Recent advances in the Heck-Matsuda reaction in heterocyclic chemistry

Tetrahedron

Volumn 67, Issue 16, 2011, Pages 2815-2831

  Felpin, Franois Xavier ^a   Nassar Hardy, Luma ^a   Le Callonnec, François ^a   Fouquet, Eric ^a  

^a UNIVERSITÉ DE BORDEAUX   (France)

Author keywords

Aryl diazonium salts; Heck Matsuda reaction; Heterocycles; Natural products; Palladium

Indexed keywords

COUNTERION; DIAZONIUM COMPOUND; HETEROCYCLIC COMPOUND; NITROGEN DERIVATIVE; OXYGEN DERIVATIVE; PALLADIUM;

ARTICLE; ARYLATION; CHEMICAL REACTION; HECK MATSUDA REACTION; HECK REACTION; PRIORITY JOURNAL;

EID: 79953217003     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2011.02.051     Document Type: Review

References (157)

1. For selected reviews, see:
2. V. Farina Adv. Synth. Catal. 346 2004 1553 1582
3. H.-U. Blaser, A. Indolese, F. Naud, U. Nettekoven, and A. Schnyder Adv. Synth. Catal. 346 2004 1583 1598
4. A. Zapf, and M. Beller Chem. Commun. 2005 431 440
5. K.C. Nicolaou, P.G. Bulger, and D. Sarlah Angew. Chem. 117 2005 4516 4563
6. Angew. Chem., Int. Ed. 44 2005 4442 4489
7. G. Zeni, and R.C. Larock Chem. Rev. 106 2006 4644 4680
8. J.G. de Vries Can. J. Chem. 79 2001 1086 1092
9. T. Mizoroki, K. Mori, and A. Ozaki Bull. Chem. Soc. Jpn. 44 1971 581 582
10. R.F. Heck, and J.P. Nolley Jr. J. Org. Chem. 37 1972 2320 2322
11. I.P. Beletskaya, and A.V. Cheprakov Chem. Rev. 100 2000 3009 3066
12. N.J. Whitcombe, K.K. Hii, and S.E. Gibson Tetrahedron 57 2001 7449 7476
13. N.T.S. Phan, M. Van Der Sluys, and C.W. Jones Adv. Synth. Catal. 348 2006 609 679
14. V. Polshettiwar, and Á Molnár Tetrahedron 63 2007 6949 6976
15. The Nobel Prize in Chemistry 2010 was awarded jointly to Richard F. Heck, Ei-ichi Negishi and Akira Suzuki.
16. M.T. Reetz, and E. Westermann Angew. Chem., Int. Ed. 39 2000 165 168
17. M.T. Reetz, and J.G. de Vries Chem. Commun. 2004 1559 1563
18. D. Astruc, F. Lu, and J. Ruiz Aranzaes Angew. Chem., Int. Ed. 44 2005 7852 7872
19. D. Astruc Inorg. Chem. 46 2007 1884 1894
20. A.B. Dounay, and L.E. Overman Chem. Rev. 103 2003 2945 2963
21. M. Shibasaki, E.M. Vogl, and T. Ohshima Adv. Synth. Catal. 346 2004 1533 1552
22. B.L. Shaw, S.D. Perera, and E.A. Staley Chem. Commun. 1998 1361 1362
23. M. Ohff, A. Ohff, M.E. van der Boom, and D. Milstein J. Am. Chem. Soc. 119 1997 11687 11688
24. G.P.F. van Strijdonck, M.D.K. Boele, P.C.J. Kamer, J.G. de Vries, and P.W.N.M. Leewen Eur. J. Inorg. Chem. 1999 1073 1076
25. T. Rosner, J. Le Bars, A. Pfaltz, and D.G. Blackmond J. Am. Chem. Soc. 123 2001 1848 1855
26. W.A. Herrmann, C. Brossmer, K. Ofele, M. Beller, and H. Fischer J. Mol. Catal. A: Chem. 103 1995 133 146
27. W. Cabri, and I. Candiani Acc. Chem. Res. 28 1995 2 7
28. A. Roglans, A. Pla-Quintana, and M. Moreno-Mañas Chem. Rev. 106 2006 4622 4643
29. P. Griess Liebigs Ann. Chem. 106 1858 123 125
30. D.T. Flood Org. Synth. 2 1943 295 298
31. M. Barbero, M. Crisma, I. Degani, R. Fochi, and P. Perracino Synthesis 1998 1171 1175
32. C. Colas, and M. Goeldner Eur. J. Org. Chem. 1999 1357 1366
33. V.D. Filimonov, M. Trusova, P. Postnikov, E.A. Krasnokutskaya, Y.M. Lee, H.Y. Hwang, H. Kim, and K.-W. Chi Org. Lett. 10 2008 3961 3964
34. C. Romming Acta Chem. Scand. 17 1963 1444 1454
35. G. Schiemann, and W. Winkelmüller Org. Synth. 2 1943 299 302
36. M.P. Doyle, and W.J. Bryker J. Org. Chem. 44 1979 1572 1574
