Palladium-Catalyzed Arylations of Amines and α-C-H Acidic Compounds

Modern Arylation Methods

Volumn , Issue , 2009, Pages 69-120

  Schlummer, Björn ^a   Scholz, Ulrich ^b  

^a Saltigo GmbH   (Germany)

^b BOEHRINGER INGELHEIM PHARMA GMBH AND CO KG   (Germany)

Author keywords

Alpha arylation; Amines; Buchwald Hartwig amination; Cross coupling; Palladium catalysis; Phosphines

Indexed keywords

EID: 84891021758     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527627325.ch3     Document Type: Chapter

References (325)

1. de Meijere, A. and Diederich, F. (eds) (2004) Metal-Catalyzed Cross Coupling Reactions, Wiley-VCH Verlag GmbH, Weinheim;
2. Nicolaou, K.C., Bulger, P.G. and Sarlah, D. (2005) Angew. Chem. Int. Ed., 44, 4442-89;
3. Negishi, E.i. (ed.) (2002) Handbook of Organopalladium Chemistry for Organic Synthesis, John Wiley & Sons, Inc., Hoboken, N.J.
4. King, A.O. and Yasuda, N. (2004) Top. Organomet. Chem., 6, 205-45.
5. Guram, S., Rennels, R.A., Buchwald, S.L., Barta, N.S. and Pearson, W.H. (1996) Chemtracts Inorg. Chem., 8, 1-5;
6. Hartwig, J.F. (1997) Synlett, 329-40;
7. Wolfe, J.P., Wagaw, S., Marcoux, J.F. and Buchwald, S.L. (1998) Acc. Chem. Res., 31, 805-18;
8. Hartwig, J.F. (1998) Acc. Chem. Res., 31, 852-60 ;
9. Hartwig, J.F. (1998) Angew. Chem. Int. Ed., 37, 2046-2067;
10. Yang, B.H. and Buchwald, S.L. (1999) J. Organomet. Chem., 576, 125-46;
11. Mud, A.R. and Buchwald, S.L. (2002) Top. Curr. Chem., 219, 131-209;
12. Hartwigin, J.F. (2002) Modern Arene Chemistry (ed. D. Astruc), Wiley-VCH Verlag GmbH, Weinheim, pp. 107-68;
13. Prim, D., Campagne, J.M., Joseph, D. and Andrioletti, B. (2002) Tetrahedron, 58, 2041-75;
14. Littke, A.F. and Fu, G.C. (2002) Angew. Chem. Int. Ed., 41, 4176-211;
15. Hartwig, J.F. (2004) Comprehensive Coordination Chemistry II, 9, 369-98;
16. Hartwig, J.F. (2006) Synlett, 9, 1283-94.
17. Schlummer, B. and Scholz, U. (2004) Adv. Synth. Catal., 346, 1599-626.
18. Culkin, D.A. and Hartwig, J.F. (2003) Acc. Chem. Res., 36, 234-45;
19. Lloyd-Jones, G.C. (2002) Angew. Chem. Int. Ed., 41, 953-6.
20. Crampton, M.R. (1977) Nucleophilic aromatic substitution, in Organic Reaction Mechanisms, Vol. 12, John Wiley & Sons, Ltd, pp. 279-97;
21. Vlasov, V.M. (2003) Russ. Chem. Rev., 72, 681-703.
22. Turpin, G.S. (1891) J. Chem. Soc., 714 ;
23. Abegg, R. (1891) Ber. d. Chem. Ges., 24, 949-58;
24. Pisani, F. (1854) Compt. Rend., 39, 852.
25. Kym, O. (1895) J. Prakt. Chem., 325-36.
26. Laubenheimer, A. (1876) Chem. Ber., 9, 1826-9 ;
27. Laubenheimer, A. (1878) Chem. Ber., 11, 1155-61 ;
28. Rudy, H. and Cramer, K.E. (1939) Chem. Ber., 72B, 227-48.
29. Bergstrom, F.W., Granara, I.M. and Erickson, V. (1942) J. Org. Chem., 98-102 ;
30. Stern, M.K. and Cheng, B.K. (1993) J. Org. Chem., 58, 6883-8;
31. Stern, M.K. (1992) US A 5117063, 19920526;
32. De Vera, A.L. (2001) WO A2 2001098252, 20011227.
33. Stella, L., Raynier, B. and Surzur, J.M. (1981) Tetrahedron, 37, 2843-54 ;
34. Minisci, F. (1976) Top. Curr. Chem., 62, 1-48;
35. Minisci, F., Galli, R., Cecere, M. and Quilico, A. (1969) FR 93635, 19690425;
36. Minisci, F., Galli, R. and Cecere, M. (1966) Chem. Ind., 48, 1324-6.
37. Ullmann, F. and Bielecki, J. (1901) Chem. Ber., 34, 2174-85.
38. Ullmann, F. (1903) Chem. Ber., 36, 2382-4.
39. Goldberg, I. and Ullmann, D.E. (1905) 173523.
40. Kunz, K., Scholz, U. and Ganzer, D. (2003) Synlett, 2428-39 ;
41. Beletskaya, I.P. and Cheprakov, A.V. (2004) Coord. Chem. Rev., 248, 2337-64;
42. Nelson, T.D. and Crouch, D.R. (2004) Org. React., 63, 265-555.
43. Heck, R.F. (2006) Synlett, 2855-60.
44. Miyaura, N., Yanagi, T. and Suzuki, A. (1981) Synth. Commun., 11, 513-19.
45. Milstein, D. and Stille, J.K. (1979) J. Am. Chem. Soc., 101, 4992-8.
46. Negishi, E.-i., Zeng, X., Tan, Z., Qian, M., Hu, Q. and Huangin, Z. (2004) Metal-Catalyzed Cross-Coupling Reactions, 2nd edn (eds A. De Meijere and F. Diederich), Wiley-VCH Verlag GmbH, Weinheim, pp. 815-89.
