Room temperature nickel(II) complexes [(4-MeOC6H 4)Ni(PCy3)2OTs and Ni(PCy3) 2X2]-catalyzed cross-coupling reactions of aryl/alkenyl sulfonates with arylboronic acids

Advanced Synthesis and Catalysis

Volumn 353, Issue 11-12, 2011, Pages 2051-2059

  Xing, Chun Hui ^a   Lee, Jeng Ru ^a   Tang, Zhen Yu ^a   Zheng, Jin Rong ^a   Hu, Qiao Sheng ^a  

^a CITY UNIVERSITY OF NEW YORK   (United States)

Author keywords

alkenyl tosylates; aryl arenesulfonates; arylboronic acids; cross coupling; nickel(II) complexes

Indexed keywords

EID: 80051956307     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201100151     Document Type: Article

References (109)

1. For recent reviews of triflate chemistry, see
2. Z. Gilson, R. Larock, Chem. Rev. 2006, 106, 4644-4680
3. I. Baraznenok, V. Nenajdenko, E. Balenkova, Tetrahedron 2000, 56, 3077-3119.
4. For a thematic issue on cross-coupling reactions: Acc. Chem. Res. 2008, 41, 1439-1564.
5. Also see
6. N. Miyaura, Top. Curr. Chem. 2002, 219, 11-59
7. A. Suzuki, J. Organomet. Chem. 1999, 576, 147-168
8. A. F. Littke, G. C. Fu, Angew. Chem. 2002, 114, 4350-4386
9. Angew.Chem. Int. Ed. 2002, 41, 4176-4211
10. S. Diez-Gonzalez, N. Marion, S. P. Nolan, Chem. Rev. 2009, 109, 3612-3676
11. S. Darses, J. P. Genet, Chem. Rev. 2008, 108, 288-325
12. L. Yin, J. Liebscher, Chem. Rev. 2007, 107, 133-173.
13. V. Percec, J.-Y. Bae, D. H. Hill, J. Org. Chem. 1995, 60, 1060-1065.
14. The cross-coupling of one example of electron-deficient aryl tosylate with lithium arylborates was reported:, Y. Kobayashi, R. Mizojiri, Tetrahedron Lett. 1996, 37, 8531-8534.
15. D. Zim, V. R. Lando, J. Dupont, A. L. Monteiro, Org. Lett. 2001, 3, 3049-3051.
16. M. K. Lakshman, P. F. Thomson, M. A. Nuqui, J. H. Hilmer, N. Sevova, B. Boggess, Org. Lett. 2002, 4, 1479-1482.
17. For Suzuki-Miyaura coupling reactions involving aryl mesylates
18. M. Ueda, A. Saitoh, S. Oh-Tani, N. Miyaura, Tetrahedron 1998, 54, 13079-13086
19. W. K. Chow, C. M. So, C. P. Lau, F. Y. Kwong, J. Org. Chem. 2010, 75, 5109-5112. For Suzuki-Miyaura coupling reactions involving vinyl tosylates
20. J. Wu, Q. Zhu, L. Wang, R. Fathi, Z. Yang, J. Org. Chem. 2003, 68, 670-673
21. J. Wu, L. Wang, R. Fathi, Z. Yang, Tetrahedron Lett. 2002, 43, 4395-4397
22. M. A. Huffman, N. Yasuda, Synlett 1999, 471-473.
23. For other coupling reactions involving aryl arenesulfonates
24. A. H. Roy, J. F. Hartwig, J. Am. Chem. Soc. 2003, 125, 8704-8705
25. X. Huang, K. W. Anderson, D. Zim, L. Jiang, A. Klapars, S. L. Buchwald, J. Am. Chem. Soc. 2003, 125, 6653-6655
26. J. Wu, Y. Liao, Z. Yang, J. Org. Chem. 2003, 68, 3642-3645
27. A. Furstner, A. Leitner, M. Mendez, H. Krause, J. Am. Chem. Soc. 2002, 124, 13856-13863
28. C. Bolm, J. P. Hildebrand, J. Rudolph, Synthesis 2000, 911
29. B. C. Hamann, J. F. Hartwig, J. Am. Chem. Soc. 1998, 120, 7369-7370
30. F. Nagatsugi, K. Uemura, S. Nakashima, M. Minoru, S. Sasaki, Tetrahedron Lett. 1995, 36, 421-423
31. D. Badone, R. Cecchi, U. Guzzi, J. Org. Chem. 1992, 57, 6321-6323.
32. B. Bhayana, B. P. Fors, S. L. Buchwald, Org. Lett. 2009, 11, 3954-3957
33. R. H. Munday, J. R. Martinelli, S. L. Buchwald, J. Am. Chem. Soc. 2008, 130, 2754-2755