37. S. Bhattacharya, S. Majee, R. Mukherjee, and S. Sengupta Synth. Commun. 25 1995 651 657
38. S. Sengupta, and S.K. Sadhukhan Org. Synth. 10 2004 263 266
39. S. Bräse, and M. Schroen Angew. Chem., Int. Ed. 38 1999 1071 1073
40. M.P. Doyle, W. Wierenga, and M.A. Zaleta J. Org. Chem. 37 1972 1597 1601
41. J.M. Tedder Tetrahedron 1 1957 270 271
42. B. Schmidt, R. Berger, and F. Hölter Org. Biomol. Chem. 8 2010 1406 1414
43. H.T. Clarke, and W.R. Kirner Org. Synth. 1 1941 374 376
44. J.L. Hartwell, and L.F. Fieser Org. Synth. 2 1943 145 147
45. D.Y. Curtin, and J.A. Ursprung J. Org. Chem. 21 1956 1221 1225
46. K. Hunger, P. Mischke, W. Rieper, R. Raue, K. Kunde, and A. Engel 'Azo Dyes' in Ullmann's Encyclopedia of Industrial Chemistry 2005 Wiley-VCH Weinheim
47. W.W. Hartman, and J.B. Dickey Org. Synth. 2 1943 163 165
48. O. Widman Ber. 17 1884 722 727
49. R. Stoermer, and H. Fincke Ber. 42 1909 3115 3132
50. T. Sandmeyer Ber. 17 1884 1633 1635
51. G. Balz, and G. Schiemann Ber. 60 1927 1186 1190
52. H. Meerwein, E. Buchner, and K. van Emsterk J. Prakt. Chem. 152 1939 237 266
53. R. Pschorr Ber. 29 1896 496 501
54. M. Gomberg, and W.E. Bachmann J. Am. Chem. Soc. 42 1924 2339 2343
55. R. Huisgen, and R. Lux Chem. Ber. 93 1960 540 544
56. K. Kikukawa, and T. Matsuda Chem. Lett. 1977 159 162
57. K. Kikukawa, K. Nagira, and T. Matsuda Bull. Chem. Soc. Jpn. 50 1977 2207
58. K. Kikukawa, K. Nagira, N. Terao, F. Wada, and T. Matsuda Bull. Chem. Soc. Jpn. 52 1979 2609 2610
59. C.S. Rondestveldt Jr. Org. React. 11 1960 189 260
60. K. Kikukawa, K. Nagira, F. Wada, and T. Matsuda Tetrahedron 37 1981 31 36
61. K. Kikukawa, K. Maemura, K. Nagira, F. Wada, and T. Matsuda Chem. Lett. 1980 551 552
62. K. Kikukawa, K. Maemura, Y. Kiseki, F. Wada, and T. Matsuda J. Org. Chem. 46 1981 4885 4888
63. A.A. Sabino, A.H.L. Machado, C.R.D. Correia, and M.N. Eberlin Angew. Chem., Int. Ed. 43 2004 2154 2158
64. F.-X. Felpin, K. Miqueu, J.-M. Sotiropoulos, E. Fouquet, O. Ibarguren, and J. Laudien Chem. - Eur. J. 16 2010 5191 5204
65. A. Pla-Quintana, and A. Roglans ARKIVOC ix 2005 51 62
66. S. Yasui, M. Fujii, C. Kawano, Y. Nishimura, and A. Ohno Tetrahedron Lett. 32 1991 5601 5604
67. M. Barbero, M. Crisma, I. Degani, R. Fochi, and P. Perracino Synthesis 1998 1171 1175
68. E. Artuso, M. Barbero, I. Degani, S. Dughera, and R. Fochi Tetrahedron 62 2006 3146 3157
69. S. Sengupta, S.K. Sadhukhan, and S. Bhattacharyya Tetrahedron 53 1997 2213 2218
70. W. Yong, P. Yi, Z. Zhuangyu, and H. Hongwen Synthesis 1991 967 969
71. S. Sengupta, S.K. Sadhukhan, S. Bhattacharyya, and J. Guha J. Chem. Soc., Perkin Trans. 1 1998 407 410
72. R. Perez, D. Veronese, F. Coelho, and O.A.C. Antunes Tetrahedron Lett. 47 2006 1325 1328
73. T. Konno, S. Yamada, A. Tani, T. Miyabe, and T. Ishihara Synlett 2006 3025 3028
74. T. Konno, S. Yamada, A. Tani, T. Miyabe, T. Ishihara, and M. Nishida J. Fluorine Chem. 130 2009 913 921
75. S. Sengupta, S.K. Sadhukhan, and S. Bhattacharyya J. Chem. Soc., Perkin Trans. 1 1998 275 277
76. S. Sengupta, S.K. Sadhukhan, and R.S. Singh Indian J. Chem. 40B 2001 997 999
77. S. Darses, M. Pucheault, and J.-P. Genêt Eur. J. Org. Chem. 2001 1121 1128
78. J. Cesar-Pastre, and C. Roque Duarte Correia Adv. Synth. Catal. 351 2009 1217 1223
79. S. Sengupta, and S. Bhattacharyya J. Chem. Soc., Perkin Trans. 1 1993 1943 1944
