Microwave-assisted and metal-catalyzed coupling reactions

Topics in Current Chemistry

Volumn 266, Issue , 2006, Pages 103-144

  Nilsson, P ^a   Olofsson, K ^a   Larhed, M ^b  

^a Biolipox AB   (Sweden)

^b UPPSALA UNIVERSITY   (Sweden)

Author keywords

Buchwald Hartwig; Cross coupling; Heck; Homogeneous catalysis; Microwave; Sonogashira

Indexed keywords

EID: 33748987091     PISSN: 03401022     EISSN: None     Source Type: Book Series    
DOI: 10.1007/128_046     Document Type: Review

References (164)

1. Mingos DMP, Baghurst DR (1991) Chem Soc Rev 20:1
2. Lidström P, Tierney J, Wathey B, Westman J (2001) Tetrahedron 57:9225
3. Loupy A (2002) Microwaves in organic synthesis. Wiley, Weinheim
4. Kappe CO (2004) Angew Chem Int Ed 43:6250
5. Kappe CO, Stadler A (2005) Microwaves in organic and medicinal chemistry. Wiley, Weinheim
6. Kuznetsov DV, Raev VA, Kuranov GL, Arapov OV, Kostikov RR (2005) Russ J Org Chem 41:1719
7. Strauss CR, Trainor RW (1995) Aust J Chem 48:1665
8. Larhed M, Moberg C, Hallberg A (2002) Acc Chem Res 35:717
9. Leadbeater NE (2005) Chem Commun p 2881
10. Roberts BA, Strauss CR (2005) Acc Chem Res 38:653
11. Gronnow MJ, White RJ, Clark JH, Macquarrie DJ (2005) Org Process Res Dev 9:516
12. Larhed M, Hallberg A (2001) Drug Discov Today 6:406
13. Lew A, Krutzik PO, Hart ME, Chamberlin AR (2002) J Comb Chem 4:95
14. Baxendale IR, Lee AL, Ley SV (2005) In: Tierney JP, Lidström P (eds) Microwave assisted organic synthesis. Blackwell, Oxford, UK, p 133
15. Kappe CO, Dallinger D (2006) Nat Rev Drug Discovery 5:51
16. Sarko CR (2005) In: Tierney JP, Lidström P (eds) Microwave assisted organic synthesis. Blackwell, Oxford, p 222
17. Cornils B, Herrmann WA (eds) (2002) Applied homogeneous catalysis with organometallic compounds, vol 3: Developments, 2nd edn. Wiley, Weinheim
18. Tucker CE, de Vries JG (2002) Top Catal 19:111
19. Negishi E-i (2002) Handbook of organopalladium chemistry for organic synthesis, vol 1. Wiley, New York
20. Ley SV, Thomas AW (2003) Angew Chem Int Ed 42:5400
21. Olofsson K, Larhed M (2005) In: Tierney JP, Lidström P (eds) Microwave assisted organic synthesis. Blackwell, Oxford, p 23
22. Olofsson K, Hallberg A, Larhed M (2002) In: Loupy A (ed) Microwaves in organic synthesis. Wiley, Weinheim, p 379
23. Beller M, Cornils B, Frohning CD, Kohlpaintner CW (1995) J Mol Catal A 104:17
24. Morimoto T, Kakiuchi K (2004) Angew Chem Int Ed 43:5580
25. Skoda-Földes R, Kollár L (2002) Curr Org Chem 6:1097
26. Kaiser NFK, Hallberg A, Larhed M (2002) J Comb Chem 4:109
27. Wannberg J, Larhed M (2003) J Org Chem 68:5750
28. Georgsson J, Hallberg A, Larhed M (2003) J Comb Chem 5:350
29. Herrero MA, Wannberg J, Larhed M (2004) Synlett 2335
30. Lagerlund O, Larhed M (2006) J Comb Chem 8:4
31. Wan YQ, Alterman M, Larhed M, Hallberg A (2003) J Comb Chem 5:82
32. Marradi M (2005) Synlett 1195
33. Wu X, Wannberg J, Larhed M (2006) Tetrahedron 62:4665
34. Wannberg J, Dallinger D, Kappe CO, Larhed M (2005) J Comb Chem 7:574
