Nickel-catalyzed intramolecular C-H arylation using aryl pivalates as electrophiles

Tetrahedron

Volumn 69, Issue 27-28, 2013, Pages 5780-5790

  Wang, Jiayi ^a   Ferguson, Devin M ^a   Kalyani, Dipannita ^a  

^a ST OLAF COLLEGE   (United States)

Author keywords

Arylation; C H activation; C O electrophiles; Catalysis; Nickel

Indexed keywords

2 (2 TOLYLOXY)PHENYL PIVALATE; 2 (3 METHOXYPHENOXY)PHENYL PIVALATE; 2 (3 TRIFLUOROMETHYLPHENOXY)PHENYL PIVALATE; 2 (4 FLUOROPHENOXY)PHENYL PIVALATE; 2 (4 METHOXYPHENOXY)PHENYL PIVALATE; 2 (4 TOLYLOXY)PHENYL PIVALATE; 2 (NAPHTHALENE 2 YLOXY)PHENYL PIVALATE; 2 [(4 FLUOROPHENYL)(METHYL)AMINO]PHENYL PIVALATE; 2 [(4 METHOXYPHENYL)(METHYL)AMINO]PHENYL PIVALATE; 2 PHENOXY 4 (TRIFLUOROMETHYL)PHENYL PIVALATE; 2 PHENOXY 5 (TRIFLUOROMETHYL)PHENYL PIVALATE; 2 PHENOXYPHENYL PIVALATE; 4 METHOXY 2 PHENOXYPHENYL PIVALATE; DIBENZOFURAN DERIVATIVE; ELECTROPHILE; NICKEL; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CATALYSIS; PRIORITY JOURNAL;

EID: 84878511895     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2013.04.096     Document Type: Article

References (76)

