Indium(I)-mediated radical carbon-carbon bond-forming reaction in aqueous media

Synlett

Volumn , Issue 9, 2010, Pages 1341-1344

  Ueda, Masafumi ^a   Miyabe, Hideto ^b   Torii, Masafumi ^a   Kimura, Takahiro ^a   Miyata, Okiko ^a   Naito, Takeaki ^a  

^a KOBE PHARMACEUTICAL UNIVERSITY   (Japan)

^b HYOGO COLLEGE OF MEDICINE   (Japan)

Author keywords

Aqueous media; Copper(I) chloride; Domino reaction; Indium(I) chloride; Oxime ether; Radical addition

Indexed keywords

CARBON; COPPER CHLORIDE; INDIUM CHLORIDE;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL BOND; CHEMICAL REACTION KINETICS; ELECTRON TRANSPORT; RADICAL REACTION;

EID: 77953266193     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1219921     Document Type: Article

References (73)

1. For reviews, see:, Rowlands G J., Tetrahedron 2010 66 1593
2. Rowlands G J., Tetrahedron 2009 65 8603
3. Perchyonok V T., Lykakis I N., Curr. Org. Chem. 2009 13 573
4. Kargbo R B., Cook G R., Curr. Org. Chem. 2007 11 1287
5. Herreras C I., Yao X Q., Li Z P., Li C J., Chem. Rev. 2007 107 2546
6. Li C J., Chen L, Chem. Soc. Rev. 2006 35 68
7. Li C J., Chem. Rev. 2005 105 3095
8. Nair V, Ros S, Jayan C N., Pillia B S., Tetrahedron 2004 60 1959
9. Kobayashi S, Manabe K, Acc. Chem. Res. 2002 35 209
10. Li C J., Acc. Chem. Res. 2002 35 533
11. Li C J., Green Chem. 2002 4 1
12. Maher J P., Annu. Rep. Prog. Chem., Sect. A 2001 97 49
13. Yuang Y F., Cao Z, Hu A G., Wang J T., Chin. J. Org. Chem. 2000 20 269
14. Liao L A., Li Z M., Chin. J. Org. Chem. 2000 20 306
15. Li C.-J, Chan [nl]T.-H, Tetrahedron 1999 55 11149
16. Li C.-J, Tetrahedron 1996 52 5643
17. Cintas P, Synlett 1995 1087
18. Lubineau A, Ang J, Queneau Y, Synthesis 1994 741
19. Li C.-J, Chem. Rev. 1993 93 2023
20. Auge J, Lubin-Germain N, Uziel J, Synthesis 2007 1739
21. Loh T P., Chua G L., Chem. Commun. 2006 2739
22. Podlech J, Maier T C., Synthesis 2003 633
23. Ranu B C., Eur. J. Org. Chem. 2000 2347
24. Chauhan K K., Frost C G., J. Chem. Soc., Perkin Trans. 1 2000 3015
25. Qin Y.-Y, Yang Y.-Y, Qiu X.-L, Qing F.-L, Synthesis 2006 1475
26. Takami K, Mikami S, Yorimitsu H, Shinokubo H, Oshima K, Tetrahedron 2003 59 6627
27. Inoue K, Sawada A, Shibata I, Baba A, J. Am. Chem. Soc. 2002 124 906
28. For a review, see
29. Miyabe H, Naito T, Org. Biomol. Chem. 2004 2 1267
30. Miyabe H, Ueda M, Nishimura A, Naito T, Tetrahedron 2004 60 4227
31. Miyabe H, Ueda M, Nishimura A, Naito T, Org. Lett. 2002 4 131
32. Miyabe H, Nishimura A, Ueda M, Naito T, Chem. Commun. 2002 1454
33. Yanada R, Takemoto Y, J. Synth. Org. Chem. 2009 67 239
34. Yanada R, Obika S, Nishimori N, Yamauchi M, Takemoto Y, Tetrahedron Lett. 2004 45 2331
35. Yanada R, Koh Y, Nishimori N, Matsumura A, Obika S, Mitsuya H, Fujii N, Takemoto Y, J. Org. Chem. 2004 69 2417
36. Yanada R, Nishimori N, Matsumura A, Fujii N, Takemoto Y, Tetrahedron Lett. 2002 43 4585
