Catalysis by palladium complexes: New prospects in amination of aryl and hetaryl chlorides

Russian Chemical Reviews

Volumn 77, Issue 2, 2008, Pages 177-192

  Abaev, V T ^a   Serdyuk, O V ^b  

^a NORTH OSSETIAN STATE UNIVERSITY   (Russian Federation)

^b UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 43749107071     PISSN: 0036021X     EISSN: 14684837     Source Type: Journal    
DOI: 10.1070/RC2008v077n02ABEH003736     Document Type: Review

References (122)

1. J Tsuji Palladium Reagents and Catalysts: Innovation in Organic Synthesis (New York: Wiley, 1998)
2. J J Li, G W Gribble Palladium in Heterocyclic Chemistry. A Guide for the Synthetic Chemist (New York: Pergamon Press, 2000)
3. Handbook of Organopalladium Chemistry for Organic Synthesis. (Ed. E Negishi) (New York: Wiley, 2002)
4. A R Muci, S L Buchwald Top. Curr. Chem. 219 131 (2002)
5. B Schlummer, U Scholz Adv. Synth. Catal. 346 1599 (2004)
6. S L Buchwald, C Mauger, G Mignani, U Scholz Adv. Synth. Catal. 348 23 (2006)
7. F Paul, J Patt, J F Hartwig J. Am. Chem. Soc. 116 5969 (1994)
8. A S Guram, S L Buchwald J. Am. Chem. Soc. 116 7901 (1994)
9. J P Wolfe, S Wagaw, S L Buchwald J. Am. Chem. Soc. 118 7215 (1996)
10. M S Driver, J F Hartwig J. Am. Chem. Soc. 118 7217 (1996)
11. C G Frost, P Mendonca J. Chem. Soc., Perkin Trans. 1 2615 (1998)
12. J F Hartwig Angew. Chem., Int. Ed. 37 2046 (1998)
13. V V Grashin, H Alper Chem. Rev. 94 1047 (1994)
14. A F Littke, G C Fu Angew. Chem., Int. Ed. 41 4176 (2002)
15. J-P Corbet, G Mignani Chem. Rev. 106 2651 (2006)
16. C J Smith, M W S Tsang, A B Holmes, R L Danheiser, J W Tester Org. Biomol. Chem. 3 3767 (2005)
17. G V Salmoria, E Dall'Oglio, C Zucco Tetrahedron Lett. 39 2471 (1998)
18. G Luo, L Chen, G S Poindexter Tetrahedron Lett. 43 5739 (2002)
19. Y-J Cherng Tetrahedron 58 1125 (2002)
20. B U W Maes, K T J Loones, G L F Lemière, R A Dommisse Synlett 1822 (2003)
21. G Burton, P Cao, G Li, R Rivero Org. Lett. 5 4373 (2003)
22. T A Jensen, X Liang, D Tanner, N Skjaerbaek J. Org. Chem. 69 4936 (2004)
23. B U W Maes, K T J Loones, S Hostyn, G Diels, G Rombouts Tetrahedron 60 11559 (2004)
24. U Christmann, R Vilar Angew. Chem., Int. Ed. 44 366 (2005)
25. J F Hartwig Synlett 329 (1997)
26. M W Hooper, M Utsinomiya, J F Hartwig J. Org. Chem. 68 2861 (2003)
27. S Shekhar, P Ryberg, J F Hartwig, J S Mathew, D G Blackmond, E R Strieter, S L Buchwald J. Am. Chem. Soc. 128 3584 (2006)
28. L M Klingensmith, E R Strieter, T E Barder, S L Buchwald Organometallics 25 82 (2006)
29. J F Hartwig, F Paul J. Am. Chem. Soc. 117 5373 (1995)
30. B C Hamann, J F Hartwig J. Am. Chem. Soc. 120 3694 (1998)
31. E R Strieter, D G Blackmond, S L Buchwald J. Am. Chem. Soc. 125 13978 (2003)
32. T E Barder, M R Biscoe, S L Buchwald Organometallics 26 2183 (2007)
33. F Barrios-Landeros, J F Hartwig J. Am. Chem. Soc. 127 6944 (2005)
34. L M Alcazar-Roman, J F Hartwig J. Am. Chem. Soc. 123 12905 (2001)
35. J Louie, J F Hartwig Tetrahedron Lett. 36 3609 (1995)
36. M S Driver, J F Hartwig J. Am. Chem. Soc. 117 4708 (1995)
37. J F Hartwig, S Richards, D Barañano, F Paul J. Am. Chem. Soc. 118 3626 (1996)
38. M S Driver, J F Hartwig J. Am. Chem. Soc. 119 8232 (1997)
39. J F Hartwig Acc. Chem. Res. 31 852 (1998)
