Chelation-assisted arylation via C-H bond cleavage

Topics in Organometallic Chemistry

Volumn 24, Issue , 2008, Pages 35-60

  Ackermann, Lutz ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

Arylation; Chelation; Palladium; Rhodium; Ruthenium

Indexed keywords

EID: 35248816863     PISSN: 14366002     EISSN: None     Source Type: Book Series    
DOI: 10.1007/3418_2007_062     Document Type: Article

References (142)

1. de Meijere A, Diederich F (2004) Metal-Catalyzed Cross-Coupling Reactions, 2nd edn. Wiley, Weinheim
2. Beller M, Bolm C (2004) Transition Metals for Organic Synthesis, 2nd edn. Wiley, Weinheim
3. Arndtsen BA, Bergman RG, Mobley TA, Peterson TH (1995) Acc Chem Res 28:154
4. Shilov AE, Shul'pin GB (1997) Chem Rev 97:2879
5. Ritleng V, Sirlin C, Pfeffer M (2002) Chem Rev 102:1731-1769
6. Kakiuchi F, Chatani N (2003) Adv Synth Catal 345:1077-1101
7. Dyker G (2005) Handbook of C-H Transformations. Wiley, Weinheim
8. Godula K, Sames D (2006) Science 312:67
9. Alberico D, Scott ME, Lautens M (2007) Chem Rev 107:174
10. Fujita K-I, Nonogawa M, Yamaguchi R (2004) Chem Commun p 1926
11. Campeau L-C, Parisien M, Leblanc M, Fagnou K (2004) J Am Chem Soc 126:9186
12. Huang Q, Fazio A, Dai G, Campo MA, Larock RC (2006) J Am Chem Soc 128:7460
13. Bringmann G, Ochse M, Götz R (2000) J Org Chem 65:2069
14. Dyker G (1994) Angew Chem, Int Ed Engl 33:103
15. Dyker G (1992) Angew Chem, Int Ed Engl 31:1023
16. Campeau L-C, Fagnou K (2006) Chem Commun p 1253
17. Hassan J, Sevignon M, Gozzi C, Schulz E, Lemaire M (2002) Chem Rev 102:1359
18. Deprez NR, Kalyani D, Krause A, Sanford M (2006) J Am Chem Soc 128:4972
19. Bellina F, Cauteruccio S, Rossi R (2006) Eur J Org Chem p 1379
20. Lane BS, Brown MA, Sames D (2005) J Am Chem Soc 127:8050
21. Yokooji A, Satoh T, Miura M, Nomura M (2004) Tetrahedron 60:6757
22. Park C-H, Ryabova V, Seregin IV, Sromek AW, Gevorgyan V (2004) Org Lett 6:1159
23. Lane BS, Sames D (2004) Org Lett 6:2897
24. Li W, Nelson DP, Jensen MS, Noerrner RS, Javadi GJ, Cai D, Larsen RD (2003) Org Lett 5:4835
25. Yokooji A, Okazawa T, Satoh T, Miura M, Nomura M (2003) Tetrahedron Lett 59:5685
26. Mori A, Sekiguchi A, Masui K, Shimada T, Horie M, Osakada K, Kawamoto M, Ikeda T (2003) J Am Chem Soc 125:1700
27. McClure MS, Glover B, McSorley E, Millar A, Osterhout MH, Roschangar F (2001) Org Lett 3:1677
28. Kondo Y, Komine T, Sakamoto T (2000) Org Lett 2:3111
29. Pivsa-Art S, Satoh T, Kawamura Y, Miura M, Nomura M (1998) Bull Chem Soc Jpn 71:467
30. Akita Y, Itagaki Y, Takizawa S, Ohta A (1989) Chem Pharm Bull 37:1477
31. Miura M, Satoh T (2005) In: Tsuji J (ed) Top Organomet Chem, vol 14. Springer, Berlin Heidelberg New York, p 55
