Regiocontroled palladium-catalysed direct arylation at carbon C2 of benzofurans using benzenesulfonyl chlorides as the coupling partners

ChemCatChem

Volumn 6, Issue 5, 2014, Pages 1303-1309

  Loukotova, Lenka ^a,b   Yuan, Kedong ^a   Doucet, Henri ^a  

^a INSTITUT DES SCIENCES CHIMIQUES DE RENNES   (France)

^b CHARLES UNIVERSITY   (Czech Republic)

Author keywords

arenes; C C coupling; halides; palladium; regioselectivity

Indexed keywords

CARBON; CATALYSIS; CHLORINE COMPOUNDS; METAL HALIDES; PALLADIUM; REGIOSELECTIVITY;

ARENES; ARYL HALIDES; ARYLATIONS; BENZOFURANS; C-C COUPLING; HALIDES; LOW COSTS; REGIO-SELECTIVE;

AROMATIC COMPOUNDS;

EID: 84900309962     PISSN: 18673880     EISSN: 18673899     Source Type: Journal    
DOI: 10.1002/cctc.201301077     Document Type: Article

References (86)

1. A. Ohta, Y. Akita, T. Ohkuwa, M. Chiba, R. Fukunaga, A. Miyafuji, T. Nakata, N. Tani, Y. Aoyagi, Heterocycles 1990, 31, 1951-1958.
2. D. Alberico, M. E. Scott, M. Lautens, Chem. Rev. 2007, 107, 174-238
3. T. Satoh, M. Miura, Chem. Lett. 2007, 36, 200-205
4. L.-C. Campeau, D. R. Stuart, K. Fagnou, Aldrichimica Acta 2007, 40, 35-41
5. I. V. Seregin, V. Gevorgyan, Chem. Soc. Rev. 2007, 36, 1173-1193
6. B.-J. Li, S.-D. Yang, Z.-J. Shi, Synlett 2008, 949-957
7. C. Lewis, R. G. Bergman, J. A. Ellman, Acc. Chem. Res. 2008, 41, 1013-1025
8. F. Bellina, R. Rossi, Tetrahedron 2009, 65, 10269-10310
9. L. Ackermann, R. Vicente, A. Kapdi, Angew. Chem. Int. Ed. 2009, 48, 9792-9826
10. Angew. Chem. 2009, 121, 9976-10011
11. X. Chen, K. M. Engle, D.-H. Wang, J.-Q. Yu, Angew. Chem. Int. Ed. 2009, 48, 5094-5115
12. Angew. Chem. 2009, 121, 5196-5217
13. O. Daugulis, H.-Q. Do, D. Skabashov, Acc. Chem. Res. 2009, 42, 1074-1086
14. L. Joucla, L. Djakovitch, Adv. Synth. Catal. 2009, 351, 673-714
15. C.-L. Sun, B.-J. Li, Z.-J. Shi, Chem. Commun. 2010, 46, 677-685
16. J. Roger, A. L. Gottumukkala, H. Doucet, ChemCatChem 2010, 2, 20-40
17. C. Fischmeister, H. Doucet, Green Chem. 2011, 13, 741-753
18. L. Ackermann, Chem. Rev. 2011, 111, 1315-1345
19. L. McMurray, F. O'Hara, M. J. Gaunt, Chem. Soc. Rev. 2011, 40, 1885-1898
20. N. Kuhl, M. N. Hopkinson, J. Wencel-Delord, F. Glorius, Angew. Chem. Int. Ed. 2012, 51, 10236-10254
21. Angew. Chem. 2012, 124, 10382-10401
22. J. Yamaguchi, A. D. Yamaguchi, K. Itami, Angew. Chem. Int. Ed. 2012, 51, 8960-9009
23. Angew. Chem. 2012, 124, 9092-9142
24. S. R. Neufeldt, M. S. Sanford, Acc. Chem. Res. 2012, 45, 936-946
