Tandem cycloisomerization/Suzuki coupling of arylethynyl MIDA boronates

Tetrahedron

Volumn 67, Issue 24, 2011, Pages 4306-4312

  Chan, Julian M W ^a   Amarante, Giovanni W ^a   Toste, F Dean ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Electrophilic cyclization; Gold catalysis; Heterocycles; MIDA boronates; Suzuki coupling

Indexed keywords

ALKYNE; BORONIC ACID DERIVATIVE; N METHYLIMINODIACETIC ACID BORONIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; ISOMERIZATION; PRIORITY JOURNAL; SUZUKI REACTION;

EID: 79957533564     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.04.011     Document Type: Article

References (74)

1. L. De Luca, G. Nieddu, A. Porcheddu, and G. Giacomelli Curr. Med. Chem. 16 2009 1 20
2. S. Bräse, C. Gil, and K. Knepper Bioorg. Med. Chem. 10 2002 2415 2437
3. M. Mor, G. Spadoni, B. Di Giacomo, G. Diamantini, A. Bedini, G. Tarzia, P.V. Plazzi, S. Rivara, R. Nonno, V. Lucini, M. Pannacci, F. Fraschini, and B.M. Stankov Bioorg. Med. Chem. 10 2001 1045 1057
4. D.A. Horton, G.T. Bourne, and M.L. Smythe Chem. Rev. 103 2003 893 930
5. T.A. Engler, K.O. LaTessa, R. Iyengar, W. Chai, and K. Agrios Bioorg. Med. Chem. 4 1996 1755 1769
6. J.R. Dai, Y.F. Hallock, J.H. Cardellina, and M. Boyd J. Nat. Prod. 61 1998 351 353
7. M.N.C. Diyasena, S. Sotheeswaran, S. Surendrakumar, S. Balasubramanian, M. Bokel, and W. Kraus J. Chem. Soc., Perkin Trans. 1 1985 1807 1809
8. F.M. Dean J. ApSimon, The Total Synthesis of Natural Products Vol. 1 1973 Wiley New York, NY
9. A.R. Katritzky, J. Li, and C.V. Stevens J. Org. Chem. 60 1995 3401 3404
10. G.A. Kraus, and H. Guo Org. Lett. 10 2008 3061 3063
11. D.F. Taber, and W. Tian J. Am. Chem. Soc. 128 2006 1058 1059
12. Y.-Q. Fang, and M. Lautens Org. Lett. 7 2005 3549 3552
13. G.W. Gribble J. Chem. Soc., Perkin Trans. 1 7 2000 1045 1075
14. D. Yue, T. Yao, and R.C. Larock J. Org. Chem. 71 2006 62 69
15. M.P. Kumar, and R.-S. Liu J. Org. Chem. 71 2006 4951 4955
16. For examples of boron and silicon containing substrates in gold-catalyzed cycloisomerization reactions see:
17. S. Park, and D. Lee J. Am. Chem. Soc. 128 2006 10664 10665
18. W. Horino, M.R. Luzung, and F.D. Toste J. Am. Chem. Soc. 128 2006 11364 11365
19. T. Matsuda, S. Kadowaki, Y. Yamaguchi, and M. Murakami Chem. Commun. 2008 2744 2746
20. J.C.H. Lee, and D.G. Hall Tetrahedron Lett. 52 2011 321 324
21. E.P. Gillis, and M.D. Burke Aldrichimica Acta 42 2009 17 27
22. S.J. Lee, T.M. Anderson, and M.D. Burke Angew. Chem., Int. Ed. 49 2010 8860 8863
23. E.M. Woerly, A.H. Cherney, E.K. Davis, and M.D. Burke J. Am. Chem. Soc. 132 2010 6941 6943
24. G.R. Dick, D.M. Knapp, E.P. Gillis, and M.D. Burke Org. Lett. 12 2010 2314 2317
25. D.M. Knapp, E.P. Gillis, and M.D. Burke J. Am. Chem. Soc. 131 2009 6961 6963
26. J.R. Struble, S.J. Lee, and M.D. Burke Tetrahedron 66 2010 4710 4718
27. For recent relevant reviews on gold-catalysis see:
28. M. Bandini Chem. Soc. Rev. 40 2011 1358 1367
29. A. Corma, A. Leya-Perez, and M.A. Sbater Chem. Rev. 111 2011 1657 1712
30. P. de Mendoza, and A.M. Echavarren Pure Appl. Chem. 82 2010 801 820
31. N.D. Shapiro, and F.D. Toste Synlett 2010 675 691
32. A.M. Abu Sohel, and R.-S. Liu Chem. Soc. Rev. 38 2009 2269 2281
33. S.F. Kirsch Synthesis 2008 3183 3204
34. N.T. Patil, and Y. Yamamoto Chem. Rev. 108 2008 3395 3442