32. Miura M, Satoh T (2005) In: Dyker G (ed) Handbook of C-H Transformations. Wiley, Weinheim, p 229
33. Lewis JC, Wiedemann SH, Bergman RG, Ellman JA (2004) Org Lett 6:35
34. Wang X, Lane BS, Sames D (2005) J Am Chem Soc 127:4996
35. Lewis JC, Wu JY, Bergman RG, Ellman JA (2006) Angew Chem Int Ed 45:1589
36. Yanagisawa S, Sudo T, Noyori R, Itami K (2006) J Am Chem Soc 128:11748
37. Wiedemann SH, Ellman JA, Bergman RG (2005) In: Dyker G (ed) Handbook of C-H Transformations. Wiley, Weinheim, p 187
38. Catellani M (2005) In: Tsuji J (ed) Top Organomet Chem, vol 14. Springer, Berlin Heidelberg New York, p 21
39. Catellani M, Motti E (2005) In: Dyker G (ed) Handbook of C-H Transformations. Wiley, Weinheim, p 245
40. Faccini F, Motti E, Catellani M (2004) J Am Chem Soc 126:78
41. Cárdenas DJ, Martin-Matute B, Echavarren AM (2006) J Am Chem Soc 128:5033
42. Catellani M, Chiusoli GP (1985) J Organomet Chem 286:C13
43. Catellani M, Chiusoli GP, Castagnoli C (1991) J Organomet Chem 407:C30
44. Reiser O, Weber M, de Meijere A (1989) Angew Chem Int Ed Engl 28:1037
45. Albrecht K, Reiser O, Weber M, Knieriem B, de Meijere A (1994) Tetrahedron 50:383
46. Omae I (2004) Coord Chem Rev 248:995
47. Zhang X, Kanzelberger M, Emge TJ, Goldman AS (2004) J Am Chem Soc 126:13192
48. Lewis LN, Smith JF (1986) J Am Chem Soc 108:2728
49. Carrión MC, Cole-Hamilton DJ (2006) Chem Commun p 4527
50. Murai S, Kakiuchi F, Sekine S, Tanaka Y, Kamatani A, Sonoda M, Chatani N (1993) Nature 366:529
51. Kakiuchi F, Murai S (2002) Acc Chem Res 35:826
52. Forrest J (1960) J Chem Soc p 566
53. Björklund C, Nilsson M (1968) Acta Chem Scand 22:2338
54. Anctil EJ-G, Sniekus V (2004) In: De Meijere A, Diederich F (eds) Metal-Catalyzed Cross- Coupling Reactions. Wiley, Weinheim, p 761
55. Zaitsev VG, Daugulis O (2005) J Am Chem Soc 127:4156
56. Cope AC, Siekman RW (1965) J Am Chem Soc 87:3272
57. Louie J, Hartwig JF (1996) Angew Chem Int Ed Engl 35:2359
58. Garcia-Cuadrado D, Braga AAC, Maseras F, Echavarren AM (2006) J Am Chem Soc 128:1066
59. Harayama T, Kawata Y, Nagura C, Sato T, Miyagoe T, Abe H, Takeuchi Y (2005) Tetrahedron Lett 46:6091
60. Gozzi C, Lavenot L, Ilg K, Penalva V, Lemaire M (1997) Tetrahedron Lett 38:8867
61. Lavenot L, Gozzi C, Ilg K, Orlova I, Penalva V, Lemaire M (1998) J Organomet Chem 567:49
62. Borghese A, Geldhof G, Antoine L (2006) Tetrahedron Lett 47:9249
63. Glover B, Harvey KA, Liu B, Sharp MJ, Tymoschenko MF (2003) Org Lett 5:301
64. Okazawa T, Satoh T, Miura M, Nomura M (2002) J Am Chem Soc 124:5286
65. Satoh T, Kawamura Y, Miura M, Nomura M (1997) Angew Chem Int Ed Engl 36:1740
66. Satoh T, Miura M, Nomura M (2002) J Organomet Chem 653:161
