,b  

^a HUNAN UNIVERSITY   (China)

^b LANZHOU UNIVERSITY   (China)

^c WENZHOU UNIVERSITY   (China)

Author keywords

alkynes; annulation; heterocycles; rhodium; spiro compounds

Indexed keywords

CATALYSIS; HYDROCARBONS; RHODIUM;

ALKYNES; ANNULATION; FUNCTIONALIZATIONS; HETEROCYCLES; INTERNAL ALKYNES; PYRROLIDINES; RHODIUM (III); SPIRO COMPOUNDS;

RHODIUM COMPOUNDS;

ALKENE; ALKYNE; INDENE; INDENE DERIVATIVE; PYRROLE DERIVATIVE; PYRROLIDINE DERIVATIVE; RHODIUM; SPIRO COMPOUND;

CATALYSIS; CHEMISTRY;

ALKENES; ALKYNES; CATALYSIS; INDENES; PYRROLES; PYRROLIDINES; RHODIUM; SPIRO COMPOUNDS;

EID: 84907858332     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201407175     Document Type: Article

References (66)

1. "Preparation of amino-acid-linked spiroring compounds as hepatitis C virus (HCV) inhibitors":, Y. Zhang, J. Zhang, H. Xie, Q. Ren, X. Wu, H. Luo, C. Fu, B. Hu, S. Li, C. Tang, Y. Lei, Q. Yu, Q. Fang, C. Qang, PCT Int. Appl. WO 2014048072A1 20140403, 2014 [CAN 160:530540];
2. "Preparation of spiro-heterocyclic compounds as inhibitors of β-secretase":, L. W. Dillard, J. Yuan, K. Leftheris, S. Venkatraman, G. Wu, L. Jia, Z. Xu, S. Cacatian, A. Morales-Ramos, S. Singh, Y. Zheng, PCT Int. Appl. WO 2011106414A1 20110901, 2011 [CAN 155:380365];
3. P. Jimonet, A. Boireau, M. Chevé, D. Damour, A. Genevois-Borella, A. Imperato, J. Pratt, J. C. R. Randle, Y. Ribeill, J.-M. Stutzmann, S. Mignani, Bioorg. Med. Chem. Lett. 1999, 9, 2921;
4. T. Ullrich, S. Krich, D. Binder, K. Mereiter, D. J. Anderson, M. D. Meyer, M. Pyerin, J. Med. Chem. 2002, 45, 4047;
5. "Isonicotinic acid derivatives and related spirocompounds with herbicidal action and their preparation and compositions containing them":, H. R. Waespe, G. R. E. vanLommen, V. K. Sipido, PCT Int. Appl. WO 9209577A1 19920611, 1992 [CAN 117:191692];
6. W. W. Paudler, G. I. Kerley, J. McKay, J. Org. Chem. 1963, 28, 2194;
7. H. M. Kantarjian, M. Talpaz, V. Santini, A. Murgo, B. Cheson, S. M. O'Brien, Cancer 2001, 92, 1591;
8. S. Sacchi, H. M. Kantarjian, S. O'Brien, J. Cortes, M. B. Rios, F. J. Giles, M. Beran, C. A. Koller, M. J. Keating, M. Talpaz, Cancer 1999, 86, 2632;
9. V. I. Shifrin, P. Anderson, J. Biol. Chem. 1999, 274, 13985;
10. H. M. Kantarjian, M. Talpaz, V. Santini, A. Murgo, B. Cheson, S. M. O'Brien, Cancer 2001, 6, 1591;
11. V. Lévy, S. Zohar, C. Bardin, A. Vekhoff, D. Chaoui, B. Rio, O. Legrand, S. Sentenac, P. Rousselot, E. Raffoux, F. Chast, S. Chevret, J. P. Marie, Br. J. Cancer 2006, 95, 253.
12. For selected reviews, see:
13. L. Huang, in The Alkaloids, Vol.23 (Ed.:, A. Brossi,), Academic Press, New York, 1984, p. 157;
14. M. A. Jalil Miah, T. Hudlicky, J. W. Reed, in The Alkaloids, Vol.51 (Ed.:, A. Brossi,), Academic Press, New York, 1998, p. 199;
15. S. A. A. ElBialy, H. Braun, L. F. Tietze, Synthesis 2004, 2249.
16. Selected recent papers:
17. L. Planas, J. Pérard-Viret, J. Royer, J. Org. Chem. 2004, 69, 3087;
18. Q. Liu, E. M. Ferreira, B. M. Stoltz, J. Org. Chem. 2007, 72, 7352;
19. R. Sommerville, H. E. Rosenberg, P. A. Crooks, J. Pharm. Sci. 1985, 74, 553;
20. M. Li, F.-M. Gong, L.-R. Wen, Z.-R. Li, Eur. J. Org. Chem. 2011, 3482;
21. A. R. SureshBabu, D. Gavaskar, R. Raghunathan, J. Organomet. Chem. 2013, 745-746, 409;
22. N. Sirisha, R. Raghunathan, J. Chem. Pharm. Res. 2013, 5, 382;
23. R. Moreno-Fuquen, D. M. Soto, L. M. Jaramillo-Gõmez, J. Ellena, J. C. Tenorio, Acta Crystallogr. Sect. E 2013, 69, o 1192;
24. R. Cwiek, P. Niedziejko, Z. Kałuża, J. Org. Chem. 2014, 79, 1222.