47. Kosugi, M., Kameyama, M.M. and Migita, T. (1983) Chem. Lett., 12, 927-8.
48. Singh, A.K. and Bhandari, S. (2003) Main Group Metal. Chem., 26, 155-211.
49. Boger, D.L., Duff, S.R., Panek, J.S. and Yasuda, M. (1985) J. Org. Chem., 50, 5782-9.
50. Dzhemilev, U.M., Ibragimov, A.G., Minsker, D.L. and Muslukhov, R.R. (1987) Izvestiya Akad. Nauk SSSR, Seriya Khim., 2, 406-9.
51. Guram, A.S. and Buchwald, S.L. (1994) J. Am. Chem. Soc., 116, 7901-2.
52. Buchwald, S.L. (1996), US A 5576460, 19961119;
53. Guram, A.S., Rennels, R.A. and Buchwald, S.L. (1995) Angew. Chem. Int. Ed., 34, 1348-50.
54. Louie, J. and Hartwig, J.F. (1995) Tetrahedron Lett., 36, 3609-12.
55. Monguchi, Y., Kitamoto, K., Mori, S., Yanase, T., Mizoguchi, Y., Ikawa, T., Maegawa, T. and Sajiki, H. (2007) Abstracts of Papers. 233rd ACS National Meeting, March 25-29, Chicago, IL, United States.
56. Matthews, M.A. (2005) Green chemistry, in Kirk-Othmer Encyclopedia of Chemical Technology, Vol. 12, 5th edn (ed. A. Seidel), John Wiley & Sons, Inc., Hoboken, NJ, pp. 799-818.
57. Fairlamb, I.J.S., Kapdi, A.R., Lee, A.F., McGlacken, G.P., Weissburger, F., de Vries, A.H.M. and Schmieder-van de Vondervoort, L. (2006) Chem. Eur.J., 12, 8750-61.
58. Kozlov, N.S., Pinegina, L. and Tselishchev, B.E. (1968) Zh. Khim., Abstr. No. 9, h230.
59. Huang, X., Anderson, K.W., Zim, D., Jiang, L., Klapars, A. and Buchwald, S.L. (2003) J. Am. Chem. Soc., 125, 6653-5 ;
60. Strieter, E.R., Blackmond, D.G. and Buchwald, S.L. (2003) J. Am. Chem. Soc., 125, 13978-80.
61. Buchwald, S.L. and Anderson, K.W. (2006) WO 2006074315.
62. Herrmann, W.A., Xfele, K., Preysing, D.v. and Schneider, S.K. (2003) J. Organomet. Chem., 687, 229-48.
63. Nishio, R., Wessely, S., Sugiura, M. and Kobayashi, S. (2006) J. Comb. Chem., 8, 459-61.
64. Nettekoven, U., Naud, F., Schnyder, A. and Blaser, H.-U. (2004) Synlett, 2549-52.
65. Guino, M. and (Mimi) Hii, K.K. (2005) Tetrahedron Lett., 46, 6911-13;
66. Rosso, V.W., Lust, D.A., Bernot, P.J., Grosso, J.A., Modi, S.P., Rusowicz, A., Sedergran, T.C., Simpson, J.H., Srivastava, S.K., Humora, M.J. and Anderson, N.G. (1997) Org. Proc. Res. Dev., 1, 311-14;
67. Garrett, C.E. and Prasad, K. (2004) Adv. Synth. Catal., 346, 889-900.
68. For an interesting overview of monoligated palladium species as catalysts in cross-coupling, see: Christmann, U. and Vilar, R. (2005) Angew. Chem. Int. Ed., 44, 366-74.
69. For a comparison of phosphine-and carbene-based ligands, see: Frisch, C., Beller, A., Zapf, A., Briel, O., Kayser, B., Shaikh, N. and Beller, M. (2004) J. Mol. Catal. A, 214, 231-9.
70. Wolfe, J.P., Wagaw, S. and Buchwald, S.L. (1996) J. Am. Chem. Soc., 118, 7215-16;
71. Alcazar-Roman, L.M., Hartwig, J.F., Rheingold, A.L., Liable-Sands, L.M. and Guzei, I.A. (2000) J. Am. Chem. Soc., 122, 4618-30 ;
72. Singh, U.K., Strieter, E.R., Blackmond, D.G. and Buchwald, S.L. (2002) J. Am. Chem. Soc., 124, 14104-14.
73. Shekhar, S., Ryberg, P., Hartwig, J.F., Mathew, J.S., Blackmond, D.G., Strieter, E.R. and Buchwald, S.L. (2006) J. Am. Chem. Soc., 128, 3584-91.
74. Prashad, M., Hu, B., Lu, Y.M., Draper, R., Har, D., Repic, O. and Blacklock, T.J. (2000) J. Org. Chem., 68, 2612-14.
75. Laufer, R.S. and Dmitrienko, G.I. (2002) J. Am. Chem. Soc., 124, 1854-5.
76. Wolfe, J.P. and Buchwald, S.L. (2000) J. Org. Chem., 65, 1144-57.
77. Wolfe, J.P. and Buchwald, S.L. (1997) J. Org. Chem., 62, 6066-8.
78. Marinetti, A., Hubert, P. and Genêt, J.P. (2000) Eur.J. Org. Chem., 1815-20;
79. Wagaw, S., Rennels, R.A. and Buchwald, S.L. (1997) J. Am. Chem. Soc., 119, 8451-8.
80. Wolfe, J.P. and Buchwald, S.L. (1997) J. Org. Chem., 62, 1264-7;
81. Ahman, J. and Buchwald, S.L. (1997) Tetrahedron Lett., 38, 6363-6;
82. Demadrille, R., Moustrou, C., Samat, A. and Guglielmetti, R. (1999) Heterocyclic Commun., 5, 123 ;
83. Wentland, M.P., Xu, G., Cioffi, C.L., Ye, Y., Duan, W., Cohen, D.J., Colasurdo, A.M. and Bidlack, J.M. (2000) Bioorg. Med. Chem. Lett., 10, 183-7.