67. Miura M, Satoh T (2005) In: Dyker G (ed) Handbook of C-H Transformations. Wiley, Weinheim, p 223
68. Kawamura Y, Satoh T, Miura M, Nomura M (1999) Chem Lett p 961
69. Kametani Y, Satoh T, Miura M, Nomura M (2000) Tetrahedron Lett 41:2655
70. Terao Y, Kametani Y, Wakui H, Satoh T, Miura M, Nomura M (2001) Tetrahedron 57:5967
71. Satoh T, Kametani Y, Terao Y, Miura M, Nomura M (1999) Tetrahedron Lett 40:5345
72. Gürbüz N, Özdemir I, Çetinkaya B (2005) Tetrahedron Lett 46:2273
73. Özdemir I, Demir S, Çetinkaya B (2005) Tetrahedron 61:9791
74. Terao Y, Wakui H, Satoh T, Miura M, Nomura M (2001) J Am Chem Soc 123:10407
75. Terao Y, Wakui H, Nomoto M, Satoh T, Miura M, Nomura M (2003) J Org Chem 68:5236
76. Nakano M, Satoh T, Miura M (2006) J Org Chem 71:8309
77. Gooßen LJ, Deng G, Levy LM (2006) Science 313:662
78. Forgione P, Brochu M-C, St-Onge M, Thesen KH, Bailey MD, Bilodeau F (2006) J Am Chem Soc 128:11350
79. Jun C-H (2004) Chem Soc Rev 33:610
80. Lafrance M, Rowley CN, Woo TK, Fagnou K (2006) J Am Chem Soc 128:8754
81. Lafrance M, Shore D, Fagnou K (2006) Org Lett 8:5097
82. Campeau L-C, Parisien M, Jean A, Fagnou K (2006) J Am Chem Soc 128:581
83. Kalyani D, Deprez NR, Desai LV, Sanford MS (2005) J Am Chem Soc 127:7330
84. Hull KL, Anani WQ, Sanford MS (2006) J Am Chem Soc 128:7134
85. Dick AR, Kampf JW, Sanford MS (2005) J Am Chem Soc 127:12790
86. Desai LV, Hull KL, Sanford MS (2004) J Am Chem Soc 126:9542
87. Dick AR, Hull KL, Sanford MS (2004) J Am Chem Soc 126:2300
88. Dick AR, Sanford MS (2006) Tetrahedron 62:2439
89. Canty AJ, Patel J, Rodemann T, Ryan JH, Skelton BW, White AH (2004) Organometallics 23:3466
90. Horino H, Inoue N (1981) J Org Chem 46:4416
91. Tremont SJ, Rahmen H (1984) J Am Chem Soc 106:5759
92. Chen X, Li J-J, Hao X-S, Goodhue CE, Yu J-Q (2006) J Am Chem Soc 128:78
93. Yu J-Q, Giri R, Chen X (2006) Org Biomol Chem 4:4041
94. Daugulis O, Zaitsev VG (2005) Angew Chem Int Ed 44:4046
95. Daugulis O, Zaitsev V, Shabashov D, Pham Q-N, Lazareva A (2006) Synlett p 3382
96. Shabashov D, Daugulis O (2005) Org Lett 7:3657
97. Lazareva A, Daugulis O (2006) Org Lett 8:5211
98. Tobisu M, Chatani N (2006) Angew Chem Int Ed 45:1683
99. Dangel BD, Godula K, Youn SW, Sezen B, Sames D (2002) J Am Chem Soc 124:11856
100. Zaitsev VG, Shabashov D, Daugulis O (2005) J Am Chem Soc 127:13154
101. Reddy BVS, Reddy LR, Corey EJ (2006) Org Lett 8:3391
102. Lessene G, Feldman KS (2002) In: Astruc D (ed) Modern Arene Chemistry. Wiley, Weinheim, p 479
103. Li C-J, Li Z (2006) Pure Appl Chem 78:935
104. Waldvogel SR, Mirk D (2005) In: Dyker G (ed) Handbook of C-H Transformations. Wiley, Weinheim, p 251
105. Lee SH, Lee KH, Lee JS, Jung JD, Shim JS (1997) J Mol Catal A 115:241
