Salicylic acids as readily available starting materials for the synthesis of meta-substituted biaryls

Chemical Communications

Volumn 51, Issue 15, 2015, Pages 3127-3130

  Luo, Junfei ^a,b   Preciado, Sara ^a   Larrosa, Igor ^b  

^a QUEEN MARY UNIVERSITY OF LONDON   (United Kingdom)

^b UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

3 ARYLPHENOL; LEAD; PHENOL DERIVATIVE; SALICYLIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; ARYLATION; CATALYSIS; CHEMICAL BOND; CHEMICAL STRUCTURE; DECARBOXYLATION; OXIDATION; PROTODECARBOXYLATION; STEREOSPECIFICITY; SUZUKI REACTION; SYNTHESIS;

EID: 84926483472     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c4cc09674f     Document Type: Article

References (66)

1. (a) J. Yamaguchi, A. D. Yamaguchi and K. Itami, Angew. Chem., Int. Ed., 2012, 51, 8960
2. (b) L. McMurray, F. O'Hara and M. J. Gaunt, Chem. Soc. Rev., 2011, 40, 1885
3. (c) C.-L. Sun, B.-J. Li and Z.-J. Shi, Chem. Rev., 2011, 111, 1293
4. (d) L. Ackermann, Chem. Rev., 2011, 111, 1315
5. (e) J. Wencel-Delord, T. Droge, F. Liu and F. Glorius, Chem. Soc. Rev., 2011, 40, 4740
6. (f) C. S. Yeung and V. M. Dong, Chem. Rev., 2011, 111, 1215
7. (g) Topics in Current Chemistry: C-H Activation, ed. J.-Q. Yu and Z. Shi, 1st edn, 2010, Springer, Berlin Heidelberg.
8. F. Julía-Hernández, M. Simonetti and I. Larrosa, Angew. Chem., Int. Ed., 2013, 52, 11458.
9. For reviews on ortho-arylation see: (a) P. B. Arockiam, C. Bruneau and P. H. Dixneuf, Chem. Rev., 2012, 112, 5879
10. (b) D. A. Colby, R. G. Bergman and J. A. Ellman, Chem. Rev., 2010, 110, 624
11. (c) T. W. Lyons and M. S. Sanford, Chem. Rev., 2010, 110, 1147
12. For selected examples (since 2013), see: (d) B. Punji, W. Song, G. A. Shevchenko and L. Ackermann, Chem. - Eur. J., 2013, 19, 10605
13. (e) B. Li, C. Darcel and P. H. Dixneuf, ChemCatChem, 2014, 6, 127
14. (f) R. K. Chinnagolla and M. Jeganmohan, Chem. Commun., 2014, 50, 2442
15. (g) Z. Fan, K. Wu, L. Xing, Q. Yao and A. Zhang, Chem. Commun., 2014, 50, 1682
16. (h) R. Feng, J. Yao, Z. Liang, Z. Liu and Y. Zhang, J. Org. Chem., 2013, 78, 3688
17. (i) D. Li, N. Xu, Y. Zhang and L. Wang, Chem. Commun., 2014, 50, 14862
18. (j) J.-H. Chu, H.-P. Huang, W.-T. Hsu, S.-T. Chen and M.-J. Wu, Organometallics, 2014, 33, 1190
19. (k) Z. Liang, J. Yao, K. Wang, H. Li and Y. Zhang, Chem. - Eur. J., 2013, 19, 16825
20. (l) Z. Liang, R. Feng, H. Yin and Y. Zhang, Org. Lett., 2013, 15, 4544
21. (m) L. C. M. Castro and N. Chatani, Chem. - Eur. J., 2014, 20, 4548
22. (n) C. Wan, J. Zhao, M. Xu and J. Huang, J. Org. Chem., 2014, 79, 4751
23. (o) W. H. Jeon, T. S. Lee, E. J. Kim, B. Moon and J. Kang, Tetrahedron, 2013, 69, 5152
24. (p) D. Li, N. Xu, Y. Zhang and L. Wang, Chem. Commun., 2014, 50, 14862
25. (q) L. Y. Chan, L. Cheong and S. Kim, Org. Lett., 2013, 15, 2186
26. (r) J. Han, P. Liu, C. Wang, Q. Wang, J. Zhang, Y. Zhao, D. Shi, Z. Huang and Y. Zhao, Org. Lett., 2014, 16, 5682
27. (s) J.-H. Chu, C.-C. Wu, D.-H. Chang, Y.-M. Lee and M.-J. Wu, Organometallics, 2013, 32, 272
28. (t) F. Yang, F. Song, W. Li, J. Lan and J. You, RSC Adv., 2013, 3, 9649
29. (u) Y. Aihara and N. Chatani, Chem. Sci., 2013, 4, 664
30. (v) P. B. Arockiam, C. Fischmeister, C. Bruneau and P. H. Dixneuf, Green Chem., 2013, 15, 67
31. (w) Z. Jiang, L. Zhang, C. Dong, X. Su, H. Li, W. Tang, L. Xu and Q. Fan, RSC Adv., 2013, 3, 1025
32. (x) C. Arroniz, A. Ironmonger, G. Rassias and I. Larrosa, Org. Lett., 2013, 15, 910.