84. Hong, Y., Senanayake, C.H., Xiang, T., Vandenbossche, C.P., Tanoury, G.J., Bakale, R.P. and Wald, S.A. (1998) Tetrahedron Lett., 39, 3121-4.
85. Kanbara, T., Izumi, K., Nakadani, Y., Narise, T. and Hasegawa, K. (1997) Chem. Lett., 26, 1185-6.
86. Zhang, X.X., Harris, M.C., Sadighi, J.P. and Buchwald, S.L. (2001) Can.J. Chem., 79, 1799-805.
87. Ferreira, I.C.F.R., Queiroz, M.J.R.P. and Kirsch, G. (2003) Tetrahedron, 59, 975-81.
88. Guari, Y., van Strijdonck, G.P.F., Boele, M.D.K., Reek, J.N.H., Kramer, P.C.J. and van Leeuwen, P.W.N.M. (2001) Chem. Eur. J., 7, 475-82.
89. Yin, J. and Buchwald, S.L. (2002) J. Am. Chem. Soc., 124, 6043-8.
90. Yin, J. and Buchwald, S.L. (2000) Org. Lett., 2, 1101-4;
91. Yang, B.H. and Buchwald, S.L. (1999) Org. Lett., 1, 35-7.
92. Wagaw, S., Yang, B.H. and Buchwald, S.L. (1999) J. Am. Chem. Soc., 121, 10251-63.
93. Cacchi, S., Fabrizi, G., Goggiamani, A. and Zappia, G. (2001) Org. Lett., 3, 2539-41.
94. Artamkina, G.A., Sergeev, A.G. and Beletskaya, I.P. (2001) Tetrahedron Lett., 42, 4381-4.
95. Harris, M.C., Geis, O. and Buchwald, S.L. (1999) J. Org. Chem., 64, 6019-22.
96. Yin, J., Zhao, M.M., Huffman, M.A. and McNamara, J.M. (2002) Org. Lett., 4, 3481-4.
97. For recent applications, see: Wang, W., Ding, Q., Fan, R. and Wu, J. (2007) Tetrahedron Lett., 48, 3647-9;
98. Begouin, A., Hesse, S., Queiroz, M.-J.R.P. and Kirsch, G. (2007) Eur.J. Org. Chem., 10, 1678-82;
99. Hostyn, S., Maes, B.U.W., Van Baelen, G., Gulevskaya, A., Meyers, C. and Smits, K. (2006) Tetrahedron, 62, 4676-84.
100. Sadighi, J.P., Harris, M.C. and Buchwald, S.L. (1998) Tetrahedron Lett., 39, 5327-30.
101. Ogasawara, M., Yoshehida, K. and Hayashi, T. (2000) Organometallics, 19, 1567-71.
102. Old, D.W., Wolfe, J.P. and Buchwald, S.L. (1998) J. Am. Chem. Soc., 120, 9722-3.
103. Wolfe, J.P., Tomori, H., Sadighi, J.P., Yin, J. and Buchwald, S.L. (2000) J. Org. Chem., 65, 1158-74.
104. Old, D.W., Wolfe, J.P. and Buchwald, S.L. (1998) J. Am. Chem. Soc., 120, 9722-3.
105. Zhang, X.X. and Buchwald, S.L. (2000) J. Org. Chem., 65, 8027-31.
106. Tomori, H., Fox, J.M. and Buchwald, S.L. (2000) J. Org. Chem., 65, 5334;
107. Buchwald, S.L., Mauger, C., Mignani, G. and Scholz, U. (2006) Adv. Synth. Catal., 348, 23-39.
108. Damon, D.B., Dugger, R.W., Magnus-Aryitey, G., Ruggeri, R.B., Wester, R.T., Tu, M. and Abramov, Y. (2006) Org. Proc. Res. Dev., 10, 464-71.
109. Wolfe, J.P. and Buchwald, S.L. (1999) Angew. Chem. Int. Ed., 38, 2413-16.
110. Xu, C., Gong, J.-F. and Wu, Y.-J. (2007) Tetrahedron Lett., 48, 1619-23.
111. Barder, T.E. and Buchwald, S.L. (2007) J. Am. Chem. Soc., 129, 5096-101.
112. Schlummer, B. and Scholz, U. (2005) Spec. Chem. Mag., 25, 22-4;
113. Schlummer, B. and Scholz, U. (2005) Chim. Oggi, 23, 18-20.
114. Nishiyama, M. and Koie, Y. (1997), EP A1 802173;
115. Yamamoto, T., Nishiyama, S. and Koie, Y. (1998) JP A2 10310561, 19981124;
116. Yamamoto, T., Nishiyama, S. and Koie, Y. (1999) JP A2 11080346, 19990326.
117. FMC Lithium (2008) http://www.fmclithium.com/index.html (accessed 12 September 2008);
118. STREM (2008) http://www.strem.com/code/index.ghc (accessed 12 September 2008).
119. Netherton, M.R. and Fu, G.C. (2001) Org. Lett., 3, 4295-8.
120. Nishiyama, M., Yamamoto, T. and Koie, Y. (1998) Tetrahedron Lett., 39, 617-20.
121. Hartwig, J.F., Kawatsura, M., Hauck, S.I., Shaughnessy, K.H. and Alcazar-Roman, L.M. (1999) J. Org. Chem., 64, 5575-80.
