Palladium-catalyzed reactions using NHC ligands

Topics in Organometallic Chemistry

Volumn 21, Issue , 2006, Pages 47-82

  Díez González, Silvia ^a   Nolan, Steven P ^a  

^a UNIVERSITY OF NEW ORLEANS   (United States)

Author keywords

Catalysis; Cross coupling reaction; N heterocyclic carbene; Palladium

Indexed keywords

EID: 33750109251     PISSN: 14366002     EISSN: None     Source Type: Book Series    
DOI: 10.1007/3418_026     Document Type: Review

References (233)

1. Tsuji J (2000) Transition Metal Reagents and Catalysts. Wiley, New York
2. Trost BM, Verhoven TR (1982) In: Wilkinson G, Stone FG, Abel EW (eds) Comprehensive Organometallic Chemistry. Pergamon, Oxford, p 799
3. Heck RF (1985) Palladium Reagents in Organic Synthesis. Academic Press, New York
4. Pignolet LH (1983) Homogeneous Catalysis with Metal Phosphine Complexes. Plenum, New York
5. Wanzlick HW (1962) Angew Chem 74:129
6. Wanzlick HW, Esser F, Kleiner HJ (1963) Chem Ber 96:1208
7. Öfele K (1968) J Organomet Chem 12:P42
8. Wanzlick H-W, Schönherr H-J (1968) Angew Chem Int Ed Engl 7:141
9. Öfele K (1970) Angew Chem Int Ed Engl 9:739
10. Öfele K (1970) J Organomet Chem 22:C9
11. Arduengo AJ III, Harlow RL, Kline M (1991) J Am Chem Soc 113:361
12. Green JC, Scur RG, Arnold PL, Cloke GN (1997) Chem Commun 20:1963
13. Hermann WA (2002) Angew Chem Int Ed 41:1291
14. Lebel H, Janes MK, Charette AB, Nolan SP (2004) J Am Chem Soc 126:5046
15. Tsuji J, Takahashi H, Morikawa M (1965) Tetrahedron Lett 6:4387
16. Tsuji J (1969) Acc Chem Res 2:144
17. Hata G, Takahashi K, Miyate A (1970) J Chem Soc, Chem Commun 21:1392
18. Atkins KE, Walker WE, Manyik RM (1970) Tetrahedron Lett 11:3821
19. Sato Y, Yoshino T, Mori M (2003) Org Lett 5:31
20. Bonnet LG, Douthwaite RE (2003) Organometallics 22:4187
21. Gardiner MG, Herrmann WA, Reisinger C-P, Schwarz J, Spiegler M (1999) J Organomet Chem 572:239
22. McGuinness DS, Cavell KJ (2000) Organometallics 19:4918
23. Chen JCC, Lin IJB (2000) Organometallics 19:5113
24. Okuyama K-i, Sugiyama J-i, Nagahata R, Asai M, Ueda M, Takeuchi K (2003) J Mol Catal A: Chem 203:21
25. Okuyama K-i, Sugiyama J-i, Nagahata R, Asai M, Ueda M, Takeuchi K (2003) Macromolecules 36:6953
26. Suzuki A (1998) In: Diedrich F, Stang PJ (eds) Metal-catalyzed Cross-coupling Reactions. Wiley, Weinheim, p 49
27. Fürstner A, Seidel G (2002) Org Lett 4:541
28. Ma Y, Song C, Jiang W, Xue G, Cannon JF, Wang X, Andrus MB (2003) Org Lett 5:4635
29. Culkin DA, Hartwig JF (2003) Acc Chem Res 36:234
30. Viciu MS, Navarro O, Germaneau RF, Kelly RA III, Sommer W, Marion N, Stevens ED, Cavallo L, Nolan SP (2004) Organometallics 23:1629
31. Viciu MS, Germaneau RF, Navarro-Fernandez O, Stevens ED, Nolan SP (2002) Organometallics 21:5470
32. Viciu MS, Germaneau RF, Nolan SP (2002) Org Lett 4:4053
33. Navarro O, Marion N, Scott NM, González J, Amoroso D, Bell A, Nolan SP (2005) Tetrahedron 61:9716
34. Lee S, Beare NA, Hartwig JF (2001) J Am Chem Soc 123:8410