40. A H Roy, J F Hartwig J. Am. Chem. Soc. 123 1232 (2001)
41. M Yamashita, J F Hartwig J. Am. Chem. Soc. 126 5344 (2004)
42. K Fujita, M Yamashita, F Puschmann, M M Alvarez-Falcon, C D Incarvito, J F Hartwig J. Am. Chem. Soc. 128 9044 (2006)
43. J F Hartwig Inorg. Chem. 46 1936 (2007)
44. P W N M van Leeuwen, P C J Kamer, J N H Reek, P Dierkes Chem. Rev. 100 2741 (2000)
45. P C J Kamer, P W N M van Leeuwen, J N H Reek Acc. Chem. Res. 34 895 (2001)
46. N Cabello-Sanchez, L Jean, J Maddaluno, M-C Lasne, J Rounden J. Org. Chem. 72 2030 (2007)
47. C Meyers, B U W Maes, K T J Loones, G Bal, G L F Lemière, R A Dommisse J. Org. Chem. 69 6010 (2004)
48. N P Reddy, M Tanaka Tetrahedron Lett. 38 4807 (1997)
49. M Nishiyama, T Yamamoto, Y Koie Tetrahedron Lett. 39 617 (1998)
50. T Yamamoto, M Nishiyama, Y Koie Tetrahedron Lett. 39 2367 (1998)
51. A C Frisch, A Zapf, O Briel, B Kayser, N Shaikh, M Beller J. Mol. Catal. A: Chem. 214 231 (2004)
52. S Lee, M Jørgensen, J F Hartwig Org. Lett. 3 2729 (2001)
53. J F Hartwig, M Kawatsura, S I Hauck, K H Shaughnessy, L M Alcazar-Roman J. Org. Chem. 64 5575 (1999)
54. M Watanabe, M Nishiyama, T Yamamoto, Y Koie Tetrahedron Lett. 41 481 (2000)
55. R Kuwano, M Utsunomiya, J F Hartwig J. Org. Chem. 67 6479 (2002)
56. A Ehrentraut, A Zapf, M Beller J. Mol. Catal. A: Chem. 182-183 515 (2002)
57. X Bei, A S Guram, H W Turner, W H Weinberg Tetrahedron Lett. 40 1237 (1999)
58. X Bei, T Uno, J Norris, H W Turner, W H Weinberg, A S Guram Organometallics 18 1840 (1999)
59. C C Mauger, G A Mignani Aldrichim. Acta 39 17 (2006)
60. K W Anderson, R E Tundel, T Ikawa, R A Altman, S L Buchwald Angew. Chem., Int. Ed. 45 6523 (2006)
61. D W Old, J P Wolfe, S L Buchwald J. Am. Chem. Soc. 120 9722 (1998)
62. S D Edmondson, A Mastracchio, E R Parmee Org. Lett. 2 1109 (2000)
63. J P Wolfe, H Tomori, J P Sadighi, J Yin, S L Buchwald J. Org. Chem. 65 1158 (2000)
64. M C Harris, X Huang, S L Buchwald Org. Lett. 4 2885 (2002)
65. X Huang, S L Buchwald Org. Lett. 3 3417 (2001)
66. X Huang, K W Anderson, D Zim, L Jiang, A Klapars, S L Buchwald J. Am. Chem. Soc. 125 6653 (2003)
67. M C Harris, S L Buchwald J. Org. Chem. 65 5327 (2000)
68. D W Old, M C Harris, S L Buchwald Org. Lett. 2 1403 (2000)
69. R A Singer, S Caron, R E McDermott, P Arpin, N M Do Synthesis (Spec. Iss.) 1727 (2003)
70. X Xie, T Y Zhang, Z Zhang J. Org. Chem. 71 6522 (2006)
71. F Rataboul, A Zapf, R Jackstell, S Harkal, T Riermeier, A Monsees, U Dingerdissen, M Beller Chem. - Eur. J. 10 2983 (2004)
72. N Kataoka, Q Shelby, J P Stambuli, J F Hartwig J. Org. Chem. 67 5553 (2002)
73. G Zeni, R C Larock Chem. Rev. 106 4644 (2006)
74. M Watanabe, T Yamamoto, M Nishiyama Angew. Chem., Int. Ed. 39 2501 (2000)
75. C A Fleckenstein, H Plenio Chem. - Eur. J. 13 2701 (2007)
76. C A Fleckenstein, H Plenio Organometallics 26 2758 (2007)
77. S Urgaonkar, M Nagarajan, J G Verkade J. Org. Chem. 68 452 (2003)
78. S Urgaonkar, J G Verkade J. Org. Chem. 69 9135 (2004)
79. S Urgaonkar, M Nagarajan, J G Verkade Tetrahedron Lett. 43 8921 (2002)
80. J You, J G Verkade Angew. Chem., Int. Ed. 42 5051 (2003)
81. B C Hamann, J F Hartwig J. Am. Chem. Soc. 120 7369 (1998)
82. Q Shen, J F Hartwig J. Am. Chem. Soc. 128 10028 (2006)