122. Louie, J., Hartwig, J.F. and Fry, A.J. (1997) J. Am. Chem. Soc., 119, 11695-6;
123. Louie, J. and Hartwig, J.F. (1998) Macromolecules, 31, 6737-93 ;
124. Goodson, F.E. and Hartwig, J.F. (1998) Macromolecules, 31, 1700-3;
125. Yamamoto, T., Nishiyama, M. and Koie, Y. (1998) Tetrahedron Lett., 39, 2367-70 ;
126. Goodson, F.E., Hauck, S.I. and Hartwig, J.F. (1999) J. Am. Chem. Soc., 121, 7527-39.
127. Reddy, N.P. and Tanaka, M. (1997) Tetrahedron Lett., 38, 4807-10.
128. Hauck, S. I., Lakshmi, K.V. and Hartwig, J.F. (1999) Org. Lett., 1, 2057-60;
129. Tew, G.N., Pralle, M.U. and Stupp, S.I. (2000) Angew. Chem. Int. Ed., 39, 517-21 ;
130. Braig, T., Müller, D.C., Groβ, M., Meerholz, K. and Nuyken, O. (2000) Macromol. Rapid Commun. 21, 583-9;
131. Thelakkhat, M., Hagen, J., Haarer, D. and Schmidt, H.W. (1999) Synthetic Methods, 102, 1125-8.
132. Wolfe, J.P. and Buchwald, S.L. (1996) J. Org. Chem., 61, 1133-5;
133. Zhao, S.H., Miller, A.K., Berger, J. and Flippin, L.A. (1996) Tetrahedron Lett., 37, 4463-6.
134. Kocovsky, P. (2003) J. Organomet. Chem., 687, 256-68;
135. Vysko il, S., Smrcina, M. and Kocovsky, P. (1998) Tetrahedron Lett., 39, 9289-92.
136. Driver, M.S. and Hartwig, J.F. (1996) J. Am. Chem. Soc., 118, 7217-18.
137. Louie, J., Driver, M.S., Hamann, B.C. and Hartwig, J.F. (1997) J. Org. Chem., 62, 1268-73.
138. Beletskaya, I.P., Bessmertnykh, A.G. and Guilard, R. (1999) Synlett, 1459-61.
139. Marcoux, J.-F., Wagaw S. and Buchwald, S.L. (1997) J. Org. Chem., 62, 1568-9.
140. Wolfe, J.P. and Buchwald, S.L. (1997) Tetrahedron Lett., 38, 6359-62.
141. Shen, Q., Shekhar, S., Stambuli, J.P. and Hartwig, J.F. (2005) Angew. Chem. Int. Ed., 44, 1371-5.
142. Watanabe, M., Yamamoto, T. and Nishiyama, M. (2000), EP A2 1035114, 20000913;
143. Watanabe, M., Yamamoto, T. and Nishiyama, M. (2000) Angew. Chem. Int. Ed., 39(14), 2501-4.
144. Kataoka, N., Shelby, Q., Stambuli, J.P. and Hartwig, J.F. (2002) J. Org. Chem., 67, 5553-66.
145. Hamann, B.C. and Hartwig, J.F. (1998) J. Am. Chem. Soc., 120, 7369-70.
146. Kantchev, E.A.B., O'Brien, C.J. and Organ, M.G. (2007) Angew. Chem. Int. Ed., 46, 2768-813;
147. Tekavec, T.N. and Louie, J. (2007) Top. Organomet. Chem., 21, 159-92;
148. Diez-Gonzalez, S. and Nolan, S.P. (2007) Top. Organomet. Chem., 21, 47-82 ;
149. Glorius, F. (2007) Top. Organomet. Chem., 21, 1-20;
150. Herrmann, W.A. (2002) Angew. Chem. Int. Ed., 41(8), 1290-309.
151. Harries-Rees, K., Chauvin, Y., Grubbs, R. and Schrock, R. (2005) Chem. World, 2, 42-4.
152. Krafczyk, A.J., III, Arduengo, R. and Schmuter, R. (1999) Tetrahedron, 55, 14523-34.
153. Fuerstner, A., Alcarazo, M., Cesar, V. and Lehmann, C.W. (2006) Chem. Commun., 2176-8.
154. Caddick, S., Cloke, F.G.N., Clentsmith, G.K.B., Hitchcock, P.B., McKerrecher, D., Titcomb, L.R. and Williams, M.R.V.J. (2001) J. Organomet. Chem., 617, 635-9.
155. Stauffer, S.R., Lee, S., Stambuli, J.P., Hauck, S.I. and Hartwig, J.F. (2000) Org. Lett., 2, 1423-6.
156. Lerma, I.C., Cawley, M.J., Cloke, F.G.N., Arentsen, K., Scott, J.S., Pearson, S.E., Hayler, J. and Caddick, S. (2005) J. Organomet. Chem., 690, 5841-8.
157. Omar-Amrani, R., Schneider, R. and Fort, Y. (2004) Synthesis, 2527-34.
158. Urgaonkar, S., Xu, J.H. and Verkade, J.G. (2003) J. Org. Chem., 68, 8416-23.
159. Urgaonkar, S., Nagarajan, M. and Verkade, J.G. (2003) Org. Lett., 5, 815-18;
160. Urgaonkar, S. and Verkade, J.G. (2004) J. Org. Chem., 69, 9135-42;
161. Urgaonkar, S., Xu, J.-H. and Verkade, J.G. (2004) J. Org. Chem., 69(26), 9323.
162. Nandakumar, M.V. and Verkade, J.G. (2005) Tetrahedron, 61, 9775-82.
163. Urgaonkar, S. and Verkade, J.G. (2004) Adv. Synth. Catal., 346, 611-16.
164. Singer, R.A., Caron, S., McDermott, R.E., Arpin, P. and Do, N.M. (2003) Synthesis, 1727-31.
165. Singer, R.A., Dore, M., Sieser, J.E. and Berliner, M.A. (2006) Tetrahedron Lett., 47, 3727-31.
166. Singer, R.A., Tom, N.J., Frost, H.N. and Simon, W.M. (2004) Tetrahedron Lett., 45, 4715-18.
167. Beller, M., Ehrentraut, A., Fuhrmann, C. and Zapf, A. (2002) WO A1 2002010178, 20020207;
168. Ehrentraut, A., Zapf, A. and Beller, M. (2002) J. Mol. Catal. A, 182-3, 515-523;
169. Harkal, S., Rataboul, F., Zapf, A., Fuhrmann, C., Riermeier, T., Monsees, A. and Beller, M. (2004) Adv. Synth. Catal., 346, 1742-8 ;
170. Rataboul, F., Zapf, A., Jackstell, R., Harkal, S., Riermeier, T., Monsees, A., Dingerdissen, U. and Beller, M. (2004) Chem. Eur. J., 10, 2983-90.
