Iridium-catalyzed borylation of thiophenes: versatile, synthetic elaboration founded on selective C-H functionalization

Tetrahedron

Volumn 64, Issue 26, 2008, Pages 6103-6114

  Chotana, Ghayoor A ^a   Kallepalli, Venkata A ^a   Maleczka Jr , Robert E ^a   Smith III, Milton R ^a  

^a MICHIGAN STATE UNIVERSITY   (United States)

Author keywords

Borylation; Bromination; C H activation; Catalysis; Iridium; One pot reactions; Suzuki Miyaura cross coupling; Thiophenes

Indexed keywords

BORONIC ACID DERIVATIVE; CARBON; ESTER; HYDROGEN; IRIDIUM; THIOPHENE DERIVATIVE;

ARTICLE; BROMINATION; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; PRIORITY JOURNAL; SUZUKI REACTION; SYNTHESIS;

EID: 43849105598     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.02.111     Document Type: Article

References (70)

1. Huynh W.U., Dittmer J.J., and Alivisatos A.P. Science 295 (2002) 2425-2427
2. Li G., Shrotriya V., Huang J., Yao Y., Moriarty T., Emery K., and Yang Y. Nat. Mater. 4 (2005) 864-868
3. Street R.A. Nat. Mater. 5 (2006) 171-172
4. Fox K.A.A., and Chelliah R. Expert Opin. Drug Metab. Toxicol. 3 (2007) 621-631
5. Sperry J.B., and Wright D.L. Curr. Opin. Drug Discov. Dev. 8 (2005) 723-740
6. De Francesco R., and Migliaccio G. Nature 436 (2005) 953-960
7. Chauvette R.R., Flynn E.H., Jackson B.G., Lavagnino E.R., Morin R.B., Mueller R.A., Pioch R.P., Roeske R.W., Ryan C.W., Spencer J.L., and Van Heyningen E. J. Am. Chem. Soc. 84 (1962) 3401-3402
8. Volhard J., and Erdmann H. Ber. Dtsch. Chem. Ges. (1885) 454-455
9. Meyer V. Ber. Dtsch. Chem. Ges. (1885) 217-218
10. Volhard J. Justus Liebigs Ann. Chem. 267 (1892) 172-185
11. Thomas V. C. R. Hebd. Seances Acad. Sci. 146 (1908) 642-645
12. Gilman H., and Shirley D.A. J. Am. Chem. Soc. 71 (1949) 1870-1871
13. Snieckus V. Chem. Rev. 90 (1990) 879-933
14. Arroo R.R.J., Jacobs J., VanGestel J.A.M., Kenkel H., Jannink W., Croes A.F., and Wullems G.J. New Phytol. 135 (1997) 175-181
15. Mosurkal R., Kumar R., Bruno F.F., Nagarajan R., Samuelson L., and Kumar J. Pure Appl. Chem. 77 (2005) 263-272
16. Campos K.R. Chem. Soc. Rev. 36 (2007) 1069-1084
17. Seregin I.V., and Gevorgyan V. Chem. Soc. Rev. 36 (2007) 1173-1193
18. Wolfe J.P., and Thomas J.S. Curr. Org. Chem. 9 (2005) 625-655
19. Anderson K.W., Tundel R.E., Ikawa T., Altman R.A., and Buchwald S.L. Angew. Chem., Int. Ed. 45 (2006) 6523-6527
20. Fairlamb I.J.S. Chem. Soc. Rev. 36 (2007) 1036-1045
21. Alessi M., Larkin A.L., Ogilvie K.A., Green L.A., Lai S., Lopez S., and Snieckus V. J. Org. Chem. 72 (2007) 1588-1594
22. Kalinin V.N. Synthesis (1992) 413-432
23. Ishiyama T., Murata M., and Miyaura N. J. Org. Chem. 60 (1995) 7508-7510
24. Murata M., Watanabe S., and Masuda Y. J. Org. Chem. 62 (1997) 6458-6459
25. Murata M., Oyama T., Watanabe S., and Masuda Y. J. Org. Chem. 65 (2000) 164-168
26. Iverson C.N., and Smith III M.R. J. Am. Chem. Soc. 121 (1999) 7696-7697
27. Cho J.Y., Iverson C.N., and Smith III M.R. J. Am. Chem. Soc. 122 (2000) 12868-12869
28. Cho J.Y., Tse M.K., Holmes D., Maleczka Jr. R.E., and Smith III M.R. Science 295 (2002) 305-308
29. Tse M.K., Cho J.Y., and Smith III M.R. Org. Lett. 3 (2001) 2831-2833
30. Ishiyama T., Takagi J., Hartwig J.F., and Miyaura N. Angew. Chem., Int. Ed. 41 (2002) 3056-3058
31. Takagi J., Sato K., Hartwig J.F., Ishiyama T., and Miyaura N. Tetrahedron Lett. 43 (2002) 5649-5651
32. Ishiyama T., Takagi J., Yonekawa Y., Hartwig J.F., and Miyaura N. Adv. Synth. Catal. 345 (2003) 1103-1106
33. Miyaura, N.; Ishiyama, T. PCT Int. Appl. WO 2003074533, 2003, p 42.
34. Boller T.M., Murphy J.M., Hapke M., Ishiyama T., Miyaura N., and Hartwig J.F. J. Am. Chem. Soc. 127 (2005) 14263-14278