83. S Jaime-Figueroa, Y Liu, J M Muchowski, D G Putman Tetrahedron Lett. 39 1313 (1998)
84. J B Atreburn, K Venkateswara Rao, R Ramdas, B R Dible Org. Lett. 3 1351 (2001)
85. X-L Wang, X-F Zheng, J Reiner Synlett 942 (2006)
86. S Wagaw, S L Buchwald J. Org. Chem. 61 7240 (1996)
87. Y Hong, G J Tanoury, H S Wilkinson, R P Bakale, S A Wald, C H Senanayake Tetrahedron Lett. 38 5607 (1997)
88. Y Hong, C H Senanayake, T Xiang, C P Vandenbossche, G J Tanoury, R P Bakale, S A Wald Tetrahedron Lett. 39 3121 (1998)
89. N Chida, T Suzuki, S Tanaka, I Yamada Tetrahedron Lett. 40 2573 (1999)
90. J Rouden, A Bernard, M-C Lasne Tetrahedron Lett. 40 8109 (1999)
91. J Košmrlj, B U W Maes, G L F Lemière, A Haemers Synlett 1581 (2000)
92. T H Jonckers, B U W Maes, G L F Lemière, G Rombouts, L Pieters, A Haemers, R A Dommisse Synlett 615 (2003)
93. T H M Jonckers, B U W Maes, G L F Lemière, R Dommisse Tetrahedron 57 7027 (2001)
94. L F Frey, K Marcantonio, D E Frantz, J A Murry, R D Tillyer, E J J Grabowski, P J Reider Tetrahedron Lett. 42 6815 (2001)
95. I P Beletskaya, A D Averin, A G Bessmertnykh, R Guilard Tetrahedron Lett. 42 4987 (2001)
96. I P Beletskaya, A D Averin, A G Bessmertnykh, R Guilard Tetrahedron Lett. 42 4983 (2001)
97. I P Beletskaya, A D Averin, A G Bessmertnykh, F Denat, R Guilard Tetrahedron Lett. 43 1193 (2002)
98. J Yin, M M Zhao, M A Huffman, J M McNamara Org. Lett. 4 3481 (2002)
99. J Dupont, M Pfeffer, J Spencer Eur. J. Inorg. Chem. 1917 (2001)
100. J Dupont, C S Consorti, J Spencer Chem. Rev. 105 2527 (2005)
101. W A Herrmann, K Öfele, D V Preysing, S K Schneider J. Organomet. Chem. 687 229 (2003)
102. M Beller, T H Riermeier, C-P Reisinger, W A Herrmann Tetrahedron Lett. 38 2073 (1997)
103. T H Riermeier, A Zapf, M Beller Top. Catal. 4 301 (1997)
104. J Louie, J F Hartwig Angew. Chem., Int. Ed. 35 2359 (1996)
105. M Beller, C Breindl, T H Riermeier, A Tillack J. Org. Chem. 66 1403 (2001)
106. D Zim, S L Buchwald Org. Lett. 5 2413 (2003)
107. R B Bedford, C S J Cazin, S J Coles, T Gelbrich, P N Norton, M B Hursthouse, M E Light Organometallics 22 987 (2003)
108. R B Bedford, M E Blake Adv. Synth. Catal. 345 1107 (2003)
109. M S Viciu, R A Kelly III, E D Stevens, F Naud, M Studer, S P Nolan Org. Lett. 5 1479 (2003)
110. A Schnyder, A F Indolese, M Studer, H-U Blaser Angew. Chem., Int. Ed. 41 3668 (2002)
111. C Xu, J-F Gong, Y-J Wu Tetrahedron Lett. 48 1619 (2007)
112. G Y Li, G Zheng, A F Noonan J. Org. Chem. 66 8677 (2001)
113. G Y Li Angew. Chem., Int. Ed. 40 1513 (2001)
114. E A B Kantchev, C J O'Brien, M G Organ Aldrichim. Acta 39 97 (2006)
115. J C Green, B J Herbert, R Lonsdale J. Organomet. Chem. 690 6054 (2005)
116. J Huang, G Grasa, S P Nolan Org. Lett. 1 1307 (1999)
117. G A Grasa, M S Viciu, J Huang, S P Nolan J. Org. Chem. 66 7729 (2001)
118. S R Stauffer, S Lee, J P Stambuli, S I Hauck, J F Hartwig Org. Lett. 2 1423 (2000)
119. M S Viciu, R M Kissling, E D Stevens, S P Nolan Org. Lett. 4 2229 (2002)
120. J Cheng, M L Trudell Org. Lett. 3 1371 (2001)
121. S Ding, N S Gray, X Wu, Q Ding, P G Schultz J. Am. Chem. Soc. 124 1594 (2002)
122. E Teuma, C Lyon-Saunier, H Gornitzka, G Mignani, A Baceiredo, G Bertrand J. Organomet. Chem. 690 5541 (2005)