35. For related tandem cyclization/coupling processes, see:
36. M. Ishikura, N. Takahashi, K. Yamada, and R. Yanada Tetrahedron 62 2006 11580 11591
37. G. Zhu, X. Tong, J. Cheng, Y. Sun, D. Li, and Z. Zhang J. Org. Chem. 70 2005 1712 1717
38. G. Zhu, and Z. Zhang Org. Lett. 6 2004 4041 4044
39. W.S. Cheung, R.J. Patch, and M.R. Player J. Org. Chem. 70 2005 3741 3744
40. S. Thielges, E. Meddah, P. Bisseret, and J. Eustache Tetrahedron Lett. 45 2004 907 910
41. M.G. Kadieva, and E.T. Oganesyan Chem. Heterocycl. Compd. 33 1997 1245 1258
42. G.W. Gribble Contemp. Org. Synth. 1 1994 145 172
43. C. Praveen, C. Iyyappan, and P.T. Perumal Tetrahedron Lett. 51 2010 4767 4771
44. B. Gabriele, G. Salerno, A. Fazio, and R. Pitelli Tetrahedron 59 2003 6251 6259
45. K. Hiroya, R. Jouka, M. Kameda, A. Yasuhara, and T. Sakamoto Tetrahedron 57 2001 9697 9710
46. D. Solé, and O. Serrano J. Org. Chem. 75 2010 6267 6270
47. Q. Sun, X. Zhou, K. Islam, and D.J. Kyle Tetrahedron Lett. 42 2001 6495 6497
48. R. Mancuso, S. Mehta, B. Gabriele, G. Salerno, W.S. Jenks, and R.C. Larock J. Org. Chem. 75 2010 897 901
49. H. Kusama, T. Sawada, A. Okita, F. Shiozawa, and N. Iwasawa Org. Lett. 8 2006 1077 1079
50. F. Wang, Z. Miao, and R. Chen Org. Biomol. Chem. 7 2009 2848 2850
51. D. Yue, C.N. Della, and R.C. Larock J. Org. Chem. 71 2006 3381 3388
52. A.V. Butin, V.T. Abaev, V.V. Mel'chin, and A.S. Dmitriev Tetrahedron Lett. 46 2005 8439 8441
53. K. Villeneuve, and W. Tam Organometallics 26 2007 6082 6090
54. M. Movassaghi, and M.D. Hill Org. Lett. 10 2008 3485 3488
55. C.D. Gilmore, K.M. Allan, and B.M. Stoltz J. Am. Chem. Soc. 130 2008 1558 1559
56. B. Wang, B. Lu, Y. Jiang, Y. Zhang, and D. Ma Org. Lett. 10 2008 2761 2763
57. BW.-Q. Hui, and S. Chiba Org. Lett. 11 2009 729 732
58. Y.-N. Niu, Z.-Y. Yan, G.-L. Gao, H.-L. Wang, X.-Z. Shu, K.-G. Ji, and Y.-M. Liang J. Org. Chem. 74 2009 2893 2896
59. D. Fischer, H. Tomeba, N.K. Pahadi, N.T. Patil, Z. Huo, and Y. Yamamoto J. Am. Chem. Soc. 130 2008 15720 15725
60. Y.-Y. Yang, W.-G. Shou, Z.-B. Chen, D. Hong, and Y.-G. Wang J. Org. Chem. 73 2008 3928 3930
61. A. Kotera, J. Uenishi, and M. Uemura Tetrahedron Lett. 51 2010 1166 1169
62. M. Hellal, J.-J. Bourguignon, and F.J.-J. Bihel Tetrahedron Lett. 49 2008 62 65
63. N.T. Patil, and Y. Yamamoto J. Org. Chem. 69 2004 5139 5142
64. For examples of the use of this complex, see:
65. B.D. Sherry, and F.D. Toste J. Am. Chem. Soc. 126 2004 15978 15979
66. B.D. Sherry, L. Maus, B.N. Lafortezza, and F.D. Toste J. Am. Chem. Soc. 128 2006 8132 8133
67. R.L. LaLonde, W.E. Brenzovich Jr., D. Benitez, E. Tkatchouk, K. Kelley, W.A. Goddard III, and F.D. Toste Chem. Sci. 1 2010 226 233
68. For discussions of ligand effects on gold catalyzed reactions see:
69. H.G. Raubenheimer, and H. Schmidbaur S. Afr. J. Sci. 107 2011 32 44
70. D. Benitez, N.D. Shapiro, E. Tkatchouk, Y. Wang, W.A. Goddard III, and F.D. Toste Nat. Chem. 1 2009 482 486
71. D.J. Gorin, B.D. Sherry, and F.D. Toste Chem. Rev. 108 2008 3351 3378
72. A.N. Nesmeyanov, E.G. Perevalova, Y.T. Struchkov, M.Y. Antipin, K.I. Grandberg, and V.P. Dyadchenko J. Organomet. Chem. 201 1980 343 349
73. Y. Yang, V. Ramamoorthy, and P.R. Sharp Inorg. Chem. 32 1993 1946 1950
74. A.B. Pangborn, M.A. Giardello, R.H. Grubbs, R.K. Rosen, and F.J. Timmers Organometallics 15 1996 1518 1520