1. K.B.G. Torsell Natural Product Chemistry 1983 Wiley Chichester, UK
2. R.H. Thomson The Chemistry of Natural Products 1985 Blackie and Son Glasgow, UK
3. O. Baudoin, and F. Gueritte Stud. Nat. Prod. Chem. 29 2003 335 418
4. W. Herz, G.W. Kirby, H. Falk, and R.E. Moore Progress in the Chemistry of Organic Natural Products Vol. 82 2001 Springer Vienna, Austria
5. M.C. Kozlowski, B.J. Morgan, and E.C. Linton Chem. Soc. Rev. 38 2009 3193 3207 and references therein
6. I. Cepanec Synthesis of Biaryls 2004 Elsevier San Diego, CA
7. J. Hassan, M. Sevignon, C. Gozzi, E. Schultz, and M. Lemaire Chem. Rev. 102 2002 1359 1469
8. J. Magano, and J.R. Dunetz Chem. Rev. 111 2011 2177 2250
9. D. Alberico, M.E. Scott, and M. Lautens Chem. Rev. 107 2007 174 238
10. F. Kakiuchi, and T. Kochi Synthesis 2008 3013 3039
11. G.P. McGlacken, and L.M. Bateman Chem. Soc. Rev. 38 2009 2447 2464
12. X. Chen, K.M. Engle, D.-H. Wang, and J.-Q. Yu Angew. Chem., Int. Ed. 48 2009 5094 5115
13. L. Ackermann, R. Vincente, and A.R. Kapdi Angew. Chem., Int. Ed. 48 2009 9792 9826
14. F. Bellina, and R. Rossi Tetrahedron 65 2009 10269 10310
15. T.W. Lyons, and M.S. Sanford Chem. Rev. 110 2010 1147 1169
16. O. Daugulis Top. Curr. Chem. 292 2010 57 84
17. G.P. Chiusoli, M. Catellani, M. Costa, E. Motti, N. Della Ca', and G. Maestri Coord. Chem. Rev. 254 2010 456 469
18. A.A. Kulkarni, and O. Daugulis Synthesis 2009 4087 4109
19. C.-L. Sun, B.-J. Li, and Z.-J. Shi Chem. Rev. 111 2011 1293 1394 and references therein
20. N. Yoshikai, S. Asako, T. Yamakawa, L. Ilies, and E. Nakamura Chem. - Asian. J. 6 2011 3059 3065
21. S.W. Liu, R. Chen, X.Y. Guo, H.Q. Yang, G.J. Deng, and C.J. Li Green Chem. 14 2012 1577 1580
22. L. Ilies, M. Kobayashi, A. Matsumoto, N. Yoshikai, and E. Nakamura Adv. Synth. Catal. 354 2012 593 596
23. N. Yoshikai Synlett 2011 1047 1051
24. C.T. To, T.L. Chan, B.Z. Li, Y.Y. Hui, T.S.Z.Y. Kwok, S.Y. Lam, and K.S. Chan Tetrahedron Lett. 52 2011 1023 1026
25. W. Liu, H. Cao, J. Xin, L.Q. Jin, and A.W. Lei Chem. - Eur. J. 17 2011 3588 3592
26. B. Li, Z.H. Wu, Y.F. Gu, C.L. Sun, B.Q. Wang, and Z.J. Shi Angew. Chem., Int. Ed. 50 2011 1109 1113
27. H. Hachiya, K. Hirano, T. Satoh, and M. Miura Org. Lett. 11 2009 1737 1740
28. J. Canivet, J. Yamaguchi, I. Ban, and K. Itami Org. Lett. 11 2009 1733 1736
29. M. Tobisu, I. Hyodo, and N. Chatani J. Am. Chem. Soc. 131 2009 12070 12071
30. O. Kobayashi, D. Uraguchi, and T. Yamakawa Org. Lett. 11 2009 2679 2682
31. H. Hachiya, K. Hirano, T. Satoh, and M. Miura ChemCatChem 2 2010 1403 1406
32. H. Hachiya, K. Hirano, T. Satoh, and M. Miura Angew. Chem., Int. Ed. 49 2010 2202 2205
33. D.M. Shacklady-McAtee, S. Dasgupta, and M.P. Watson Org. Lett. 13 2011 3490 3493
34. G. Xie, T. Li, X. Qu, and J. Mao J. Mol. Catal. A. 340 2011 48 52
35. O. Daugulis, H.-Q. Do, and D. Shabashov Acc. Chem. Res. 42 2009 1074 1086
36. M. Zhang Appl. Organomet. Chem. 24 2010 269 284
37. H. Cao, H.Y. Zhan, Y.G. Lin, X.L. Lin, Z.D. Du, and H.F. Jiang Org. Lett. 14 2012 1688 1691
38. M. Brenner, G. Mayer, A. Terpin, and W. Steglich Chem. - Eur. J. 3 1997 70 74
39. Y. Kametani, T. Satoh, M. Miura, and M. Nomura Tetrahedron Lett. 41 2000 2655 2658
40. O. Hara, T. Nakamura, F. Sato, K. Makino, and Y. Hamada Heterocycles 68 2006 1 4
41. A.C.F. Cruz, N.D. Miller, and M.C. Willis Org. Lett. 9 2007 4391 4393
42. J. Roger, and H. Doucet Org. Biomol. Chem. 6 2008 169 174
43. D.J. Schipper, M. El-Salfiti, C.J. Whipp, and K. Fagnou Tetrahedron 65 2009 4977 4983
44. L. Ackermann, A. Althammer, and R. Born Angew. Chem., Int. Ed. 45 2006 2619 2622
45. L. Ackermann, and M. Mulzer Org. Lett. 10 2008 5043 5045
46. L. Ackermann, A. Althammer, and S. Fenner Angew. Chem., Int. Ed. 48 2009 201 204
47. L. Ackermann, S. Barfuesser, and J. Pospech Org. Lett. 12 2010 724 726
48. L. Ackermann, and S. Fenner Chem. Commun. 2011 430 432
49. S. Fan, J. Yang, and X. Zhang Org. Lett. 13 2011 4374 4377
50. L. Ackermann, J. Pospech, and H.K. Potukuchi Org. Lett. 14 2012 2146 2149
51. J.W.W. Chang, E.Y. Chia, C.L.L. Chai, and J. Seayad Org. Biomol. Chem. 10 2012 2289 2299
52. C.S. Nervig, P.J. Waller, and D. Kalyani Org. Lett. 14 2012 4838 4841
53. D.-G. Yu, B.-J. Li, and Z.-J. Shi Acc. Chem. Res. 43 2010 1486 1495
54. B.M. Rosen, K.W. Quasdorf, D.A. Wilson, N. Zhang, A.-M. Resmerita, N.K. Garg, and V. Percec Chem. Rev. 111 2011 1346 1416
55. B.-J. Li, D.-G. Yu, C.-L. Sun, and Z.-J. Shi Chem. - Eur. J. 17 2011 1728 1759
56. M.B. Smith, and J. March March's Advanced Organic Chemistry 6th ed. 2007 John Wiley and Sons Hoboken, NJ 670
57. V. Snieckus Chem. Rev. 90 1990 879 933
58. For a recent example on Co-catalyzed direct arylation using C-O electrophiles see: W.F. Song, and L. Ackermann Angew. Chem., Int. Ed. 51 2012 8251 8254
59. K. Muto, J. Yamaguchi, and K. Itami J. Am. Chem. Soc. 134 2012 169 172
60. K. Amaike, K. Muto, J. Yamaguchi, and K. Itami J. Am. Chem. Soc. 134 2012 13573 13576
61. C. Wang, I. Piel, and F. Glorius J. Am. Chem. Soc. 131 2009 4194 4195
62. B. Xiao, T.-J. Gong, Z.-J. Liu, J.-H. Liu, D.-F. Luo, J. Xu, and L. Liu J. Am. Chem. Soc. 133 2011 9250 9253
63. L.-C. Campeau, M. Parisien, A. Jean, and K. Fagnou J. Am. Chem. Soc. 128 2006 581 590
64. C.-L. Campeau, M. Parisien, M. Lablanc, and K. Fagnou J. Am. Chem. Soc. 126 2004 9186 9187
65. L. Ackermann Chem. Rev. 111 2011 1315 1345
66. D. Lapointe, and K. Fagnou Chem. Lett. 39 2012 1118 1126
67. S. Gorelsky, D. Lapointe, and K. Fagnou J. Org. Chem. 77 2012 658 668
68. K.W. Quasdorf, X. Tian, and N.K. Garg J. Am. Chem. Soc. 130 2008 14422
69. K.W. Quasdorf, M. Riener, K.V. Petrova, and N.K. Garg J. Am. Chem. Soc. 131 2009 17747 17748
70. N. Jalalian, E.E. Ishikawa, L.F. Silva Jr., and B. Olofsson Org. Lett. 13 2011 1552 1555
71. Z. Du, J. Zhou, C. Si, and C.S. Weili Ma Synlett 2011 3023 3025
72. H.J. Kim, M. Kim, and S. Chang Org. Lett. 13 2011 2368 2371
73. B. Sreedhar, R. Arundhathi, P.L. Reddy, and M.L. Kantam J. Org. Chem. 74 2009 7951 7954
74. A.B. Naidu, E.A. Jaseer, and G. Sekar J. Org. Chem. 74 2009 3675 3679
75. J. Chen, X. Wang, X. Zheng, J. Ding, M. Liu, and H. Wu Tetrahedron 68 2012 8905 8907
76. J.W. Lockner, D.D. Dixon, R. Risgaard, and P.S. Baran Org. Lett. 13 2011 5628 5631