171. Bei, X.H., Uno, T., Norris, J., Turner, H.W., Weinberg, W.H., Guram, A.S. and Peterson, J.L. (1999) Organometallics, 18, 1840-53.
172. Li, G.Y., Zheng, G. and Noonan, A.F. (2001) J. Org. Chem., 66, 8677-81.
173. Ackermann, L. and Born, R. (2005) Angew. Chem. Int. Ed., 44, 2444-7.
174. Ackermann, L. (2007) Synlett, 4, 507-26.
175. Ackermann, L., Born, R., Spatz, J.H., Althammer, A. and Gschrei, C.J. (2006) Pure Appl. Chem., 78, 209-14.
176. Liu, D., Gao, W., Dai, Q. and Zhang, X. (2005) Org. Lett., 7, 4907-10.
177. Xie, X., Zhang, T.Y. and Zhang, Z. (2006) J. Org. Chem., 71, 6522-9.
178. Hill, L.L., Moore, L.R., Huang, R., Craciun, R., Vincent, A.J., Dixon, D.A., Chou, J., Woltermann, C.J. and Shaughnessy, K.H. (2006) J. Org. Chem., 71, 5117-25.
179. Lee, J.-C., Wang, M.-G. and Hong, F.-E. (2005) Eur.J. Inorg. Chem., 24, 5011-17.
180. Brenstrum, T., Clattenburg, J., Britten, J., Zavorine, S., Dyck, J., Robertson, A.J., McNulty, J. and Capretta, A. (2006) Org. Lett., 8, 103-5.
181. Gerristma, D., Brenstrum, T., McNulty, J. and Capretta, A. (2004) Tetrahedron Lett., 45, 8319-21.
182. Teuma, E., Lyon-Saunier, C., Gornitzka, H., Mignani, G., Baceiredo, A. and Bertrand, G. (2005) J. Organomet. Chem., 690, 5541-5.
183. Meyers, C., Maes, B.U.W., Loones, K.T.J., Bal, G., Lemiere, G.L.F. and Dommisse, R.A. (2004) J. Org. Chem., 69, 6010-17 ;
184. Shaughnessy, K.H. and Booth, R.S. (2001) Org. Lett., 3, 2757 ;
185. DeVasher, R.B., Moore, L.S. and Shaughnessy, K.H. (2004) J. Org. Chem., 69, 7919-27.
186. Beller, M., Riermeier, T.H., Reisinger, C.P. and Herrmann, W.A. (1997) Tetrahedron Lett., 38, 2073-4.
187. Zim, D. and Buchwald, S.L. (2003) Org. Lett., 5, 2413-15.
188. Schnyder, A., Indolese, A.F., Studer, M. and Blaser, H.U. (2002) Angew. Chem. Int. Ed., 41, 3668-71.
189. Blaser, H.-U., Indolese, A., Naud, F., Nettekoven, U. and Schnyder, A. (2004) Adv. Synth. Catal., 346, 1583-98.
190. Stambuli, J.P., Kuwano, R. and Hartwig, J.F. (2002) Angew. Chem. Int. Ed., 41, 4746-8.
191. Viciu, M.S., Kissling, R.M., Stevens, E.D. and Nolan, S.P. (2002) Org. Lett., 4, 2229-31.
192. Viciu, M.S., Navarro, O., Germaneau, R.F., Kelly, R.A., III, Sommer, W., Marion, N., Stevens, E.D., Cavallo, L. and Nolan, S.P. (2004) Organometallics, 23, 1629-35.
193. Marion, N., Navarro, O., Mei, J., Stevens, E.D., Scott, N.M. and Nolan, S.P. (2006) J. Am. Chem. Soc., 12, 4101-11.
194. Marion, N., Ecarnot, E.C., Navarro, O., Amoroso, D., Bell, A. and Nolan, S.P. (2006) J. Org. Chem., 71, 3816-21.
195. Goossen, L.J., Paetzold, J., Briel, O., Rivas-Nass, A., Karch, R. and Kayser, B. (2005) Synlett, 275-8.
196. Oezdemir, I., Demir, S., Goek, Y., Cetinkaya, E. and Cetinkaya, B. (2004) J. Mol. Catal. A, 222, 97-102.
197. Bedford, R.B. and Cazin, C.S.J. (2002) GB A 2376946, 20021231.
198. Christmann, U., Pantazis, D.A., Benet-Buchholz, J., McGrady, J.E., Maseras, F. and Vilar, R. (2006) J. Am. Chem. Soc., 128, 6376-90;
199. Christmann, U., Vilar, R. and White, A.J.P. (2004) Chem. Commun., 11, 1294-5.
200. Gusev, O.V., Peganova, T.A., Kalsin, A.M., Vologdin, N.V., Petrovskii, P.V., Lyssenko, K.A., Tsvetkov, A.V. and Beletskaya, I.P. (2006) Organometallics, 25, 2750-60.
201. Gusev, O.V., Peganova, T.A., Kalsin, A.M., Vologdin, N.V., Petrovskii, P.V., Lyssenko, K.A., Tsvetkov, A.V. and Beletskaya, I.P. (2005) J. Organomet. Chem., 690, 1710-17.