35. Sinou D (1999) Top Curr Chem 206:41
36. Li C-J (2005) Chem Rev 105:3095
37. Andrade CKZ, Alves LM (2005) Curr Org Chem 9:195
38. Wu X, Larhed M (2005) Org Lett 7:3327
39. Wu X, Ekegren JK, Larhed M (2006) Organometallics ASAP
40. Wu X, Nilsson P, Larhed M (2005) J Org Chem 70:346
41. Larhed M, Hallberg A (2002) In: Negishi E-i (ed) Handbook of organopalladium chemistry for organic synthesis, vol 1. Wiley, New York, p 1133
42. De Meijere A, Meyer FE (1994) Angew Chem Int Ed Engl 33:2379
43. Beletskaya IP, Cheprakov AV (2000) Chem Rev 100:3009
44. Larhed M, Hallberg A (1996) J Org Chem 61:9582
45. Nájera C, Botella L (2005) Tetrahedron 61:9688
46. Arvela RK, Leadbeater NE (2005) J Org Chem 70:1786
47. Vallin KSA, Emilsson P, Larhed M, Hallberg A (2002) J Org Chem 67:6243
48. Littke AF, Fu GC (2002) Angew Chem Int Ed 41:4176
49. Datta GK, Vallin KSA, Larhed M (2003) Mol Div 7:107
50. Stadler A, von Schenck H, Vallin KSA, Larhed M, Hallberg A (2004) Adv Synth Catal 346:1773
51. Svennebring A, Garg N, Nilsson P, Hallberg A, Larhed M (2005) J Org Chem 70:4720
52. Andappan MMS, Nilsson P, Larhed M (2003) Mol Div 7:97
53. Sonogashira K (2002) In: Negishi E-i (ed) Handbook of organopalladium chemistry for organic synthesis, vol 1. Wiley, New York, p 493
54. Kabalka GW, Wang L, Namboodiri V, Pagni RM (2000) Tetrahedron Lett 41:5151
55. Erdelyi M, Gogoll A (2001) J Org Chem 66:4165
56. Kabalka GW, Wang L, Pagni RM (2001) Tetrahedron 57:8017
57. Erdelyi M, Gogoll A (2003) J Org Chem 68:6431
58. Berthault A, Berteina-Raboin S, Finaru A, Guillaumet G (2004) QSAR Comb Sci 23:850
59. Xia M, Wang Y-G (2002) J Chem Res Synop p 173
60. Xia M, Wang YG (2002) Chin Chem Lett 13:1
61. Yan J, Wang Z, Wang L (2004) J Chem Res p 71
62. He H, Wu YJ (2004) Tetrahedron Lett 45:3237
63. Appukkuttan P, Dehaen W, Van der Eycken E (2003) Eur J Org Chem p 4713
64. Hopkins CR, Collar N (2004) Tetrahedron Lett 45:8631
65. Leadbeater NE, Marco M, Tominack BJ (2003) Org Lett 5:3919
66. Arvela RK, Leadbeater NE, Sangi MS, Williams VA, Granados P, Singer RD (2005) J Org Chem 70:161
67. Kohara Y, Kubo K, Imamiya E, Wada T, Inada Y, Naka T (1996) J Med Chem 39:5228
68. Liljebris C, Larsen SD, Ogg D, Palazuk BJ, Bleasdale JE (2002) J Med Chem 45:1785
69. Tschaen DM, Desmond R, King AO, Fortin MC, Pipik B, King S, Verhoeven TR (1994) Synth Commun 24:887
70. Alterman M, Hallberg A (2000) J Org Chem 65:7984
71. Arvela RK, Leadbeater NE (2003) J Org Chem 68:9122
72. Srivastava RR, Collibee SE (2004) Tetrahedron Lett 45:8895
73. Zhang A, Neumeyer JL (2003) Org Lett 5:201
74. Cai L, Liu X, Tao X, Shen D (2004) Synth Commun 34:1215
75. Arvela RK, Leadbeater NE, Torenius HM, Tye H (2003) Org Biomol Chem 1:1119
76. Leadbeater NE, Torenius HM, Tye H (2003) Tetrahedron 59:2253
77. Bengtson A, Hallberg A, Larhed M (2002) Org Lett 4:1231
78. Hartwig JF (1998) Angew Chem Int Ed 37:2046
79. Sharifi A, Hosseinzadeh R, Mirzaei M (2002) Monatsh Chem 133:329