25. J. Wencel-Delord, F. Glorius, Nat. Chem. 2013, 5, 369-375.
26. T. Okazawa, T. Satoh, M. Miura, M. Nomura, J. Am. Chem. Soc. 2002, 124, 5286-5287
27. S. Kirchberg, T. Vogler, A. Studer, Synlett 2008, 2841-2845
28. S. Yanagisawa, K. Ueda, H. Sekizawa, K. Itami, J. Am. Chem. Soc. 2009, 131, 14622-14623
29. I. Schnapperelle, S. Breitenlechner, T. Bach, Org. Lett. 2011, 13, 3640-3643
30. K. Funaki, T. Sato, S. Oi, Org. Lett. 2012, 14, 6186-6189
31. K. Si Larbi, H. Y. Fu, N. Laidaoui, K. Beydoun, M. Miloudi, D. El Abed, S. Djebbar, H. Doucet, ChemCatChem 2012, 4, 815-823
32. D.-T. D. Tang, K. D. Collins, F. Glorius, J. Am. Chem. Soc. 2013, 135, 7450-7453.
33. I. S. Mann, D. A. Widdowson, J. M. Clough, Tetrahedron 1991, 47, 7991-8000
34. Y. Aoyagi, T. Mizusaki, A. Hatori, T. Asakura, T. Aihara, S. Inaba, K. Hayatsu, A. Ohta, Heterocycles 1995, 41, 1077-1084
35. N. Joubert, M. Urban, R. Pohl, M. Hocek, Synthesis 2008, 1918-1932
36. G. A. Molander, B. Canturk, L. E. Kennedy, J. Org. Chem. 2009, 74, 973-980
37. S. Tanaka, D. Tanaka, A. Sugie, A. Mori, Tetrahedron Lett. 2012, 53, 1173-1176
38. N. Ortega, B. Beiring, S. Urban, F. Glorius, Tetrahedron 2012, 68, 5185-5192.
39. F. Mongin, A. Bucher, J.-P. Bazureau, O. Bayh, H. Awad, F. Trecourt, Tetrahedron Lett. 2005, 46, 7989-7992
40. S. Wunderlich, P. Knochel, Org. Lett. 2008, 10, 4705-4707
41. S. Tamba, Y. Okubo, S. Tanaka, D. Monguchi, A. Mori, J. Org. Chem. 2010, 75, 6998-7001.
42. B. Liégault, I. Petrov, S. I. Gorelsky, K. Fagnou, J. Org. Chem. 2010, 75, 1047-1060
43. N. S. Nandurkar, M. J. Bhanushali, M. D. Bhor, B. M. Bhanage, Tetrahedron Lett. 2008, 49, 1045-1048
44. S. Matsuda, M. Takahashi, D. Monguchi, A. Mori, Synlett 2009, 1941-1944.
45. H. A. Chiong, O. Daugulis, Org. Lett. 2007, 9, 1449-1451
46. F. Shibahara, E. Yamaguchi, T. Murai, Chem. Commun. 2010, 46, 2471-2473.
47. C. Colas, M. Goeldner, Eur. J. Org. Chem. 1999, 1357-1366
48. with arylboronic acids:, S.-D. Yang, C.-L. Sun, Z. Fang, B.-J. Li, Y.-Z. Li, Z.-J. Shi, Angew. Chem. Int. Ed. 2008, 47, 1473-1476
49. Angew. Chem. 2008, 120, 1495-1498.
50. T. A. Dwight, N. R. Rue, D. Charyk, R. Josselyn, B. DeBoef, Org. Lett. 2007, 9, 3137-3139
51. C.-Y. He, S. Fan, X. Zhang, J. Am. Chem. Soc. 2010, 132, 12850-12852
52. K. C. Pereira, A. L. Porter, S. Potavathri, A. P. LeBris, B. DeBoef, Tetrahedron 2013, 69, 4429-4435.
53. For intermolecular rhodium-catalysed oxidative arylation of benzofurans:, J. Wencel-Delord, C. Nimphius, H. Wang, F. Glorius, Angew. Chem. Int. Ed. 2012, 51, 13001-13005