202. Gajare, A.S., Toyota, K., Yoshifuji, M. and Ozawa, F. (2004) J. Org. Chem., 69, 6504-6.
203. Jiang, L. and Buchwald, S.L. (2004) Palladium-Catalyzed Aromatic Carbon-Nitrogen Bond Formation in Metal-Catalyzed Cross-Coupling Reactions, Wiley-VCH Verlag GmbH, pp. 699-760;
204. Stauffer, S.R. and Hartwig, J.F. (2003) J. Am. Chem. Soc., 125, 6977-85.
205. Kuwano, R., Utsunomiya, M. and Hartwig, J.F. (2002) J. Org. Chem., 6, 6479-86.
206. Anderson, K.W., Ikawa, T., Tundel, R.E. and Buchwald, S.L. (2006) J. Am. Chem. Soc., 128, 10694-5.
207. Flessner, T. and Doye, S. (1999) J. Prakt. Chem., 341, 186-90.
208. Li, L. and Navasero, N. (2006) Org. Lett., 8, 3733-6.
209. Basu, B., Das, P., Nanda, A.K., Das, S. and Sarkar, S. (2005) Synlett, 1275-8.
210. Schlummer, B. and Scholz, U. (2006) DE 102004056820 A1 20060601.
211. Schlummer, B. and Scholz, U. (2006) I. WO 2006056412 A1 20060601.
212. Jensen, T.A., Liang, X., Tanner, D. and Skjaerbaek, N. (2004) J. Org. Chem., 69, 4936-47.
213. Buchwald, S.L. and Anderson, K.W. (2006) WO 2006074315 A2 20060713.
214. Smith, C.J., Tsang, M.W.S., Holmes, A.B., Danheiser, R.L. and Tester, J.W. (2005) Org. Biomol. Chem., 3767-81.
215. Varma, R.S. and Ju, Y. (2005) Green Separation Processes, 53-87.
216. Cave, G.W.V., Raston, C.L. and Scott, J.L. (2001) Chem. Commun., 2159-69.
217. Stauffer, S.R. and Steinbeiser, M.A. (2005) Tetrahedron Lett., 46, 2571-5.
218. Grushin, V.V. and Alper, H. (1994) Chem. Rev., 94, 1047-62.
219. Harris, M.C., Huang, X. and Buchwald, S.L. (2002) Org. Lett., 4, 2885-8 ;
220. Buchwald, S.L. and Huang, X. (2001) Org. Lett., 3, 3417-19.
221. Maes, B.U.W., Loones, K.T.J., Hostyn, S., Diels, G. and Rombouts, G. (2004) Tetrahedron, 60, 11559-64.
222. Urgaonkar, S., Nagarajan, M. and Verkade, J.G. (2003) J. Org. Chem., 68, 452-9 ;
223. Parrish, C.A. and Buchwald, S.L. (2001) J. Org. Chem., 66, 3820-7;
224. Ali, M.H. and Buchwald, S.L. (2001) J. Org. Chem., 66, 2560-5.
225. Iwaki, T., Yasuhara, A. and Sakamoto, T. (1999) J. Chem. Soc. Perkin Trans., 1, 1505-10.
226. Anderson, K.W., Mendez-Perez, M., Priego, J. and Buchwald, S.L. (2003) J. Org. Chem., 68, 9563-73.
227. Tundel, R.E., Anderson, K.W. and Buchwald, S.L. (2006) J. Org. Chem., 71, 430-3.
228. Zhang, W. and Nagashima, T. (2006) J. Fluorine Chem., 127, 588-91.
229. Blaser, H.U., Brieden, W., Pugin, B., Spindler, F., Studer, M. and Togni, A. (2002) Top. Catal., 19, 3-16.
230. Roy, A.H. and Hartwig, J.F. (2003) J. Am. Chem. Soc., 125, 8704-5.
231. Paul, F., Patt, J. and Hartwig, J.F. (1995) Organometallics, 14, 3030-9.
232. Wagaw, S. and Buchwald, S.L. (1996) J. Org. Chem., 61, 7240-1.
233. Grasa, G.A., Viciu, M.S., Huang, J. and Nolan, S.P. (2001) J. Org. Chem., 66, 7729-37.
234. Charles, M.D., Schultz, P. and Buchwald, S.L. (2005) Org. Lett., 7, 3965-8.
235. Audisio, D., Messaoudi, S., Peyrat, J.-F., Brion, J.-D. and Alami, M. (2007) Tetrahedron Lett., 48, 6928-32.
236. Hooper, M.W., Utsunomiya, M. and Hartwig, J.F. (2003) J. Org. Chem., 68, 2861-73.
237. Messaoudi, S., Audisio, D., Brion, J.-D. and Alami, M. (2007) Tetrahedron, 63, 10202-10.
238. Zhang, H.Q., Xia, Z., Vasudevan, A. and Djuric, S.W. (2006) Tetrahedron Lett., 47, 4881-4.
239. Lakshman, M.K., Keeler, J.C., Hilmer, J.H. and Martin, J.Q. (1999) J. Am. Chem. Soc., 121, 6090-1 ;
240. Lakshman, M.K., Hilmer, J.H., Martin, J.Q., Keeler, J.C., Dinh, Y.Q.V., Ngassa, F.N. and Russon, L.M. (2001) J. Am. Chem. Soc., 123, 7779-87 ;
241. Lakshman, M.K. (2005) Curr. Org. Synth., 2, 83-112.
242. Michalik, D., Kumar, K., Zapf, A., Tillack, A., Arlt, M., Heinrich, T. and Beller, M. (2004) Tetrahedron Lett., 45, 2057-61.