80. Wan Y, Alterman M, Hallberg A (2002) Synthesis p 1597
81. Jensen TA, Liang X, Tanner D, Skjaerbaek N (2004) J Org Chem 69:4936
82. Tundel RE, Anderson KW, Buchwald SL (2006) J Org Chem 71:430
83. Maes BUW, Loones KTJ, Lemiere GLF, Dommisse RA (2003) Synlett 1822
84. Heo J-N, Song YS, Kim BT (2005) Tetrahedron Lett 46:4621
85. Brain CT, Steer JT (2003) J Org Chem 68:6814
86. Weigand K, Pelka S (2003) Mol Div 7:181
87. McCarroll AJ, Sandham DA, Titcomb LR, Lewis AKdK, Cloke FGN, Davies BP, Perez de Santana A, Hiller W, Caddick S (2003) Mol Div 7:115
88. Maes BUW, Loones KTJ, Hostyn S, Diels G, Rombouts G (2004) Tetrahedron 60:11559
89. Arvela RK, Leadbeater NE, Collins MJ (2005) Tetrahedron 61:9349
90. Stadler A, Yousefi BH, Dallinger D, Walla P, Van der Eycken E, Kaval N, Kappe CO (2003) Org Process Res Dev 7:707
91. Lehmann H, LaVecchia L (2005) Jala 10:412
92. Loones KTJ, Maes BUW, Rombouts G, Hostyn S, Diels G (2005) Tetrahedron 61:10338
93. Wu YJ, He H, L'Heureux A (2003) Tetrahedron Lett 44:4217
94. Combs AP, Saubern S, Rafalski M, Lam PYS (1999) Tetrahedron Lett 40:1623
95. Lange JHM, Hofmeyer LJF, Hout FAS, Osnabrug SJM, Verveer PC, Kruse CG, Feenstra RW (2002) Tetrahedron Lett 43:1101
96. Poondra RR, Turner NJ (2005) Org Lett 7:863
97. Pabba C, Wang HJ, Mulligan SR, Chen ZJ, Stark TM, Gregg BT (2005) Tetrahedron Lett 46:7553
98. He H, Wu YJ (2003) Tetrahedron Lett 44:3385
99. Burton G, Cao P, Li G, Rivero R (2003) Org Lett 5:4373
100. Harmata M, Hong XC, Ghosh SK (2004) Tetrahedron Lett 45:5233
101. Appukkuttan P, Dehaen W, Fokin VV, Van der Eycken E (2004) Org Lett 6:4223
102. Andersen J, Madsen U, Bjorkling F, Liang XF (2005) Synlett 2209
103. Manbeck GF, Lipman AJ, Stockland RA, Freidl AL, Hasler AF, Stone JJ, Guzei IA (2005) J Org Chem 70:244
104. He H, Wu YJ (2003) Tetrahedron Lett 44:3445
105. Villemin D, Jaffres PA, Simeon F (1997) Phos Sulf Silic Rel Elem 130:59
106. Villemin D, Elbilali A, Simeon F, Jaffres PA, Maheut G, Mosaddak M, Hakiki A (2003) J Chem Res Synop 436
107. Stadler A, Kappe CO (2002) Org Lett 4:3541
108. Wu YJ, He H (2003) Synlett 1789
109. Lengar A, Kappe CO (2004) Org Lett 6:771
110. Alexandre FR, Berecibar A, Wrigglesworth R, Besson T (2003) Tetrahedron Lett 44:4455
111. Besson T, Dozias MJ, Guillard J, Rees CW (1998) J Chem Soc Perkin Trans 1:3925
112. Marquie J, Laporterie A, Dubac J, Roques N, Desmurs JR (2001) J Org Chem 66:421
113. Grushin VV, Alper H (1994) Chem Rev 94:1047
114. Kabalka GW, Varma RS (1989) Tetrahedron 45:6601
115. Elander N, Jones JR, Lu SY, Stone-Elander S (2000) Chem Soc Rev 29:239
116. Arvela RK, Leadbeater NE (2003) Synlett 1145
117. Miyaura N, Suzuki A (1995) Chem Rev 95:2457
118. Ersmark K, Larhed M, Wannberg J (2004) Curr Opin Drug Discov 7:417
119. Comer E, Organ MG (2005) J Am Chem Soc 127:8160
120. Leadbeater NE, Marco M (2003) J Org Chem 68:888
121. Leadbeater NE, Marco M (2002) Org Lett 4:2973
122. Bai L, Wang JX, Zhang YM (2003) Green Chemistry 5:615