54. Angew. Chem. 2012, 124, 13175-13180.
55. S. I. Gorelsky, Coord. Chem. Rev. 2013, 257, 153-164.
56. X. Zhao, E. Dimitrijevic, V. M. Dong, J. Am. Chem. Soc. 2009, 131, 3466-3467
57. X. Zhao, V. M. Dong, Angew. Chem. Int. Ed. 2011, 50, 932-934
58. Angew. Chem. 2011, 123, 962-964
59. For sulfonylations of quinolines using CuI as catalyst:, Z. Wu, H. Song, X. Cui, C. Pi, W. Du, Y. Wu, Org. Lett. 2013, 15, 1270-1273.
60. N. Kamigata, M. Yoshikawa, T. Shimizu, J. Fluorine Chem. 1998, 87, 91-95
61. D. A. Nagib, D. W. C. MacMillan, Nature 2011, 480, 224-228.
62. For a review on transition-metal-mediated C-S bond activation:, L. Wang, W. He, Z. Yu, Chem. Soc. Rev. 2013, 42, 599-621.
63. M. Miura, H. Hashimoto, K. Itoh, M. Nomura, Tetrahedron Lett. 1989, 30, 975-976
64. M. Miura, H. Hashimoto, K. Itoh, M. Nomura, J. Chem. Soc. Perkin Trans. 1 1990, 2207-2211.
65. S. R. Dubbaka, P. Vogel, J. Am. Chem. Soc. 2003, 125, 15292-15293
66. S. R. Dubbaka, P. Vogel, Org. Lett. 2004, 6, 95-98
67. S. R. Dubbaka, P. Vogel, Angew. Chem. Int. Ed. 2005, 44, 7674-7684
68. Angew. Chem. 2005, 117, 7848-7859.
69. M. Zhang, S. Zhang, M. Lui, J. Cheng, Chem. Commun. 2011, 47, 11522-11524.
70. K. Yuan, H. Doucet, Chem. Sci. 2014, 5, 392-396.
71. T. Miao, L. Wang, Adv. Synth. Catal. 2014, DOI
72. T. Cantat, E. Génin, C. Giroud, G. Meyer, A. Jutand, J. Organomet. Chem. 2003, 687, 365-376
73. M. Ionita, J. Roger, H. Doucet, ChemSusChem 2010, 3, 367-376
74. Doucet, ChemSusChem 2010, 3, 367-376.
75. L. Djakovitch, P. Rollet, Adv. Synth. Catal. 2004, 346, 1782-1792.
76. S. E. Denmark, R. C. Smith, W.-T. T. Chang, J. M. Muhuhi, J. Am. Chem. Soc. 2009, 131, 3104-3118.
77. J. Bonnamour, M. Piedrafita, C. Bolm, Adv. Synth. Catal. 2010, 352, 1577-1581.
78. L. M. Geary, P. G. Hultin, Org. Lett. 2009, 11, 5478-5481.
79. A. Fürstner, P. W. Davies, J. Am. Chem. Soc. 2005, 127, 15024-15025.
80. G. Vernin, S. Coen, J. Metzger, C. Parkanyi, J. Heterocycl. Chem. 1979, 16, 97-103.
81. J. Guillaumel, N. Boccara, P. Demerseman, R. Royer, J. P. Bideau, M. Cotrait, N. Platzer, J. Heterocycl. Chem. 1990, 27, 605-614.
82. G. W. Kabalka, L. Wang, R. M. Pagni, Tetrahedron 2001, 57, 8017-8028.
83. X. F. Duan, J. Zeng, Z.-B. Zhang, G.-F. Zi, J. Org. Chem. 2007, 72, 10283-10286.
84. N. Takeda, O. Miyata, T. Naito, Eur. J. Org. Chem. 2007, 1491-1509.
85. Z. Shen, V. M. Dong, Angew. Chem. Int. Ed. 2009, 48, 784-786
86. Angew. Chem. 2009, 121, 798-800.