Rhodium-catalyzed intramolecular hydroarylation of 1-halo-1-alkynes: Regioselective synthesis of semihydrogenated aromatic heterocycles

Chemistry - A European Journal

Volumn 20, Issue 1, 2014, Pages 317-322

  Murase, Hirohiko ^a   Senda, Kousuke ^a   Senoo, Masato ^a   Hata, Takeshi ^a   Urabe, Hirokazu ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

chromene; dihydroquinolines; heterocycles; hydroarylation; rhodium

Indexed keywords

CHROMENE; DIHYDROQUINOLINES; HETEROCYCLES; HYDROARYLATION; REGIO-SELECTIVE; REGIOSELECTIVE SYNTHESIS; RHODIUM-CATALYZED; SYNTHETIC APPLICATION;

AROMATIC COMPOUNDS; AROMATIZATION; CATALYSIS; ETHERS; REGIOSELECTIVITY;

RHODIUM;

ALKYNE; BENZOPYRAN DERIVATIVE; CHROMENE; COORDINATION COMPOUND; HETEROCYCLIC COMPOUND; QUINOLINE DERIVATIVE; RHODIUM;

ARTICLE; CATALYSIS; CHEMISTRY; DIHYDROQUINOLINES; HETEROCYCLES; HYDROARYLATION; HYDROGENATION; STEREOISOMERISM; SYNTHESIS;

CHROMENE; DIHYDROQUINOLINES; HETEROCYCLES; HYDROARYLATION; RHODIUM;

ALKYNES; BENZOPYRANS; CATALYSIS; COORDINATION COMPLEXES; HETEROCYCLIC COMPOUNDS; HYDROGENATION; QUINOLINES; RHODIUM; STEREOISOMERISM;

EID: 84891484157     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201303008     Document Type: Article

References (91)