34. B. P. Fors, D. A. Watson, M. R. Biscoe, S. L. Buchwald, J. Am. Chem. Soc. 2008, 130, 13552-13554
35. T. Ikawa, T. E. Barder, M. R. Biscoe, S. L. Buchwald, J. Am. Chem. Soc. 2007, 129, 13001-13007
36. H. N. Ngyuen, X. Huang, S. L. Buchwald, J. Am. Chem. Soc. 2003, 125, 11818-11819.
37. J.-i. Kuroda, K. Inamoto, K. Hiroya, T. Doi, Eur. J. Org. Chem. 2009, 2251-2261
38. T. A. Butler, E. C. Swift, B. H. Lipshutz, Org. Biomol. Chem. 2008, 6, 19-25
39. B. H. Lipshutz, T. Butler, E. Swift, Org. Lett. 2008, 10, 697-700
40. D. A. Wilson, C. J. Wilson, B. M. Rosen, V. Percec, Org. Lett. 2008, 10, 4879-4882
41. V. Percec, G. M. Golding, J. Smidrkal, O. Weichold, J. Org. Chem. 2004, 69, 3447-3452.
42. C. M. So, C. P. Lau, A. S. C. Chan, F. Y. Kwong, J. Org. Chem. 2008, 73, 7731-7734
43. K. Suzuki, T. Sawaki, Y. Hori, T. Kobayashi, Synlett 2008, 1809-1812
44. L. Zhang, T. Meng, J. Wu, J. Org. Chem. 2007, 72, 9346-9348. Also see
45. C. M. So, C. P. Lau, F. Y. Kwong, Angew. Chem. 2008, 120, 8179-8183
46. Angew. Chem. Int. Ed. 2008, 47, 8059-8063.
47. J. Pschierer, H. Plenio, Eur. J. Org. Chem. 2010, 2934-2937
48. A. Klapers, K. R. Campos, C. Chen, R. P. Volante, Org. Lett. 2005, 7, 1185-1188
49. D. Steinhuebel, J. M. Baxter, M. Palucki, I. W. Davies, J. Org. Chem. 2005, 70, 10124-10127
50. J. M. Baxter, D. Steinhuebel, M. Palucki, I. W. Davies, Org. Lett. 2005, 7, 215-218.
51. A. T. Lindhardt, T. M. Gøgsig, T. Skrydstrup, J. Org. Chem. 2009, 74, 135-143
52. T. Ogata, J. F. Hartwig, J. Am. Chem. Soc. 2008, 130, 13848-13849
53. M. E. Limmert, A. H. Roy, J. F. Hartwig, J. Org. Chem. 2005, 70, 9364-9370
54. C.-Y. Gao, L.-M. Yang, J. Org. Chem. 2008, 73, 1624-1627
55. L. Zhang, J. Wu, J. Am. Chem. Soc. 2008, 130, 12250-12251
56. T. J. Korn, M. A. Schade, S. Wirth, P. Knochel, Org. Lett. 2006, 8, 725-728
57. T. M. Gøgsig, A. T. Lindhardt, T. Skrydstrup, Org. Lett. 2009, 11, 4886-4888
58. L. Ackermann, A. Althammer, Org. Lett. 2006, 8, 3457-3460
59. M. G. Organ, S. Avola, I. Dubovyk, N. Hadei, E. A. B. Kantchev, C. J. O'Brien, C. Valente, Chem. Eur. J. 2006, 12, 4749-4755.
60. L. Ackermann, A. Althammer, S. Fenner, Angew. Chem. 2009, 121, 207-210
61. Angew. Chem. Int. Ed. 2009, 48, 201-204
62. L. Zhang. J. Wu, Adv. Synth. Catal. 2008, 350, 2409-2413
63. C. Cai, N. R. Rivera, J. Balsells, R. R. Sidler, J. C. McWilliams, C. S. Shultz, Y. Sun, Org. Lett. 2006, 8, 5161-5164.
64. Q.-S. Hu, Y. Lu, Z.-Y. Tang, H.-B. Yu, J. Am. Chem. Soc. 2003, 125, 2856-2857.
65. Z.-Y. Tang, Q.-S. Hu, J. Am. Chem. Soc. 2004, 126, 3058-3059
66. Z.-Y. Tang, Q.-S. Hu, Adv. Synth. Catal. 2004, 346, 1635-1637.
67. 2X complexes (X=Br, Cl) as catalysts for the cross-coupling of aryl tosylates with arylboronic acids at 100 °C:, X.-H. Fan, L.-M. Yang, Eur. J. Org. Chem. 2010, 2457-2460.
68. For examples of pincer nickel(II) complexes as catalysts at elevated temperature, see
69. T. Tu, H. Mao, C. Herbert, M. Xu, K. H. Doetz, Chem. Commun. 2010, 7796-7798
70. J.-i. Kuroda, K. Inamoto, K. Hiroya, T. Doi, Eur. J. Org. Chem. 2009, 2251-2261.
71. For recent examples of Pd(0)- or Ni(0)-catalyzed cross-couplings of 4-p-toluenesulfonyl or 4-halocoumarins, see
72. L. Zhang, T. Meng, R. Fan, J. Wu, J. Org. Chem. 2007, 72, 7279-7286