35. Lee S, Hartwig JF (2001) J Org Chem 66:3402
36. Cuifolini MA, Browne ME (1987) Tetrahedron Lett 28:171
37. Quallich, Makoski TW, Sanders AF, Urban FJ, Vazquez E (1998) J Org Chem 63:4116
38. Hirayama T, Kamada M, Tsurimi H, Mimura M (1976) Chem Pharm Bull 24:26
39. Lang SA, Lovell FM, Cohen E (1977) J Heterocycl Chem 14:65
40. Tsubata Y, Suzuki T, Miyashi T (1992) J Org Chem 57:6749
41. Gao C, Tao X, Qian Y, Huang J (2003) Chem Commun 1444
42. Uno M, Seto K, Masuda M, Ueda W, Takahashi S (1984) J Chem Soc, Chem Commun 932
43. Uno M, Seto K, Takahashi S (1985) Tetrahedron Lett 26:1553
44. Sakamoto T, Katoh E, Kondo Y, Yamanaka H (1988) Chem Pharm Bull 36:1664
45. Suzuki H, Kobayashi T, Osuka A (1983) Chem Lett 589
46. Okurro K, Furuune M, Miura M, Nomura M (1993) J Org Chem 58:7606
47. Cristau HJ, Vogel R, Taillefer M, Gadras A (2000) Tetrahedron Lett 41:8457
48. Gao CW, Tao XC, Lui TP, Huang JL, Qian Y (2002) Chin J Chem 20:819
49. Herrmann WA, Elison M, Fisher J, Köcher C, Artus GRJ (1995) Angew Chem Int Ed Eng 34:2371
50. Herrmann WA, Reisinger C-P, Spiegler M (1998) J Organomet Chem 557:93
51. Magill AM, McGuinness DS, Cavell KJ, Britovsek GJP, Gibson VC, White AJP, Williams DJ, White AH, Skelton BW (2001) J Organomet Chem 617:546
52. Peris E, Loch JA, Mata J, Crabtree RH (2001) Chem Commun 201
53. Selvakumar K, Zapf A, Spannenberg A, Beller M (2002) Chem Eur J 8:3901
54. Gürbüz N, Özdemir I, Demir S, Çentinkaya B (2004) J Mol Catal A: Chem 209:23
55. Lee HM, Lu CY, Chem CY, Chen WL, Lin HC, Chiu PL, Cheng PY (2004) Tetrahedron 60:5807
56. Huynh HV, Ho JHH, Neo TC, Koh LL (2005) J Organomet Chem 690:3854
57. Özdemir I, Demir S, Çetinkaya B (2005) Tetrahedron 61:9791
58. Shi M, Qian H-X (2005) Tetrahedron 61:4949
59. Herrmann WA, Öfele K, Preysing DV, Scheider SK (2003) J Organomet Chem 687:229
60. Frey GD, Schütz J, Herdweck E, Herrmann WA (2005) Organometallics 24:4416
61. Tubaro C, Biffis A, Basato M, Benetollo F, Cavell KJ, Ooi L-L (2005) Organometallics 24:4153
62. Schönfelder D, Fisher K, Schimdt M, Nuyken O, Weberskirch R (2005) Macromolecules 38:254
63. Fukuyama T, Arai M, Matsubara H, Ryu I (2004) J Org Chem 69:8105
64. Jin C-M, Twamley B, Shreeve JM (2005) Organometallics 24:3020
65. Gallo V, Mastrorilli P, Nobile CF, Paolillo R, Taccardi N (2005) Eur J Inorg Chem 582
66. Scharz J, Böhm VPW, Gardiner MG, Grosche M, Herrmann WA, Hieringer W, Raudaschl-Sieber G (2000) Chem Eur J 6:1773
67. Albert K, Gisdakis P, Rösch N (1998) Organometallics 17:1608
68. Yang C, Lee HM, Nolan SP (2001) Org Lett 3:1511
69. Herrmann WA, Böhm VPW, Gstöttmayr CWK, Grosche M, Reisinger C-P, Weskamp T (2001) J Organomet Chem 617618:616
70. Wang A-E, Xie J-H, Wang L-X, Zhou Q-L (2005) Tetrahedron 61:259
71. Yang C, Nolan SP (2001) Synlett 1539
72. Selvakumar K, Zapf A, Beller M (2002) Org Lett 4:3031
73. Andreus MB, Song C, Zhang J (2002) Org Lett 4:2079