1. Friedel-Crafts and Related Reactions, Vols. I-IV (Ed.:, G. A. Olah,), Wiley, New York, 1963 -1965
2. G. A. Olah, R. Krishnamurti, G. K. S. Prakash, in Comprehensive Organic Synthesis, Vol. 3 (Eds.:, B. M. Trost, I. Fleming,), Pergamon, Oxford, 1991, pp. 293-339
3. M. B. Smith, J. March, March's Advanced Organic Chemistry, 6th ed., Wiley, Hoboken, 2007, pp. 705-733
4. F. A. Carey, R. J. Sundberg, Advanced Organic Chemistry Part B, 5th ed., Springer, New York, 2007, pp. 1014-1025.
5. The Friedel-Crafts reaction of aromatic compounds with acetylenes was little documented at the outset:, V. Franzen, in Friedel-Crafts and Related Reactions, Vol. II, Part 1 (Ed.:, G. A. Olah,), Wiley, New York, 1964, pp. 413-416.
6. M. Bandini, E. Emer, S. Tommasi, A. Umani-Ronchi, Eur. J. Org. Chem. 2006, 3527-3544
7. C. Nevado, A. M. Echavarren, Synthesis 2005, 167-182
8. T. Kitamura, Eur. J. Org. Chem. 2009, 1111-1125
9. X. Wang, L. Zhou, W. Lu, Curr. Org. Chem. 2010, 14, 289-307
10. D. A. Capretto, Z. Li, C. He, in Handbook of Cyclization Reactions, Vol. 2 (Ed.:, S. Ma,), Wiley-VCH, Weinheim, 2010, pp. 991-1023
11. R. Hayashi, G. R. Cook, in Handbook of Cyclization Reactions, Vol. 2 (Ed.:, S. Ma,), Wiley-VCH, Weinheim, 2010, pp. 1025-1054.
12. J. P. Brand, J. Waser, Chem. Soc. Rev. 2012, 41, 4165-4179; for our reports on the synthetic applications of haloacetylenes, see
13. Y. Fukudome, H. Naito, T. Hata, H. Urabe, J. Am. Chem. Soc. 2008, 130, 1820-1821
14. M. Yamagishi, K. Nishigai, T. Hata, H. Urabe, Org. Lett. 2011, 13, 4873-4875
15. M. Yamagishi, J. Okazaki, K. Nishigai, T. Hata, H. Urabe, Org. Lett. 2012, 14, 34-37
16. M. Yamagishi, K. Nishigai, A. Ishii, T. Hata, H. Urabe, Angew. Chem. 2012, 124, 6577-6580
17. Angew. Chem. Int. Ed. 2012, 51, 6471-6474.
18. F. W. Patureau, J. Wencel-Delord, F. Glorius, Aldrichimica Acta 2012, 45, 31-41
19. C. Zhu, R. Wang, J. R. Falck, Chem. Asian J. 2012, 7, 1502-1514
20. Eds.:, H. M. L. Davies, J. Du Bois, J.-Q. Yu, Chem. Soc. Rev. 2011, 40, 1857-2038
21. T. Satoh, M. Miura, Chem. Eur. J. 2010, 16, 11212-11222
22. Ed.:, R. H. Crabtree, Chem. Rev. 2010, 110, 575-1211
23. V. Michelet, P. Y. Toullec, J.-P. Genêt, Angew. Chem. 2008, 120, 4338-4386
24. Angew. Chem. Int. Ed. 2008, 47, 4268-4315
25. J. C. Lewis, R. G. Bergman, J. A. Ellman, Acc. Chem. Res. 2008, 41, 1013-1025
26. Y. J. Park, J.-W. Park, C.-H. Jun, Acc. Chem. Res. 2008, 41, 222-234
27. Modern Rhodium-Catalyzed Organic Reactions (Ed.:, P. A. Evans,), Wiley-VHC, Weinheim, 2005
28. H. M. L. Davies, M. S. Long, Angew. Chem. 2005, 117, 3584-3586
29. Angew. Chem. Int. Ed. 2005, 44, 3518-3520
30. K. Fagnou, M. Lautens, Chem. Rev. 2003, 103, 169-196
31. H. M. L. Davies, R. E. J. Beckwith, Chem. Rev. 2003, 103, 2861-2903
32. P. Müller, C. Fruit, Chem. Rev. 2003, 103, 2905-2919
33. T. Hayashi, K. Yamasaki, Chem. Rev. 2003, 103, 2829-2844
34. V. Ritleng, C. Sirlin, M. Pfeffer, Chem. Rev. 2002, 102, 1731-1769; for our recent reports on Rh-catalyzed activation of acetylenes, see
35. D. Shikanai, H. Murase, T. Hata, H. Urabe, J. Am. Chem. Soc. 2009, 131, 3166-3167
36. Y. T. Oh, K. Senda, T. Hata, H. Urabe, Tetrahedron Lett. 2011, 52, 2458-2461.
37. V. Mamane, P. Hannen, A. Fürstner, Chem. Eur. J. 2004, 10, 4556-4575
38. G. Huang, B. Cheng, L. Xu, Y. Li, Y. Xia, Chem. Eur. J. 2012, 18, 5401-5415; an unsuccessful case was also mentioned, see
39. K. Komeyama, R. Igawa, K. Takaki, Chem. Commun. 2010, 46, 1748-1750; for the preparation of non-halogenated dihydroquinolines and chromenes via hydroarylation, see
40. S. J. Pastine, S. W. Youn, D. Sames, Org. Lett. 2003, 5, 1055-1058
41. B. Martín-Matute, C. Nevado, D. J. Cárdenas, A. M. Echavarren, J. Am. Chem. Soc. 2003, 125, 5757-5766
42. C. Nieto-Oberhuber, M. P. Muñoz, E. Buñuel, C. Nevado, D. J. Cárdenas, A. M. Echavarren, Angew. Chem. 2004, 116, 2456-2460
43. Angew. Chem. Int. Ed. 2004, 43, 2402-2406
44. R. Alajarín, C. Burgos, in Modern Heterocyclic Chemistry, Vol. 3 (Eds.:, J. Alvarez-Builla, J. J. Vaquero, J. Barluenga,), Wiley-VCH, Weinheim, 2011, pp. 1527-1570