25. For selected reviews, see:
26. Advances in Cycloaddition, Vols.1-6, JAI, Greenwich, CT, 1988 - 1999
27. W. Carruthers, Cycloaddition Reactions in Organic Synthesis, Tetrahedron Organic Chemistry Series, Pergamon, Elmsford, NY, 1990;
28. M. Lautens, W. Klute, W. Tam, Chem. Rev. 1996, 96, 49;
29. L. Yet, Chem. Rev. 2000, 100, 2963;
30. Cycloaddition Reactions in Organic Synthesis (Eds.:, S. Kobayashi, K.A. Jørgensen,), Wiley-VCH, Weinheim, 2002;
31. F. Lõpez, J. L. Mascareñas, Beilstein J. Org. Chem. 2011, 7, 1075;
32. K. E. O. Ylijoki, J. M. Stryker, Chem. Rev. 2013, 113, 2244.
33. For special reviews on the cycloaddition reaction involving the CH functionalization, see:
34. P. Thansandote, M. Lautens, Chem. Eur. J. 2009, 15, 5874;
35. T. Satoh, M. Miura, Synthesis 2010, 3395;
36. D. A. Colby, R. G. Bergman, J. A. Ellman, Chem. Rev. 2010, 110, 624;
37. T. Satoh, M. Miura, Chem. Eur. J. 2010, 16, 11212;
38. D. A. Colby, A. S. Tsai, R. G. Bergman, J. A. Ellman, Acc. Chem. Res. 2012, 45, 814;
39. P. B. Arockiam, C. Bruneau, P. H. Dixneuf, Chem. Rev. 2012, 112, 5879;
40. E. M. Simmons, J. F. Hartwig, Angew. Chem. Int. Ed. 2012, 51, 3066;
41. Angew. Chem. 2012, 124, 3120;
42. F. W. Patureau, J. Wencel-Delord, F. Glorius, Aldrichimica Acta 2012, 45, 31;
43. G. Song, F. Wang, X. Li, Chem. Soc. Rev. 2012, 41, 3651;
44. L. Ackermann, Acc. Chem. Res. 2014, 47, 281;
45. S. DeSarkar, W. Liu, S. I. Kozhushkov, L. Ackermann, Adv. Synth. Catal. 2014, 356, 1461.
46. For papers on rhodium-catalyzed [3+2] annulation with alkynes in the presence of oxidants:
47. T. Fukutani, N. Umeda, K. Hirano, T. Satoh, M. Miura, Chem. Commun. 2009, 5141;
48. F. W. Patureau, T. Besset, N. Kuhl, F. Glorius, J. Am. Chem. Soc. 2011, 133, 2154;
49. K. Muralirajan, K. Parthasarathy, C.-H. Cheng, Angew. Chem. Int. Ed. 2011, 50, 4169;
50. Angew. Chem. 2011, 123, 4255.
51. For papers on the [3+2] annulation of aryl carbonyl compounds and their derivatives with alkynes without oxidants using rhenium:
52. Y. Kuninobu, A. Kawata, K. Takai, J. Am. Chem. Soc. 2005, 127, 13498; copper:
53. E. J. Park, S. H. Kim, S. Chang, J. Am. Chem. Soc. 2008, 130, 17268; rhodium(I):
54. Z.-M. Sun, S.-P. Chen, P. Zhao, Chem. Eur. J. 2010, 16, 2619;
55. D. N. Tran, N. Cramer, Angew. Chem. Int. Ed. 2011, 50, 11098;
56. Angew. Chem. 2011, 123, 11294; rhodium(III):
57. II:
58. J. Zhang, A. Ugrinov, P. Zhao, Angew. Chem. Int. Ed. 2013, 52, 6681;
59. Angew. Chem. 2013, 125, 6813; iridium-catalyzed [3+2] annulation of ketimines with alkynes toward indenamine-based spirocycles:
60. M. Nagamoto, T. Nishimura, Chem. Commun. 2014, 50, 6274.
61. Within the annulation of alkenes with alkynes, the vinyl C-H functionalization generally takes place rather than the addition of the carbon-carbon π bonds:
62. K. Morimoto, K. Hirano, T. Satoh, M. Miura, J. Org. Chem. 2011, 76, 9548;
63. A. Seoane, N. Casanova, N. Quiñones, J. L. Mascareñas, M. Gulías, J. Am. Chem. Soc. 2014, 136, 834;
64. A. Seoane, N. Casanova, N. Quiñones, J. L. Mascareñas, M. Gulías, J. Am. Chem. Soc. 2014, 136, 7607.
65. Detailed data, including the deuterium-labelling experiments and an intermolecular kinetic isotope effect experiment (see SchemeS1 in the Supporting Information), the DFT calculations, the crystallographic data of 3 ah, 2D NMR spectra of the two isomers of 3 ah, and 2D NMR spectra of 3 ha, are summarized in the Supporting Information.
66. CCDC 971156 (3 ah) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.