106. Hull KL, Lanni EL, Sanford MS (2006) J Am Chem Soc 128:14047
107. Jia C, Kitamura T, Fujiwara Y (2001) Acc Chem Res 34:633
108. Boele MDK, van Strijdonck GPF, de Vries AHM, Kramer PCJ, De Vries JG, van Leeuwen PWNM (2002) J Am Chem Soc 124:1586
109. van Leeuwen PWNM, de Vries JG (2005) In: Dyker G (ed) Handbook of C-H Transformations. Wiley, Weinheim, p 203
110. Oi S, Fukita S, Inoue Y (1998) Chem Commun p 2439
111. Oi S, Sakai K, Inoue Y (2004) 51st Symposium on Organometallic Chemistry, Japan, Tokyo, Japan, Kinki Chemical Society, Japan: Osaka Abstract B202
112. Peterson AA, McNeill K (2006) Organometallics 25:4938
113. Ueura K, Miyamura S, Satoh T, Miura M (2006) J Organomet Chem 691:2821
114. Ueura K, Satoh T, Miura M (2005) Org Lett 7:2229
115. Kakiuchi F, Kan S, Igi K, Chatani N, Murai S (2003) J Am Chem Soc 125:1698
116. Kakiuchi F, Matsuura Y, Kan S, Chatani N (2005) J Am Chem Soc 127:5936
117. Bedford RB, Coles SJ, Hursthouse MB, Limmert ME (2003) Angew Chem Int Ed 42:112
118. Oi S, Watanabe S-I, Fukita S, Inoue Y (2003) Tetrahedron Lett 44:8665
119. Bedford RB, Limmert ME (2003) J Org Chem 68:8669
120. Kakiuchi F, Chatani N (2004) In: Murahashi S-I (ed) Ruthenium in Organic Synthesis. Wiley, Weinheim, p 219
121. Kakiuchi F, Chatani N (2004) In: Bruneau C, Dixneuf PH (eds) Ruthenium Catalysts and Fine Chemistry, vol 11. Springer, Berlin Heidelberg New York, p 45
122. Pastine SJ, Gribkov DV, Sames D (2006) J Am Chem Soc 128:14220
123. Park YJ, Jo E-A, Jun C-H (2005) Chem Commun p 1185
124. Oi S, Fukita S, Hirata N, Watanuki N, Miyano S, Inoue Y (2001) Org Lett 3:2579
125. Oi S, Ogino Y, Fukita S, Inoue Y (2002) Org Lett 4:1783
126. Oi S, Aizawa E, Ogino Y, Inoue Y (2005) J Org Chem 70:3113
127. Gant TG, Meyers AI (1994) Tetrahedron 50:2297
128. Oi S, Sakai K, Inoue Y (2005) Org Lett 7:4009
129. Littke AF, Fu GC (2002) Angew Chem Int Ed 41:4176
130. Bedford RB, Cazin CSJ (2002) Chem Commun p 2310
131. Hennessy E, Buchwald SL (2003) J Am Chem Soc 125:12084
132. Campeau L-C, Parisien M, Jean A, Fagnou K (2006) J Am Chem Soc 128:581
133. Ackermann L (2005) Org Lett 7:3123
134. Ackermann L, Althammer A, Born R (2006) Angew Chem Int Ed 45:2619
135. Percec V, Golding GM, Smidrkal J, Weichold O (2004) J Org Chem 69:3447
136. Tang Z-Y, Hu Q-S (2004) J Am Chem Soc 126:3058
137. Zhou J, Fu GC (2003) J Am Chem Soc 125:12527
138. Limmert ME, Roy AH, Hartwig JF (2005) J Org Chem 70:9364
139. Roy AH, Hartwig JF (2003) J Am Chem Soc 125:8704
140. Oi S, Tanaka Y, Inoue Y (2006) Organometallics 25:4773
141. Ko S, Kang B, Chang S (2005) Angew Chem Int Ed 44:455
142. Lee JM, Na Y, Han H, Chang S (2004) Chem Soc Rev 33:302