80. S. Sengupta, and S. Bhattacharyya Tetrahedron Lett. 36 1995 4475 4478
81. M. Barbero, S. Cadamuro, and S. Dughera Synthesis 2006 3443 3452
82. G. Bartoli, S. Cacchi, G. Fabrizi, and A. Goggiamani Synlett 2008 2508 2512
83. M.B. Andrus, C. Song, and J. Zhang Org. Lett. 4 2002 2079 2082
84. G.W. Kabalka, G. Dong, and B. Venkataiah Tetrahedron Lett. 45 2004 2775 2777
85. A.V. Moro, F.S. Cardoso, and C. Correia Tetrahedron Lett. 49 2008 5668 5671
86. H. Brunner, N. Le Cousturier de Courcy, and J.-P. Genêt Synlett 2000 201 204
87. K. Selvakumar, A. Zapf, A. Spannenberg, and M. Beller Chem. - Eur. J. 8 2002 3901 3906
88. M. Dai, B. Liang, C. Wang, J. Chen, and Z. Yang Org. Lett. 6 2004 221 224
89. J. Masllorens, M. Moreno-Mañas, A. Pla-Quintana, and A. Roglans Org. Lett. 5 2003 1559 1561
90. J. Masllorens, S. Bouquillon, A. Roglans, F. Hénin, and J. Muzart J. Organomet. Chem. 690 2005 3822 3826
91. M. Beller, and K. Kühlein Synlett 1995 441 442
92. T. Stern, S. Rückbrod, C. Czekelius, C. Donner, and H. Brunner Adv. Synth. Catal. 352 2010 1983 1992
93. F.-X. Felpin, E. Fouquet, and C. Zakri Adv. Synth. Catal. 350 2008 2559 2565
94. H. Brunner, N. Le Cousturier de Courcy, and J.-P. Genêt Tetrahedron Lett. 40 1999 4815 4818
95. F.-X. Felpin, and E. Fouquet Adv. Synth. Catal. 350 2008 863 868
96. S. Sengupta, and S.K. Sadhukhan Tetrahedron Lett. 39 1998 715 718
97. For selected references, see:
98. J.E. Aho, P.M. Pihko, and T.K. Rissa Chem. Rev. 105 2005 4406 4440
99. A.R. Gallimore, and J.B. Spencer Angew. Chem., Int. Ed. 45 2006 4406 4413
100. M. Brasholz, S. Sörgel, C. Azap, and H.-U. Reißig Eur. J. Org. Chem. 2007 3801 3814
101. For selected references, see:
102. M. Sefkow Synthesis 2003 2595 2625
103. M. Sasaki, and H. Fuwa Synlett 2004 1851 1874
104. I. Kadota, and Y. Yamamoto Acc. Chem. Res. 38 2005 423 432
105. M. Inoue Chem. Rev. 105 2005 4379 4405
106. R. Halim, and M.A. Brimble Org. Biomol. Chem. 4 2006 4048 4058
107. K.C. Nicolaou, M.O. Frederick, and R.J. Aversa Angew. Chem., Int. Ed. 47 2008 7182 7225
108. G. Mehta, and S. Sengupta Tetrahedron Lett. 37 1996 8625 8626
109. S. Cacchi, G. Fabrizi, A. Goggiamani, and A. Sferrazza Synlett 2009 973 977
110. A.H.L. Machado, M.A. de Sousa, D.C.S. Patto, L.F.S. Azevedo, F.I. Bombonato, and C.R.D. Correia Tetrahedron Lett. 50 2009 1222 1225
111. P.R.R. Meira, A.V. Moro, and C.R.D. Correia Synthesis 2007 2279 2286
112. A.C.B. Burtoloso, A.L.L. Garcia, K.C. Miranda, and C.R.D. Correia Synlett 2006 3145 3149
113. S. Cacchi, G. Fabrizi, A. Goggiamani, and A. Sferrazza Synlett 2009 1277 1280
114. F.A. Siqueira, J.G. Taylor, and C.R.D. Correia Tetrahedron Lett. 51 2010 2102 2105
115. E.D. Coy, L. Jovanovic, and M. Sefkow Org. Lett. 12 2010 1976 1979
116. B. Schmidt Chem. Commun. 2003 1656 1657
117. B. Schmidt, and F. Hölter Chem. - Eur. J. 15 2009 11948 11953
118. B. Schmidt, and A. Biernat Eur. J. Org. Chem. 2008 5764 5769
119. A.V. Moro, F.S.P. Cardoso, and C.R.D. Correia Org. Lett. 11 2009 3642 3645
120. L.-H. Xu, Y.-Y. Zhang, X.-L. Wang, and J.-Y. Chou Dyes Pigm. 62 2004 283 289
121. For selected references, see:
122. I. Moldvai, E. Temesvári-Major, M. Incze, G. Dörnyei, E. Szentirmay, and C. Szántay Helv. Chim. Acta 88 2005 1344 1356
123. F.-X. Felpin, and J. Lebreton Tetrahedron 60 2004 10127 10153
124. N.K. Garg, and B.M. