Catalytic transformations involving the activation of sp2 carbon-oxygen bonds

Topics in Organometallic Chemistry

Volumn 44, Issue , 2013, Pages 35-54

  Tobisu, Mamoru ^a   Chatani, Naoto ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Amination; Carbon oxygen bond activation; Cross coupling; Nickel; Reductive deoxygenation; Ruthenium

Indexed keywords

EID: 84870603480     PISSN: 14366002     EISSN: None     Source Type: Book Series    
DOI: 10.1007/3418-2012-42     Document Type: Review

References (82)

1. Tsuji J (2004) Palladium reagents and catalysts. Wiley, Chichester 2. Miyaura N (ed) (2001) Top Curr Chem 219
2. de Meijere A, Diederich F (2004) Metal-catalyzed cross-coupling reactions, 2nd edn. Wiley, Weinheim
3. Surry DS, Buchwald SL (2008) Angew Chem Int Ed 120:6438
4. Hartwig JF (2008) Acc Chem Res 41:1534
5. Tyman JHP (1996) Synthetic and natural phenols. Elsevier, Amsterdam
6. Rappoport Z (ed) (2003) The chemistry of phenols. Wiley, Chichester
7. Ritter K (1993) Synthesis 735
8. Yu D-G, Li B-J, Shi Z-J (2010) Acc Chem Res 43:1486
9. Li B-J, Yu D-G, Sun C-L, Shi Z-J (2011) Chem Eur J 17:1728
10. Rosen BM, Quasdorf KW, Wilson DA, Zhang N, Resmerita A-M, Garg NK, Percec V (2011) Chem Rev 111:1346
11. Wenkert E, Michelotti EL, Swindell CS (1979) J Am Chem Soc 101:2246
12. Wenkert E, Michelotti EL, Swindell CS, Tingoli M (1984) J Org Chem 49:4894
13. Hayashi T, Katsuro Y, Kumada M (1980) Tetrahedron Lett 21:3915
14. Wenkert E, Ferreira VF, Michelotti EL, Tingoli M (1985) J Org Chem 50:719
15. Wadman S,Whitby R, Yeates C, Kocienski P, CooperK (1987) J ChemSoc Chem Commun 241
16. Whitby R, Yeates C, Kocienski P, Costello G (1987) J Chem Soc Chem Commun 429
17. Kocienski P, Dixon NJ, Wadman S (1988) Tetrahedron Lett 29:2353
18. Kocienski P, Wadmana S, Cooper K (1988) Tetrahedron Lett 29:2357
19. Kocienski P, Love C, Whitby R, Roberts DA (1988) Tetrahedron Lett 29:2867
20. Ducoux J-P, Le Me'nez P, Kunesch N, Kunesch G, Wenkert E (1990) Tetrahedron Lett 31:2595
21. Ducoux J-P, Le Me'nez P, Kunesch N, Kunesch G, Wenkert E (1992) Tetrahedron 48:6403
22. Tingoli M, Panunzi B, Santacroce F (1999) Tetrahedron Lett 40:9329
23. Johnstone RAW, McLean WN (1988) Tetrahedron Lett 29:5553
24. Brigas AF, Johnstone RAW (2000) Perkin 1:1735
25. Dankwardt JW (2004) Angew Chem Int Ed 43:2428
26. Fu GC (2008) Acc Chem Res 41:1555
27. Guan B-T, Xiang S-K, Wu T, Sun Z-P, Wang B-Q, Zhao, K-Q, Shi Z-J (2008) Chem Commun 1437
28. Guan B-T, Xiang S-K, Wang B-Q, Sun Z-P, Wang Y, Zhao K-Q, Shi Z-J (2008) J Am Chem Soc 130:3268
29. Taylor BLH, Swift EC, Waetzig JD, Jarvo ER (2011) J Am Chem Soc 133:389
30. Tobisu M, Shimasaki T, Chatani N (2008) Angew Chem Int Ed 47:4866
31. Shimasaki T, Konno Y, Tobisu M, Chatani N (2009) Org Lett 11:4890
32. Ishizu J, Yamamoto T, Yamamoto A (1976) Chem Lett 1091
33. Chatani N, Tatamidani H, Ie Y, Kakiuchi F, Murai S (2001) J Am Chem Soc 123:4849
34. Tatamidani H, Kakiuchi F, Chatani N (2004) Org Lett 6:3597
35. Tatamidani H, Yokota K, Kakiuchi F, Chatani N (2004) J Org Chem 69:5615
36. Quasdorf KW, Tian X, Garg NK (2008) J Am Chem Soc 130:14422
37. Guan B-T, Wang Y, Li B-J, Yu D-G, Shi Z-J (2008) J Am Chem Soc 130:14468
38. Sun CL, Wang Y, Zhou X, Wu ZH, Li BJ, Guan BT, Shi ZJ (2010) Chem Eur J 16:5844
39. Li Z, Zhang S-L, Fu Y, Guo Q-X, Liu L (2009) J Am Chem Soc 131:8815
40. Li B-J, Li Y-Z, Lu X-Y, Liu J, Guan B-T, Shi Z-J (2008) Angew Chem Int Ed 47:10124
41. Kocienski P, Dixon N (1989) Synlett 52
42. Pore'e F-H, Clavel A, Betzer J-F, Pancrazi A, Ardisson J (2003) Tetrahedron Lett 44:7553
43. Sengupta S, Leite M, Raslan DS, Quesnelle C, Snieckus V (1992) J Org Chem 57:4066
44. Yoshikai N, Matsuda H, Nakamura E (2009) J Am Chem Soc 131:9590
45. Quasdorf KW, Riener M, Petrova KV, Garg NK (2009) J Am Chem Soc 131:17748
46. Antoft-Finch A, Blackburn T, Snieckus V (2009) J Am Chem Soc 131:17750
47. Xu L, Li B-J, Wu Z-H, Lu X-Y, Guan B-T, Wang B-Q, Zhao K-Q, Shi Z-J (2010) Org Lett 12:884
48. Quasdorf KW, Antoft-Finch A, Liu P, Silberstein AL, Komaromi A, Blackburn T, Ramgren SD, Houk KN, Snieckus V, Garg NK (2011) JACS 133:6352
49. Molander GA, Beaumard F (2010) Org Lett 12:4022
50. Yu D-G, Li B-J, Zheng S-F, Guan B-T, Wang B-Q, Shi Z-J (2010) Angew Chem Int Ed 49:4566
51. Yu D-G, Shi Z-J (2011) Angew Chem Int Ed 50:7097
52. Tobisu M, Shimasaki T, Chatani N (2009) Chem Lett 38:710
53. Tobisu M, Yasutome A, Yamakawa K, Shimasaki T, Chatani N (2012) Tetrahedron 68:5157
54. Shimasaki T, Tobisu M, Chatani N (2010) Angew Chem Int Ed 49:2929
55. Mesganaw T, Silberstein AL, Ramgren SD, Nathel NFF, Hong X, Liu P, Garg NK (2011) Chem Sci 2:1766
56. Ducoux J-P, Le Me'nez P, Kunesch N, Wenkert E (1993) J Org Chem 58:1290
57. A ́ lvarez-Bercedo P, Martin R (2010) J Am Chem Soc 132:17352
58. Tobisu M, Yamakawa K, Shimasaki T, Chatani N (2011) Chem Commun 47:2946
59. Kelley P, Lin S, Edouard G, Day MW, Agapie T (2012) J Am Chem Soc 134:5480
60. Sergeev AG, Hartwig JF (2011) Science 332:439
61. Huang K, Yu D-G, Zheng S-F, Wu Z-H, Shi Z-J (2011) Chem Eur J 17:786
62. Muto K, Yamaguchi J, Itami K (2012) J Am Chem Soc 134:169
63. Ehle AR, Watson MP (2012) Org Lett 14:1202
64. Kakiuchi F, Usui M, Ueno S, Chatani N, Murai S (2004) J Am Chem Soc 126:2706
65. Murai S, Kakiuchi F, Sekine S, Tanaka Y, Kamatani A, Sonoda M, Chatani N (1993) Nature 366:529
66. Ueno S, Mizushima E, Chatani N, Kakiuchi F (2006) J Am Chem Soc 128:16516
67. Nichols JM, Bishop LM, Bergman RG, Ellman JA (2010) J Am Chem Soc 132:12554
68. Yu J-Y, Kuwano R (2009) Angew Chem Int Ed 48:7217
69. Lee HW, Kwong FY (2009) Synlett 3151
70. Yu J-Y, Shimizu R, Kuwano R (2010) Angew Chem Int Ed 49:6396
71. Tamura M, Kochi JK (1971) J Am Chem Soc 93:1487
72. Bolm C, Legros J, Le Paih J, Zani L (2004) Chem Rev 104:6217
73. Sherry BD, Furstner A (2008) Acc Chem Res 41:1500
74. Nakamura E, Yoshikai N (2010) J Org Chem 75:6061
75. Sun C-L, Li B-J, Shi Z-J (2010) Chem Rev 111:1293
76. Li B-J, Xu L, Wu Z-H, Guan B-T, Sun C-L, Wang B-Q, Shi Z-J (2009) J Am Chem Soc 131:14656
77. Matsuura Y, Tamura M, Kochi T, Sato M, Chatani N, Kakiuchi F (2007) J Am Chem Soc 129:9858
78. Kocien'ski PJ, Love CJ, Whitby RJ, Costello G, Roberts DA (1989) Tetrahedron 45:3839
79. Xiao B, Fu Y, Xu J, Gong T-J, Dai J-J, Yi J, Liu L (2010) J Am Chem Soc 132:468
80. Snieckus V (1990) Chem Rev 90:879
81. Chauder BA, Kalinin AV, Snieckus V (2001) Synlett 140
82. Silberstein AL, Ramgren SD, Garg NK (2012) Org Lett 14:3796