243. Shen, Q. and Hartwig, J.F. (2006) J. Am. Chem. Soc., 128, 10028-9.
244. Surry, D.S. and Buchwald, S.L. (2007) J. Am. Chem. Soc., 129, 10354-5.
245. Lee, S., Jorgensen, M. and Hartwig, J.F. (2001) Org. Lett., 3, 2729-32.
246. Hartwig, J.F., Jorgensen, M. and Lee, S. (2001) WO 03/006420 A1, 12.7.2001.
247. Lee, D.-Y. and Hartwig, J.F. (2005) Org. Lett., 7, 1169-72.
248. Deng, B.-L., Lepoivre, J.A. and Lemiere, G. (1999) Eur.J. Org. Chem., 2683-8;
249. Mann, G., Hartwig, J.F., Driver, M.S. and Fernandez-Rivas, C. (1998) J. Am. Chem. Soc., 120, 827-8 ;
250. Wolfe, J.P., Ahman, J., Sadighi, J.P., Singer, R.A. and Buchwald, S.L. (1997) Tetrahedron Lett., 38, 6367-70.
251. Jaime-Figueroa, S., Liu, Y., Muchowski, J.M. and Putman, D.G. (1998) Tetrahedron Lett., 39, 1313-16.
252. Lim, C.W. and Lee, S.-g. (2000) Tetrahedron, 56, 5131-6.
253. Cioffi, C.L., Berlin, M.L. and Herr, R.J. (2004) Synlett, 841-5.
254. Anderson, K.W., Tundel, R.E., Ikawa, T., Altman, R.A. and Buchwald, S.L. (2006) Angew. Chem. Int. Ed., 45, 6523-7.
255. Piguel, S. and Legraverend, M. (2007) J. Org. Chem., 72, 7026-9.
256. Furuta, T., Kitamura, Y., Hashimoto, A., Fujii, S., Tanaka, K. and Kan, T. (2007) Org. Lett., 9, 183-6.
257. Klapars, A., Campos, K.R., Chen, C.-y., and Volante, R.P. (2005) Org. Lett., 7, 1185-8.
258. Wallace, D.J., Klauber, D.J., Chen, C.-y. and Volante, R.P. (2003) Org. Lett., 5, 4749-52.
259. Madar, D.J., Kopecka, H., Pireh, D., Pease, J., Pliushchev, M., Sciotti, R.J., Wiedeman, P.E. and Djuric, S.W. (2001) Tetrahedron Lett., 42, 3681-4;
260. Ghosh, A., Sieser, J.E., Riou, M., Cai, W. and Rivera-Ruiz, L. (2003) Org. Lett., 5, 2207-10.
261. McLaughlin, M., Palucki, M. and Davies, I.W. (2006) Org. Lett., 8, 3311-14.
262. Bolm, C. and Hildebrand, J.P. (2000) J. Org. Chem., 65, 169-75.
263. Zhu, Y.-M., Kiryu, Y. and Katayama, H. (2002) Tetrahedron Lett., 43, 3577-80;
264. Lebedev, Y., Khartulyari, A.S. and Voskoboynikov, A.Z. (2005) J. Org. Chem., 70, 596-602.
265. Evindar, G. and Batey, R.A. (2003) Org. Lett., 5, 133-6.
266. Wang, Z., Skerlj, R.T. and Bridger, G.J. (1999) Tetrahedron Lett., 40, 3543-6.
267. Bedford, R.B. and Betham, M. (2006) J. Org. Chem., 71, 9403-10.
268. Romero, M., Harrak, Y., Basset, J., Ginet, L., Constans, P. and Pujol, M.D. (2006) Tetrahedron, 62, 9010-16.
269. Neogi, A., Majhi, T.P., Mukhopadhyay, R. and Chattopadhyay, P. (2006) J. Org. Chem., 71, 3291-4.
270. Venkatesh, C., Sundaram, G.S.M., Ila, H. and Junjappa, H. (2006) J. Org. Chem., 71, 1280-3.
271. Fukushima, W., Kanbara, T. and Yamamoto, T. (2005) Synlett, 19, 2931-4.
272. Nandakumar, M.V. and Verkade, J.G. (2005) Angew. Chem. Int. Ed., 44, 3115-18.
273. Yang, J.-S., Liau, K.-L., Wang, C.-M. and Hwang, C.-Y. (2004) J. Am. Chem. Soc., 126(39), 12325-35.
274. Ackermann, L. (2005) Org. Lett., 7, 439-42.
275. Gunda, P., Russon, L.M. and Lakshman, M.K. (2004) Angew. Chem. Int. Ed., 43, 6372-7.
276. Loones, K.T.J., Maes, B.U.W., Dommisse, R.A. and Lemiere, G.L. (2004) Chem. Commun., 2466-7.
277. Queiroz, M.-J.R.P., Begouin, A., Ferreira, I.C.F.R., Kirsch, G., Calhelha, R.C., Barbosa, S. and Estevinho, L.M. (2004) Eur. J. Org. Chem., 17, 3679-85.
278. Inamoto, K., Katsuno, M., Yoshino, T., Suzuki, I., Hiroya, K. and Sakamoto, T. (2004) Chem. Lett., 33, 1026-7.
279. Damon, D.B., Dugger, R.W., Hubbs, S.E., Scott, J.M. and Scott, R.W. (2006) Org. Proc. Res. Dev., 10, 472-80.
280. Damon, D.B., Dugger, R.W. and Scott, R.W. (2002) WO 2002088085 A2, 30.4.2001.
281. Damon, D.B., Dugger, R.W. and Scott, R.W. (2002) WO 2002088069 A2, 30.4.2001.
282. Alcazar-Roman, L.M. and Hartwig, J.F. (2001) J. Am. Chem. Soc., 123, 12905-6;
283. Stambuli, J.P., Bühl, M. and Hartwig, J.F. (2002) J. Am. Chem. Soc., 124, 9346-7.
284. Yin, J., Rainka, M.P., Zhang, X.X. and Buchwald, S.L. (2002) J. Am. Chem. Soc., 124, 1162-3.
285. Green, J.C., Herbert, B.J. and Lonsdale, R. (2005) J. Organomet. Chem., 690, 6054-67.
286. Tagashira, J., Imao, D., Yamamoto, T., Ohta, T., Furukawa, I. and Ito, Y. (2005) Tetrahedron: Asymmetry, 16, 2307-14.