123. Bedford RB, Butts CP, Hurst TE, Lidstrom P (2004) Adv Synth Catal 346:1627
124. Navarro O, Kaur H, Mahjoor P, Nolan SP (2004) J Org Chem 69:3173
125. Miao GB, Ye P, Yu LB, Baldino CM (2005) J Org Chem 70:2332
126. Arvela RK, Leadbeater NE (2005) Org Lett 7:2101
127. Najera C, Gil-Molto J, Karlstrom S (2004) Adv Synth Catal 346:1798
128. Bai L, Wang JX (2004) Chin Chem Lett 15:286
129. Namboodiri VV, Varma RS (2001) Green Chem 3:146
130. Larhed M, Lindeberg G, Hallberg A (1996) Tetrahedron Lett 37:8219
131. Stadler A, Kappe CO (2001) Eur J Org Chem 2001:919
132. Wang Y, Sauer DR (2004) Org Lett 6:2793
133. Bai L, Zhang YM, Wang JX (2004) QSAR Comb Sci 23:875
134. Gil-Molto J, Karlström S, Najera C (2005) Tetrahedron 61:12168
135. Dawood KM, Kirschning A (2005) Tetrahedron 61:12121
136. Solodenko W, Schon U, Messinger J, Glinschert A, Kirschning A (2004) Synlett 1699
137. Gladysz JA, Curran DP, Horváth IT (eds) (2004) Handbook of fluorous chemistry. Wiley, Weinheim
138. Zhang W (2004) Chem Rev 104:2531
139. Zhang W, Chen CHT, Lu YM, Nagashima T (2004) Org Lett 6:1473
140. Lu YM, Zhang W (2004) QSAR Comb Sci 23:827
141. Zhang W, Chen CHT (2005) Tetrahedron Lett 46:1807
142. Song YS, Kim BT, Heo JN (2005) Tetrahedron Lett 46:5987
143. Coats SJ, Schulz MJ, Carson JR, Codd EE, Hlasta DJ, Pitis PM, Stone DJ Jr, Zhang S-P, Colburn RW, Dax SL (2004) Bioorg Med Chem Lett 14:5493
144. Mathews CJ, Taylor J, Tyte MJ, Worthington PA (2005) Synlett 538
145. Combs AP, Glass BM, Jackson SA (1999) Methods Enzymol 369:223
146. Organ MG, Mayer S, Lepifre F, N'Zemba B, Khatri J (2003) Mol Div 7:211
147. Ersmark K, Feierberg I, Bjelic S, Hamelink E, Hackett F, Blackman MJ, Hulten J, Samuelsson B, Åqvist J, Hallberg A (2004) J Med Chem 47:110
148. Nöteberg D, Hamelink E, Hultén J, Wahlgren M, Vrang L, Samuelsson B, Hallberg A (2003) J Med Chem 46:734
149. Nöteberg D, Schaal W, Hamelink E, Vrang L, Larhed M (2003) J Comb Chem 5:456
150. Espinet P, Echavarren AM (2004) Angew Chem Int Ed 43:4704
151. Kaval N, Dehaen W, Van der Eycken E (2005) J Comb Chem 7:90
152. Olofsson K, Kim SY, Larhed M, Curran DP, Hallberg A (1999) J Org Chem 64:4539
153. Maleczka RE Jr, Lavis JM, Clark DH, Gallagher WP (2000) Org Lett 2:3655
154. Larhed M, Hoshino M, Hadida S, Curran DP, Hallberg A (1997) J Org Chem 62:5583
155. Öhberg L, Westman J (2001) Synlett 1893
156. Walla P, Kappe CO (2004) Chem Commun p 564
157. Krascsenicsova K, Walla P, Kasak P, Uray G, Kappe CO, Putala M (2004) Chem Commun p 2606
158. Stanetty P, Schnurch M, Mihovilovic MD (2003) Synlett 1862
159. Mutule I, Suna E (2004) Tetrahedron Lett 45:3909
160. Mutule G, Suna E (2005) Tetrahedron 61:11168
161. Hassan J, Sevignon M, Gozzi C, Schulz E, Lemaire M (2002) Chem Rev 102:1359
162. Gold H, Larhed M, Nilsson P (2005) Synlett 1596
163. Hiyama T, Shirakawa E (2002) In: Negishi E-I (ed) Handbook of organopalladium chemistry for organic synthesis, vol 1. Wiley, New York, p 285
164. Clarke ML (2005) Adv Synth Catal 347:303