35. Paul S., Chotana G.A., Holmes D., Reichle R.C., Maleczka Jr. R.E., and Smith III M.R. J. Am. Chem. Soc. 128 (2006) 15552-15553
36. Christophersen C., Begtrup M., Ebdrup S., Petersen H., and Vedso P. J. Org. Chem. 68 (2003) 9513-9516
37. Chotana G.A., Rak M.A., and Smith III M.R. J. Am. Chem. Soc. 127 (2005) 10539-10544
38. Mertins K., Zapf A., and Beller M. J. Mol. Catal. A: Chem. 207 (2004) 21-25
39. Ishiyama T., Ishida K., Takagi J., and Miyaura N. Chem. Lett. (2001) 1082-1083
40. Shimada S., Batsanov A.S., Howard J.A.K., and Marder T.B. Angew. Chem., Int. Ed. 40 (2001) 2168-2171
41. Ishiyama T., Takagi J., Ishida K., Miyaura N., Anastasi N.R., and Hartwig J.F. J. Am. Chem. Soc. 124 (2002) 390-391
42. Ishiyama T., Sato K., Nishio Y., Saiki T., and Miyaura N. Chem. Commun. (2005) 5065-5067
43. Strotman N.A., Sommer S., and Fu G.C. Angew. Chem., Int. Ed. 46 (2007) 3556-3558
44. Denmark S.E., and Baird J.D. Chem.-Eur. J. 12 (2006) 4954-4963
45. Karlsson O. Synth. Commun. 11 (1981) 29-34
46. Meth-Cohn O., and Ashton M. Tetrahedron Lett. 41 (2000) 2749-2752
47. Highly selective functionalization of 3-methylthiophene by DoM typically requires a hindered electrophile trap. Recently it has been shown that LiTMP metalates the 5-position of 3-methyl thiophene with high selectivity:. Smith K., and Barratt M.L. J. Org. Chem. 72 (2007) 1031-1034
48. Lomas J.S., Lacroix J.C., and Vaissermann J. J. Chem. Soc., Perkin Trans. 2 (1999) 2001-2010
49. Espaze F., Hamon J., Hirbec H., Vignon J., and Kamenka J.-M. Eur. J. Med. Chem. 35 (2000) 323-331
50. Miyasaka M., and Rajca A. Synlett (2004) 177-181
51. Pham Chiem V., Macomber R.S., Mark Jr. H.B., and Zimmer H. J. Org. Chem. 49 (1984) 5250-5253
52. Frohlich H., and Kalt W. J. Org. Chem. 55 (1990) 2993-2995
53. Odom J.D., Moore T.F., Goetze R., Noeth H., and Wrackmeyer B. J. Organomet. Chem. 173 (1979) 15-32
54. Feng, S.; Maleczka, R. E., Jr.; Smith, M. R., III, in preparation.
55. Lawesson S.-O. Ark. Kemi. 11 (1957) 387-395
56. Kuivila H.G., Benjamin L.E., Price A.D., Polevy J.H., and Murphy C.J. J. Org. Chem. 27 (1962) 825-829
57. Szumigala R.H., Devine P.N., Gauthier D.R., and Volante R.P. J. Org. Chem. 69 (2004) 566-569
58. Carreno M.C., Ruano J.L.G., Sanz G., Toledo M.A., and Urbano A. J. Org. Chem. 60 (1995) 5328-5331
59. Gallant, M.; Lachance, N.; Labelle, M.; Zamboni, R.; Juteau, H.; Gareau, Y.; Lacombe, P. PCT Int. Appl. WO 2001081312, 2001, p 77.
60. Talley J.J., Bertenshaw S.R., Carter J.S., Collins P.W., Docter S., Graneto M.J., Isakson P.C., Lee L.F., Malecha J.W., Miyashiro J.M., Penning T.D., Rogers R.S., Rogier D.J., Yu S.S., Anderson G.D., Burton E.G., Cogburn J.N., Gregory S.A., Koboldt C.M., Perkins W.E., Seibert K., Veehuizen A.W., and Zhang Y.Y. Actual. Chim. Ther. 25 (1999) 123-134
61. Parham W.E., Nicholson I., and Traynelis V.J. J. Am. Chem. Soc. 78 (1956) 850-854
62. Almutairi A., Yoon K., Tham F., and Marsella M.J. Pure Appl. Chem. 78 (2006) 777-781
63. Sudarsanam, V.; Giordano, A.; Vasu, K. K.; Thakar, H. M.; Giri, R. S.; Yerande, S. G.; Inamdar, G. S. PCT Int. Appl. WO 2007118149, 2007, p 172.
64. Pillai A.D., Rathod P.D., Xavier F.P., Vasu K.K., Padh H., and Sudarsanam V. Bioorg. Med. Chem. 12 (2004) 4667-4671
65. Merola J.S., and Kacmarcik R.T. Organometallics 8 (1989) 778-784
66. Uson R., Oro L.A., and Cabeza J.A. Inorg. Synth. 23 (1985) 126-130
67. Barton T.J., and Hussmann G.P. J. Org. Chem. 50 (1985) 5881-5882
68. Liska R. Heterocycles 55 (2001) 1475-1486
69. Wu X.M., and Rieke R.D. J. Org. Chem. 60 (1995) 6658-6659
70. Wu R.L., Schumm J.S., Pearson D.L., and Tour J.M. J. Org. Chem. 61 (1996) 6906-6921