45. J. A. Joule, K. Mills, Heterocyclic Chemistry, 5th ed., Wiley, Chichester, 2010, pp. 177-203
46. Comprehensive Heterocyclic Chemistry, Vol. 2 (Eds.:, A. R. Katritzky, C. W. Rees, A. J. Boulton, A. McKillop,), Pergamon, Oxford, 1984
47. C. Bhanja, S. Jena, S. Nayak, S. Mohapatra, Beilstein J. Org. Chem. 2012, 8, 1668-1694
48. J. Barluenga, F. Rodríguez, F. J. Fañanás, Chem. Asian J. 2009, 4, 1036-1048
49. V. V. Kouznetsov, Tetrahedron 2009, 65, 2721-2750
50. J. P. Michael, Nat. Prod. Rep. 2008, 25, 166-187
51. J. P. Michael, Nat. Prod. Rep. 2007, 24, 223-246
52. S. A. Yamashkin, E. A. Oreshkina, Chem. Heterocycl. Compd. 2006, 42, 701-718
53. V. V. Kouznetsov, J. Heterocycl. Chem. 2005, 42, 39-59
54. H. Water, J. Prakt. Chem. 1998, 340, 309-314
55. A. R. Katritzky, S. Rachwal, B. Rachwal, Tetrahedron 1996, 52, 15031-15070
56. O. Meth-Cohn, Heterocycles 1993, 35, 539-557.
57. J. J. Li, G. W. Gribble, Palladium in Heterocyclic Chemistry, Pergamon, Amsterdam, 2000
58. T. Liu, H. Fu, Synthesis 2012, 2805-2824
59. H. Li, C. C. C. J. Seechurn, T. J. Colacot, ACS Catal. 2012, 2, 1147-1164
60. S. M. Wong, C. M. So, F. Y. Kwong, Synlett 2012, 23, 1132-1153
61. K. C. Majumdar, S. Samanta, B. Sinha, Synthesis 2012, 44, 817-847
62. Ed.:, S. L. Buchwald, Acc. Chem. Res. 2008, 41, 1439-1564
63. E. A. B. Kantchev, C. J. O'Brien, M. G. Organ, Angew. Chem. 2007, 119, 2824-2870
64. Angew. Chem. Int. Ed. 2007, 46, 2768-2813
65. R. J. Lundgren, M. Stradiotto, Aldrichimica Acta 2012, 45, 59-65
66. D. Maiti, B. P. Fors, J. L. Henderson, Y. Nakamura, S. L. Buchwald, Chem. Sci. 2011, 2, 57-68
67. F. Monnier, M. Taillefer, Angew. Chem. 2008, 120, 3140-3143
68. Angew. Chem. Int. Ed. 2008, 47, 3096-3099
69. D. S. Surry, S. L. Buchwald, Angew. Chem. 2008, 120, 6438-6461
70. Angew. Chem. Int. Ed. 2008, 47, 6338-6361
71. M. C. Willis, Angew. Chem. 2007, 119, 3470-3472
72. Angew. Chem. Int. Ed. 2007, 46, 3402-3404
73. S. V. Ley, A. W. Thomas, Angew. Chem. 2003, 115, 5558-5607
74. Angew. Chem. Int. Ed. 2003, 42, 5400-5449
75. K. Kunz, U. Scholz, D. Ganzer, Synlett 2003, 2428-2439
76. D. Prim, J.-M. Campagne, D. Joseph, B. Andrioletti, Tetrahedron 2002, 58, 2041-2075
77. V. V. Grushin, H. Alper, in Activation of Unreactive Bonds and Organic Synthesis (Ed.:, S. Murai,), Springer, Berlin, 1999, pp. 193-226. For individual reactions in Scheme 3, see
78. Z. Liang, S. Ma, J. Yu, R. Xu, J. Org. Chem. 2007, 72, 9219-9224
79. G. Uray, A.-M. Kelterer, J. Hashim, T. N. Glasnov, C. O. Kappe, W. M. F. Fabian, J. Mol. Struct. 2009, 929, 85-96.
80. J. Santamaría, C. Valdés, in Modern Heterocyclic Chemistry, Vol. 3 (Eds.:, J. Alvarez-Builla, J. J. Vaquero, J. Barluenga,), Wiley-VCH, Weinheim, 2011, pp. 1631-1682
81. J. A. Joule, K. Mills, Heterocyclic Chemistry, 5th ed., Wiley, Chichester, 2010, pp. 205-207 and 229-247
82. P. J. Brogden, C. D. Gabbutt, J. D. Hepworth, in Comprehensive Heterocyclic Chemistry, Vol. 3 (Eds.:, A. R. Katritzky, C. W. Rees, A. J. Boulton, A. McKillop,), Pergamon, Oxford, 1984, pp. 573-645
83. G. P. Ellis, in Comprehensive Heterocyclic Chemistry, Vol. 3 (Eds.:, A. R. Katritzky, C. W. Rees, A. J. Boulton, A. McKillop,), Pergamon, Oxford, 1984, pp. 647-736
84. J. D. Hepworth, in Comprehensive Heterocyclic Chemistry, Vol. 3 (Eds.:, A. R. Katritzky, C. W. Rees, A. J. Boulton, A. McKillop,), Pergamon, Oxford, 1984, pp. 737-883
85. T. E.-S. Ali, M. A. Ibrahim, S. M. Abdel-Kariem, Phosphorus Sulfur Silicon Relat. Elem. 2009, 184, 2358-2392
86. S. B. Ferreira, F. de C. da Silva, A. C. Pinto, D. T. G. Gonzaga, V. F. Ferreira, J. Heterocycl. Chem. 2009, 46, 1080-1097
87. Y.-L. Shi, M. Shi, Org. Biomol. Chem. 2007, 5, 1499-1504
88. A. Lévai, T. Tímár, P. Sebök, T. Eszenyi, Heterocycles 2000, 53, 1193-1203
89. K. C. Majumdar, P. Biswas, Heterocycles 1999, 50, 1227-1267
90. Chemistry of Heterocyclic Compounds, Vol. 36 (Ed.:, G. P. Ellis,), Wiley, New York, 1981.
91. For a relevant note, see:, B. M. Trost, Acc. Chem. Res. 1990, 23, 34-42.