73. J. Wu, L. Zhang, H.-G. Xia, Tetrahedron Lett. 2006, 47, 1525-1528
74. J. Wu, Z. Yang, J. Org. Chem. 2001, 66, 7875-7878
75. L. Schio, F. Chatreaux, M. Klich, Tetrahedron Lett. 2000, 41, 1543-1545
76. [8d,9c]
77. For Rh(I)-catalyzed Suzuki-Miyaura coupling reactions involving vinyl tosylates, see
78. J. Wu, L. Zhang, K. Gao, Eur. J. Org. Chem. 2006, 5260-5263
79. J. Wu, L. Zhang, Y. Luo, Tetrahedron Lett. 2006, 47, 6747-6750.
80. For recent examples of Pd(0)- or Ni(0)-catalyzed 4-substituted 2(5H)-furanone synthesis from 4-halo- or 4-sulfonylxoy-2(5H)-furanones, see
81. J. Wu, X. Sun, L. Zhang, Chem. Lett. 2005, 34, 796-797
82. J. Wu, Q. Zhu, L. Wang, R. Fathi, Z. Yang, J. Org. Chem. 2003, 68, 670-673
83. R. Rossi, F. Bellina, E. Raugei, Synlett 2000, 1749-1752
84. M.-L. Yao, M.-Z. Deng, J. Org. Chem. 2000, 65, 5034-5036
85. J. Boukouvalas, N. Lachance, M. Ouellet, M. Trudeau, Tetrahedron Lett. 1998, 39, 7665-7668.
86. For recent examples of cross-coupling reactions with other activated alkenyl tosylates as substrates
87. F. Bellina, C. Marchetti, R. Rossi, Eur. J. Org. Chem. 2009, 4685-4690
88. B. D. Gallagher, B. R. Taft, B. H. Lipshutz, Org. Lett. 2009, 11, 5374-5377.
89. 3-catalyzed Suzuki cross-coupling reactions of imidazolylsulfonates:, J. Albaneze-Walker, R. Raju, J. A. Vance, A. J. Goodman, M. R. Reeder, J. Liao, M. T. Maust, P. A. Irish, P. Espino, D. R. Andrews, Org. Lett. 2009, 11, 1463-1466.
90. 2-catalyzed Suzuki coupling reaction of aryl/alkenyl esters with arylboronic acids at elevated temperature, see
91. B.-T. Guan, Y. Wang, B.-J. Li, D.-G. Yu, Z.-J. Shi, J. Am. Chem. Soc. 2008, 130, 14468-14470
92. K. W. Quasdorf, X. Tian, N. K. Garg, J. Am. Chem. Soc. 2008, 130, 14422-14423
93. L. Xu, B.-J. Li, Z.-H. Wu, X.-Y. Lu, B.-T. Guan, B.-Q. Wang, K.-Q. Zhao, Z.-J. Shi, Org. Lett. 2010, 12, 884-887. For a highlight and a computational study, see
94. L. J. Gooßen, K. Gooßen, C. Stanciu, Angew. Chem. 2009, 121, 3621-3624
95. Angew. Chem. Int. Ed. 2009, 48, 3569-3571
96. Z. Li, S.-L. Zhang, Y. Fu, Q.-X. Guo, L. Liu, J. Am. Chem. Soc. 2009, 131, 8815-8823. Also see
97. M. Baghbanzadeh, C. Pilger, C. O. Kappe, J. Org. Chem. 2011, 76, 1507-1510.
98. For recent reviews on Ni-catalyzed coupling reactions
99. B. M. Rosen, K. W. Quasdorf, D. A. Wilson, N. Zhang, A.-M. Resmerita, N. K. Garg, V. Percec, Chem. Rev. 2011, 111, 1346-1416
100. D.-G. Yu, B.-J. Li, Z.-J. Shi, Acc. Chem. Res. 2010, 43, 1486-1495
101. B.-J.; Li, D.-G. Yu, C-L. Sun, Z.-J. Shi, Chem. Eur. J. 2011, 17, 1728-1759.
102. E. Alacid, C. Nájera, Adv. Synth. Catal. 2006, 348, 945-952.
103. J. Zhang, L. Zhao, M. Song, T. C. W. Mak, Y. Wu, J. Organomet. Chem. 2006, 691, 1301-1306.
104. C. M. So, C. P. Lau, F. Y. Kwong, Org. Lett. 2007, 9, 2795-2798.
105. C.-L. Deng, R.-J. Song, S.-M. Guo, Z.-Q. Wang, J.-H. Li, Org. Lett. 2007, 9, 5111-5114.
106. J. Jin, M.-M. Cai, J.-X. Li, Synlett 2009, 2534-2538.
107. J. L. Bolliger, C. M. Frech, Adv. Synth. Catal. 2010, 352, 1075-1080.
108. L. Wu, B.-L. Li, Y.-Y. Huang, H.-F. Zhou, Y.-M. He, Q.-H. Fan, Org. Lett. 2006, 8, 3605-3608.
109. C. A. Parrish, S. L. Buchwald, J. Org. Chem. 2001, 66, 3820-3827.