287. Kreis, M., Friedmann, C.J. and Bräse, S. (2005) Chem. Eur.J., 11, 7387-94.
288. Satoh, T., Miura, M. and Nomura, M. (2002) J. Organomet. Chem., 653, 161-6.
289. Fauvarque, J.F. and Jutand, A. (1979) J. Organomet. Chem., 177, 273-81;
290. Galarini, R., Musco, A., Pontellini, R. and Santi, R. (1992) J. Mol. Catal., 72, L11-13;
291. Kuwajima, I. and Nakamura, E. (1985) Acc. Chem. Res., 18, 181-7;
292. Kosugi, M., Hagiwara, I., Sumiya, T. and Migita, T. (1984) Bull. Chem. Soc. Jpn, 57, 242-6 ;
293. Kosugi, M., Negishi, Y., Kameyama, M. and Migita, T. (1985) Bull. Chem. Soc. Jpn, 58, 3383-4.
294. Semmelhack, M.F., Stauffer, R.D. and Rogerson, T.D. (1973) Tetrahedron Lett., 4519-22 ;
295. Millard, A.A. and Rathke, M.W. (1977) J. Am. Chem. Soc., 99, 4833-5.
296. Ciufolini, M.A., Qi, H.B. and Browne, M.E. (1988) J. Org. Chem., 53(17), 4149-51.
297. Hamann, B.C. and Hartwig, J.F. (1997) J. Am. Chem. Soc., 119, 12382-3;
298. Palucki, M. and Buchwald, S.L. (1997) J. Am. Chem. Soc., 119, 11108-9;
299. Satoh, T., Kawamura, Y., Miura, M. and Nomura, M. (1997) Angew. Chem. Int. Ed., 36, 1740-2.
300. Kawatsura, M. and Hartwig, J.F. (1999) J. Am. Chem. Soc., 121, 1473-8.
301. Lee, S., Beare, N.A. and Hartwig, J.F. (2001) J. Am. Chem. Soc., 123, 8410-11;
302. Jørgensen, M., Lee, S., Liu, X., Wolkowski, J.P. and Hartwig, J.F. (2002) J. Am. Chem. Soc., 124, 12557-65.
303. Hama, T., Liu, X. and Culkin, D.A. (2003) J. Am. Chem. Soc., 125, 11176-7.
304. Moradi, W.A. and Buchwald, S.L. (2001) J. Am. Chem. Soc., 123, 7996-8002.
305. Gaertzen, O. and Buchwald, S.L. (2002) J. Org. Chem., 67, 465-75.
306. Beare, N.A. and Hartwig, J.F. (2002) J. Org. Chem., 67, 541-55 ;
307. Shelby, Q., Kataoka, N., Mann, G. and Hartwig, J.F. (2000) J. Am. Chem. Soc., 122, 10718-19;
308. Stambuli, J.P., Stauffer, S.R., Shaughnessy, K.H. and Hartwig, J.F. (2001) J. Am. Chem. Soc., 123, 2677-8.
309. Fox, J.M., Huang, X., Chieffi, A. and Buchwald, S.L. (2000) J. Am. Chem. Soc., 122, 1360-70.
310. Nguyen, H.N., Huang, X. and Buchwald, S.L. (2003) J. Am. Chem. Soc., 125, 11818-19.
311. Djakovitch, L. and Kohler, K. (2000) J. Organomet. Chem., 606, 101-7.
312. Stauffer, S.R., Beare, N.A., Stambuli, J.P. and Hartwig, J.F. (2001) J. Am. Chem. Soc., 123, 4641-2.
313. Ehrentraut, A., Zapf, A. and Beller, M. (2002) Adv. Synth. Catal., 344, 209-17.
314. Terao, Y., Satoh, T., Miura, M. and Nomura, M. (1998) Tetrahedron Lett., 39, 6203-6.
315. Terao, Y., Kametani, Y., Wakui, H., Satoh, T., Miura, M. and Nomura, M. (2001) Tetrahedron, 57, 5967-74.
316. Muratake, H., Natsume, M. and Nakai, H. (2004) Tetrahedron, 60, 11783-803.
317. Ackermann, L., Spatz, J.H., Gschrei, C.J., Born, R. and Althammer, A. (2006) Angew. Chem. Int. Ed., 45, 7627-30.
318. Shaughnessy, K.H., Hamann, B.C. and Hartwig, J.F. (1998) J. Org. Chem., 63, 6546-53.
319. Porcs-Makkay, M., Volk, B., Kapiller-Dezsofi, R., Mezei, T. and Simig, G. (2004) Monatsh. Chem., 135, 697-711.
320. Lee, S. and Hartwig, J.F. (2001) J. Org. Chem., 66, 3402-15.
321. Satoh, T., Inoh, J.-i., Kawamura, Y., Kawamura, Y., Miura, M. and Nomura, M. (1998) Bull. Chem. Soc.Jpn, 71, 2239-46.
322. Culkin, D.A. and Hartwig, J.F. (2002) J. Am. Chem. Soc., 124, 9330-1.
323. Wu, L. and Hartwig, J.F. (2005) J. Am. Chem. Soc., 127, 15824-32.
324. You, J. and Verkade, J.G. (2003) J. Org. Chem., 68, 8003-7.
325. Klapars, A., Waldman, J.H., Campos, K.R., Jensen, M.S., McLaughlin, M., Chung, J.Y.L., Cvetovich, R.J. and Chen, C.-yi (2005) J. Org. Chem., 70, 10186-9.