74. Andrus MB, Liu J, Meredith EL, Nartey E (2003) Tetrahedron Lett 44:4819
75. Renaud S, De Lorgeril M (1992) Lancet 339:1523
76. Bachelor FW, Loman AA, Snowdon LR (1970) Can J Chem 48:1554
77. Alonso E, Ramon DJ, Yus M (1997) J Org Chem 62:417
78. Yu J, Gaunt MJ, Spencer JB (2002) J Org Chem 67:4627
79. Caló V, Nacci A, Monopoli A, Spinelli M (2003) Eur J Org Chem 1382
80. Dearden JC, Nicholson RM (1984) J Pharm Pharmacol 36:713
81. Ducki S, Hadfield JA, Hepworth LA, Lawrence NJ, Liu C-J (1997) Bioorg Med Chem Lett 7:3091
82. Murthy YVSN, Meah Y, Massey V (1999) J Am Chem Soc 121:5344
83. Calò V, Nacci A, Monopoli A, Lopez L, di Cosmo A (2001) Tetrahedron 57:6071
84. Calò V, Nacci A, Lopez L, Napola A (2001) Tetrahedron Lett 42:4701
85. Chuit C, Corriu RJP, Reya C, Young JC (1993) Chem Rev 93:1317
86. Horn KA (1995) Chem Rev 95:1317
87. Gouda K, Hagiwara E, Hatanaka Y, Hiyama T (1996) J Org Chem 61:7232
88. Hagiwara E, Gouda K, Hatanaka Y, Hiyama T (1997) Tetrahedron Lett 38:439
89. Hatanaka Y, Goda K, Hiyama T (1994) Tetrahedron Lett 35:1279
90. Lee HM, Nolan SP (2000) Org Lett 2:2053
91. Miyaura N, Suzuki A (1995) Chem Rev 95:2457
92. Dua SS, Howells RD, Gilman H (1974) 4:381
93. Meyers AI, Williams BE (1978) Tetrahedron Lett 19:223
94. Meyers AI, Nelson TD, Moorlag H, Rawson DJ, Meier A (2004) Tetrahedron 60:4459
95. Tamao K, Sumitani K, Kumada M (1972) J Am Chem Soc 94:4374
96. Corriu RJP, Masse JP (1972) J Chem Soc, Chem Commun 23:144
97. Yamamura M, Moritani I, Murahashi S (1975) J Organomet Chem 91:C39
98. Huang J, Nolan SP (1999) J Am Chem Soc 121:9889
99. Frisch AC, Rataboul F, Zapf A, Beller M (2003) J Organomet Chem 687:403
100. Devasagayaraj A, Stüdermann T, Knochel P (1995) Angew Chem Int Ed Engl 34:2723
101. Giovanni R, Stüdermann T, Dussin G, Knochel P (1998) Angew Chem Int Ed 37:2387
102. Giovanni R, Stüdermann T, Devasagayarj A, Dussin G, Knochel P (1999) J Org Chem 64:3544
103. Jensen AE, Knochel P (2002) J Org Chem 67:79
104. Zhou J, Fu GC (2003) J Am Chem Soc 125:14726
105. Hadei N, Kantchev EAB, O'Brien CJ, Organ MG (2005) Org Lett 7:3805
106. Nicolau KC, Sorensen EJ (1996) Classics in Total Synthesis. Wiley, Weinheim, p 582
107. Rusanov AL, Khotina IA, Begretov MM (1997) Russ Chem Rev 66:1053
108. Brandsma L, Vasilevsky SF, Verkruijse HD (1998) Application of Transition Metal Catalysis in Organic Synthesis. Springer, Berlin Heidelberg New York, p 179
109. Hermann WA, Reisinger C-P, Spiegler M (1998) J Organomet Chem 557:93
110. McGuiness DS, Cavell KJ (2000) Organometallics 19:741
111. Herrmann WA, Böhm VPW, Gstöttmayr CWK, Grosche M, Reisinger C-P,Weskamp T (2001) J Organomet Chem 617618:616
112. Yang C, Nolan SP (2002) Organometallics 21:1020
113. Ma Y, Song C, Quansheng W, Wang Y, Liu X, Andrus MB (2003) Org Lett 5:3317
114. Mas-Marzá E, Segarra AM, Claver C, Peris E, Fernández E (2003) Tetrahedron Lett 44:6595
115. Batey RA, Shen M, Lough AJ (2002) Org Lett 4:1411