33. For examples of meta-arylation see: (a) H.-X. Dai, G. Li, X.-G. Zhang, A. F. Stepan and J.-Q. Yu, J. Am. Chem. Soc., 2013, 135, 7567
34. (b) L. Wan, N. Dastbaravardeh, G. Li and J.-Q. Yu, J. Am. Chem. Soc., 2013, 135, 18056
35. (c) R. J. Phipps and M. J. Gaunt, Science, 2009, 323, 1593
36. (d) H. A. Duong, R. E. Gilligan, M. L. Cooke, R. J. Phipps and M. J. Gaunt, Angew. Chem., Int. Ed., 2011, 50, 463
37. (e) B. Chen, X.-L. Hou, Y.-X. Li and Y.-D. Wu, J. Am. Chem. Soc., 2011, 133, 7668.
38. For examples of para-arylation see: (a) X. Wang, D. Leow and J.-Q. Yu, J. Am. Chem. Soc., 2011, 133, 13864
39. (b) C.-L. Ciana, R. J. Phipps, J. R. Brandt, F.-M. Meyer and M. J. Gaunt, Angew. Chem., Int. Ed., 2011, 50, 458
40. (c) Z. Wu, F. Luo, S. Chen, Z. Li, H. Xiang and X. Zhou, Chem. Commun., 2013, 49, 7653.
41. (a) M. Imanishi, S. Itou, K. Washizuka, H. Hamashima, Y. Nakajima, T. Araki, Y. Tomishima, M. Sakurai, S. Matsui, E. Imamura, K. Ueshima, T. Yamamoto, N. Yamamoto, H. Ishikawa, K. Nakano, N. Unami, K. Hamada, Y. Matsumura, F. Takamura and K. Hattori, J. Med. Chem., 2008, 51, 4002
42. (b) L. Trinh, M. McCutchen, M. Bonner-Fraser, S. Fraser, L. Bumm and D. McCauley, Biotechniques, 2007, 42, 756
43. (c) M. Mor, S. Rivara, A. Lodola, P.V. Plazzi, G. Tarzia, A. Duranti, A. Tontini, G. Piersanti, S. Kathuria and D. Piomelli, J. Med. Chem., 2004, 47, 4998
44. (d) P. Zhou, Y. Li, Y. Fan, Z. Wang, R. Chopra, A. Olland, Y. Hu, R. L. Magolda, M. Pangalos, P. H. Reinhart, M. J. Turner, J. Bard, M. S. Malamas and A. J. Robichaud, Bioorg. Med. Chem. Lett., 2010, 20, 2326.
45. J. Luo, S. Preciado and I. Larrosa, J. Am. Chem. Soc., 2014, 136, 4109.
46. (a) H. Kolbe, Justus Liebigs Ann. Chem., 1860, 113, 125
47. (b) A. Lindsey and H. Jeskey, Chem. Rev., 1957, 57, 583.
48. (a) M. Komiyama and H. Hirai, J. Am. Chem. Soc., 1983, 105, 2018
49. (b) H. Wynberg, Chem. Rev., 1960, 60, 169
50. (c) U. N. Hofslokken and L. Skattebol, Acta Chem. Scand., 1999, 53, 258
51. (d) D. Chakraborty, R. R. Gowda and P. Malik, Tetrahedron Lett., 2009, 50, 6553.
52. G. H. Posner and K. A. Canella, J. Am. Chem. Soc., 1985, 107, 2571.
53. Y.-H. Zhang and J.-Q. Yu, J. Am. Chem. Soc., 2009, 131, 14654.
54. In contrast, PEPPSI-IPr mediated Negishi, Suzuki and Kumada cross-couplings on diiodo- and dibromo-benzenes have been shown to selectively lead to di-over mono-functionalization: I. Larrosa, C. Somoza, A. Banquy and S. Goldup, Org. Lett., 2011, 13, 146.
55. (a) O. Daugulis, H.-Q. Do and D. Shabashov, Acc. Chem. Res., 2009, 42, 1074
56. (b) O. Daugulis, Top. Curr. Chem., 2010, 292, 57
57. (c) K. M. Engle, T.-S. Mei, M. Wasa and J.-Q. Yu, Acc. Chem. Res., 2012, 45, 788.
58. C. Arroniz, J. G. Denis, A. Ironmonger, G. Rassias and I. Larrosa, Chem. Sci., 2014, 5, 3509.
59. (a) C. K.-F. Chiu, M. A. Berliner and Z. B. Li, in Comprehensive Organic Functional Group Transformations, ed. A. R. Katritzky and R. J. K. Taylor, 1995, Pergamon Press, New York, Vol. 2, ch. 2.13
60. (b) C. L. E. Broekkamp, D. Leysen, B. W. M. M. Peeters and R. M. Pinder, J. Med. Chem., 1995, 38, 4615
61. (c) M. Palucki, J. P. Wolfe and S. L. Buchwald, J. Am. Chem. Soc., 1997, 119, 3395.
62. (a) A. O. Adeniji, B. M. Twenter, M. C. Byrns, Y. Jin, M. Chen, J. D. Winkler and T. M. Penning, J. Med. Chem., 2012, 55, 2311
63. (b) A. S. Guram, R. A. Rennels and S. L. Buchwald, Angew. Chem., Int. Ed., 1995, 34, 1348
64. (c) M. S. Driver and J. F. Hartwig, J. Am. Chem. Soc., 1997, 119, 8232.
65. (a) C. Y. HO, US Pat., US 2009/0105288 A1, 2009
66. (b) N. Miyaura and A. Suzuki, Chem. Rev., 1995, 95, 2457.