37. Recently, the related indium(0)-mediated radical reactions were reported, see:, Sugi M, Sakuma D, Togo H, [nl]J. Org. Chem. 2003 68 7629
38. Jang D O., Cho D H., Synlett 2002 631
39. Huang T, Keh C C. K., Li C.-J, Chem. Commun. 2002 2440
40. The use of indium(III) chloride in atom-transfer cyclization, see:, Cook G R., Hayashi R, Org. Lett. 2006 8 1045
41. Yang Y.-S, Shen Z.-L, Loh T.-P, Org. Lett. 2009 11 1209
42. Shen Z L., Cheong H L., Loh T P., Chem. Eur. J. 2008 14 1875
43. Shen Z L., Yeo Y L., Loh T P., [nl]J. Org. Chem. 2008 73 3922
44. Shen Z.-L, Loh T.-P, Org. Lett. 2007 9 5413
45. The use of indium(I) salts has been less explored except for allylation, see:, Ranu B C., Mandal T, Tetrahedron Lett. 2006 47 2859
46. Babu S A., Yasuda M, Shibata I, Baba A, J. Org. Chem. 2005 70 10408
47. Peppe C R., dasChagas P, Synlett 2004 1187
48. Ranu B C., Mandal T, J. Org. Chem. 2004 69 5793
49. Ranu B C., Das A, Tetrahedron Lett. 2004 45 6875
50. Ranu B C., Mandal T, Synlett 2004 1239
51. Ranu B C., Mandal T, Samanta S, Org. Lett. 2003 5 1439
52. doR.Barros O S., Lang E S., deOliveira C A. F., Peppe C, Zeni G, Tetrahedron Lett. 2002 43 7921
53. Nbrega J A., Gonalves S M. C., Peppe C, Tetrahedron Lett. 2001 42 4745
54. Nbrega J A. S., Gonalves M C., Peppe C, Tetrahedron Lett. 2000 41 5779
55. The use of indium(I) salts as Lewis acid for activation of functional groups, see:, Mahesh M, Murphy J A., Wessel H P., J. Org. Chem. 2005 70 4118
56. Keh C C., Wei K C., Li C.-J, J. Am. Chem. Soc. 2003 125 4062
57. For reviews on radical reactions, see: In Radicals in Organic Synthesis Vol. 1 and 2 Renaud P Sibi M P. Wiley-VCH Weinheim 2001
58. Sibi M P., Manyem S, Zimmerman J, Chem. Rev. 2003 103 3263
59. Friestad G K., Tetrahedron 2001 57 5461
60. Miyabe H, Ueda M, Naito T, Synlett 2004 1140
61. Radical reactions in aqueous media, see:, Yamazaki O, Togo H, Nogami G, Yokoyama M, Bull. Chem. Soc. Jpn. 1997 70 2519
62. Yorimitsu H, Nakamura T, Shinokubo H, Oshima K, J. Org. Chem. 1998 63 8604
63. Nakamura T, Yorimitsu H, Shinokubo H, Oshima K, Synlett 1998 1351
64. Kita Y, Nambu H, Ramesh N G., Anikumar G, Matsugi M, Org. Lett. 2001 3 1157
65. Disproportionation of InX, see:, Peppe C, Tuck D G., Victoriano L, J. Chem. Soc., Dalton Trans. 1982 2165
66. 2 system, see:, Beck H P., Wilhelm D, Hartl-Gunselmann A, Z. Anorg. Allg. Chem. 1991 602 65
67. CuCl-mediated radical reactions, see:, Nagashima H, Wakamatsu H, Itoh K, Tomo Y, Tsuji J, Tetrahedron Lett. 1983 24 2395
68. Ooi T, Doda K, Sakai D, Maruoka K, Tetrahedron Lett. 1999 40 2133
69. Ueda M, Miyabe H, Nishimura A, Sugino H, Naito T, Tetrahedron: Asymmetry 2003 14 2857
70. Ueda M, Miyabe H, Sugino H, Naito T, Org. Biomol. Chem. 2005 3 1124
71. Ueda M, Miyabe H, Kimura T, Kondoh E, Naito T, Miyata O, Org. Lett. 2009 11 4632
72. Miyabe H, Ueda M, Naito T, Chem. Commun. 2000 2059
73. Ueda M, Miyabe H, Nishimura A, Miyata O, Takemoto Y, Naito T, Org. Lett. 2003 5 3835