116. Eckhardt M, Fu GC (2003) J Am Chem Soc 125:13642
117. Stille JK (1986) Angew Chem Int Ed Engl 25:508
118. Littke AF, Fu GC (2002) Angew Chem Int Ed 41:4176
119. Hassan J, Sévignon M, Gozzi C, Sultz E, Lemaire M (2002) Chem Rev 102:1359
120. Weskamp T, Böhm VPW, Herrmann WA (1999) J Organomet Chem 585:348
121. Grasa GA, Nolan SP (2001) Org Lett 3:119
122. Herrman WA, Reisinger C-P, Speingler M (1998) J Organomet Chem 557:93
123. Zhang C, Huang J, Trudell ML, Nolan SP (1999) J Org Chem 64:3804
124. Andrus MB, Song C (2001) Org Lett 3:3761
125. Gstöttmayr CWR, Böhm VPW, Herdtweck E, Grosche M, Herrmann WA (2002) Angew Chem Int Ed 41:1363
126. Navarro O, Oonishi Y, Kelly RA III, Stevens ED, Briel O, Nolan SP (2004) J Organomet Chem 689:3722
127. Singh R, Viciu MS, Kramareva N, Navarro O, Nolan SP (2005) Org Lett 7:1829
128. Song C, Ma Y, Chai Q, Ma C, Jiang W, Andrus MB (2005) Tetrahedron 61:7438
129. Wang A-E, Zhong J, Xie J-H, Li K, Zhou Q-L (2004) Adv Synth Catal 346:595
130. Liu D, Gao W, Dai Q, Zhang X (2005) Org Lett 7:4907
131. Zhao Y, Zhou Y, Ma D, Liu J, Li L, Zhang TY, Zhang H (2003) Organic & Biomolecular Chemistry 1:1643
132. Özdemir I, Gök Y, Gürbüz N, Çetinkaya E, Çetinkaya B (2004) Heteroaromatic Chem 15:419
133. Özdemir I, Gök Y, Gürbüz N, Çetinkaya E, Çetinkaya B (2004) Synth Commun 34:4135
134. McLachlan F, Mathews CJ, Smith PJ, Welton T (2003) Organometallics 22:5350
135. Kim J-H, Jun B-J, Byun J-W, Lee Y-S (2004) Tetrahedron Lett 45:5827
136. Kim J-H, Kim J-W, Shokouhimehr M, Lee Y-S (2005) J Org Chem 70:6714
137. Fürstner A, Leitner A (2001) Synlett 290
138. Grasa GA, Viciu MS, Huang J, Zhang C, Trudell ML, Nolan SP (2002) Organometallics 21:2866
139. Shi M, Qian H-X (2005) Appl Organomet Chem 19:1083
140. Llu J, Robins MJ (2005) Org Lett 7:1149
141. Altenhoff G, Goddard R, Lehmann CW, Glorius F (2003) Angew Chem Int Ed 42:3690
142. Altenhoff G, Goddard R, Lehmann CW, Glorius F (2004) J Am Chem Soc 126:15195
143. Walker SD, Barder TE, Martinelli JR, Buchwald SL (2004) Angew Chem Int Ed 116:1871
144. Navarro O, Kelly RA III, Nolan SP (2003) J Am Chem Soc 125:16104
145. Jiang L, Buchwald SL (1998) In: De Meijere A, Dietrich F (eds) Metal-catalyzed Cross-coupling Reactions. Wiley, Weinheim, p 725
146. Huang J, Grasa GA, Nolan SP (1999) Org Lett 1:1307
147. Stauffer SR, Lee S, Stambuli JP, Hauck SI, Hartwig JF (2000) Org Lett 2:1423
148. Grasa GA, Viciu MS, Huang J, Nolan SP (2001) J Org Chem 66:7729
149. Caddick S, Cloke FGN, Clentsmith GKB, Hitchcock PB, McKerrecher D, Titcomb LR, Williams MRV (2001) J Organomet Chem 617618:635
150. Titcomb LR, Caddick S, Cloke FGN, Wilson DJ, McKerrecher D (2001) Chem Commun 1388
151. Arentsen K, Caddick S, Cloke FGN (2005) Tetrahedron 61:9710
152. Viciu MS, Kissling RM, Stevens ED, Nolan SP (2002) Org Lett 4:2229
153. Viciu MS, Kelly RA III, Stevens ED, Naud F, Studer M, Nolan SP (2003) Org Lett 5:1479
154. McCarrol AJ, Sandham DA, Titcomb LR, Lewis AKK, Cloke FGN, Davies BP, Perez de Santana A, Hiller W, Caddick S (2003) Molecular Diversity 7:115
155. Özdemir I, Demir S, Gök Y, Çetinkaya E, Çetinkaya B (2004) J Mol Catal A: Chem 222:97
156. Schoenberg A, Bartoletti I, Heck RF (1974) J Org Chem 39:3318
157. Schoenberg A, Heck RF (1974) J Org Chem 39:3327
158. Ritter K (1993) Synthesis 735
159. Gaviño R, Pellegrini S, Castanet Y, Mortreux A, Mentre O (2001) Appl Catal A 217:91
160. Ma Y, Song C, Chai Q, Ma C, Andrus MB (2003) Synthesis 2886
161. Andrus MB, Ma Y, Zang Y, Song C (2002) Tetrahedron Lett 43:9137
162. Calò V, Giannoccaro P, Nacci A, Monopoli A (2002) J Organomet Chem 645:152
163. Gilchrist TL (1997) Heterocyclic Chemistry. Addison-Wesley Longman, Singapore
164. Ackermann L (2005) Org Lett 7:439
165. Cheung WS, Patch RJ, Player MR (2005) J Org Chem 70:3741
166. Hudlicky M (1991) In: Trost BM, Fleming I (eds) Comprehensive Organic Synthesis, vol 8. Pergamon, Oxford, p 895
167. Viciu MS, Grasa GA, Nolan SP (2001) Organometallics 20:3607
168. Navarro O, Kaur H, Mahjoor P, Nolan SP (2004) J Org Chem 69:3173
169. Muehlhofer M, Strassner T, Herrmann WA (2002) Angew Chem Int Ed 41:1745
170. Strassner T, Muehlhofer M, Zeller A, Herdtweck E, Herrmann WA (2004) J Organomet Chem 689:1418
171. Kakiuchi F, Murai S (2002) Acc Chem Res 35:826
172. Miura M, Nomura M (2002) Top Curr Chem 219:211
173. Campeau L-C, Thansandote P, Fagnou K (2005) Org Lett 7:1857
174. Gürbüz N, Özdemir I, Çetinkaya B (2005) Tetrahedron Lett 46:2273
175. Fujiwara Y, Jintoku T, Takaki K (1990) CHEMTECH 636
176. Trost BM (1991) Science 278:1471
177. Shilov E, Shul'pin GB (1997) Chem Rev 9:2879
178. Dyker G (1999) Angew Chem Int Ed 38:1698
179. Jia C, Lu W, Oyamada J, Kitamura T, Matsuda K, Irie M, Fujiwara Y (2000) J Am Chem Soc 122:7252
180. Jia C, Piao D, Oyamada J, Lu W, Kitamura T, Fujiwara Y (2000) Science 287:1992
181. Jia C, Kitamura T, Fujiwara Y (2001) Acc Chem Res 34:633
182. Viciu MS, Stevens ED, Petersen JL, Nolan SP (2004) Organometallics 23:3752
183. Aubert C, Buisine O, Malacria M (2002) Chem Rev 102:813
184. Diver ST, Geissert AJ (2004) Chem Rev 104:1317
185. Beletskaya I, Moberg C (1999) Chem Rev 99:3435
186. Suginome M, Ito Y (2000) Chem Rev 100:3221
187. Sato Y, Imakuni N, Mori M (2003) Adv Synth Catal 345:488
188. Lautens M, Mancuso J (2002) Synlett 394
189. Sato Y, Imakuni N, Hirose T, Wakamatsu H, Mori M (2003) J Organomet Chem 687:392
190. McGuinness DS, Cavell KJ, Skelton BW, White AH (1999) Organometallics 18:1596
191. Clement ND, Cavell KJ, Jones C, Elsevier CJ (2004) Angew Chem Int Ed 43:1277
192. Sprengers JW, Wassenaar J, Clement ND, Cavell KJ, Elseiver CJ (2005) Angew Chem Int Ed 44:2026
193. van Laren MW, Elseiver CJ (1999) Angew Chem Int Ed 38:3715
194. van Laren MW, Elseiver CJ (1999) Angew Chem Int Ed 38:3926
195. Dess DB, Martin JC (1983) J Org Chem 48:4155
196. Harding KE, May LM, Dick KF (1975) J Org Chem 40:1664
197. Corey EJ, Schmidt G (1975) Tetrahedron Lett 26:2647
198. Nishimura T, Onoue M, Ohe K, Uemura S (1999) J Org Chem 64:6750
199. ten Brink G-J, Arends IWCE, Sheldon RA (2000) Science 287:1636
200. Iwasawa T, Tokunaga M, Obora T, Tsuji Y (2004) J Am Chem Soc 126:6554
201. Jensen DR, Schultz MJ, Mueller JA, Sigman MS (2003) Angew Chem Int Ed 42:3810
202. Schultz MJ, Hamilton SS, Jensen DR, Sigman MS (2005) J Org Chem 70:3343
203. Nielson RJ, Keith JM, Stoltz BM, Goddard WA III (2004) J Am Chem Soc 126:7967
204. Mueller JA, Goller CP, Sigman MS (2004) J Am Chem Soc 126:9724
205. Steinhoff BA, Guzei IA, Stahl SS (2004) J Am Chem Soc 126:11268
206. Konnick MM, Guzei IA, Stahl SS (2004) J Am Chem Soc 126:10212
207. Smidt J (1962) Chem Ind 54
208. Tsuji J (1984) Synthesis 5:369
209. Takacs JM, Jiang X-T (2003) Curr Org Chem 7:369
210. Cornell CN, Sigman MS (2005) J Am Chem Soc 127:2796
211. Namboodirl VV, Varma RS, Sasle-Demessie E, Pillai UR (2002) Green Chem 4:170
212. Alandis N, Rico-Lattes I, Lattes A (1994) New J Chem 18:1147
213. Tsuji J (1995) Palladium Reagents and Catalyst. Wiley, Chichester, p 19
214. Henry PM (2002) In: Negishi E (ed) Handbook of Organopalladium Chemistry for Organic Chemistry. Wiley, New York, p 2219
215. Muñiz K (2004) Adv Synth Catal 346:1425
216. Keim W, Behr A, Röper M (1982) In: Wilkinson G, Stone FGA, Abel EW (eds) Comprehensive Organometallic Chemistry. Pergamon Press, Oxford, p 372
217. Behr A (1984) In: Ugo R (ed) Aspects of Homogeneous Catalysis, vol 5. Reidel, Dordrecht.
218. Sheldon RA (2000) Pure Appl Chem 72:1233
219. Tsuji J, Yasuda H, Mandai T (1978) J Org Chem 43:3606
220. Tsuji J, Kobayashi Y, Takahasi T (1980) Tetrahedron Lett 21:483
221. Falbe J, Bahrmann H, Lipps W, Mayer D (1985) In: Gerhartz W, Yamamoto YS, Campbell FT, Pfefferkorn R, Rounsaville JF (eds) Ullman's Encyclopedia of Industrial Chemistry, vol A1. VCH, Weinheim
222. Jolly PW (1985) Angew Chem Int Ed Engl 24:283
223. Vollmuller F, Krause J, Klein S, Magerlein W, Beller M (2000) Eur J Inorg Chem 1825
224. Krause J, Haack K-J, Cestaric G, Goddard R, Pörschke (1998) Chem Commun 1291
225. Jackstell R, Gómez Andeu M, Frisch A, Selvakumar K, Zapf A, Klein H, Spannenberg A, Röttger D, Briel O, Karch R, Beller M (2002) Angew Chem Int Ed 41:986
226. Gömez Andeu M, Zapf A, Beller M (2000) Chem Commun 2475
227. Vollmüller F, Mägerlein W, Klein S, Krause J, Beller M (2001) Adv Synth Catal 343:29
228. Jackstell R, Harkal S, Jiao H, Spannenberg A, Borgmann C, Röttger D, Nierlich F, Elliot M, Niven S, Cavell K, Navarro O, Viciu MS, Nolan SP, Beller M (2004) Chem Eur J 10:3891
229. Harkal S, Jackstell R, Nierlich F, Ortmann D, Beller M (2005) Org Lett 7:541
230. Pantukh BI, Egoricheva SA, Shulmanas (2000) RU Patent 2160285
231. Collins DJ, Bryn H, Kwan WP, Marie BS (1996) Int Patent WO 9621474
232. Brown HC, Negishi E (1969) J Am Chem Soc 91:1224
233. Viciu MS, Zinn FK, Stevens ED, Nolan SP (2003) Organometallics 22:3175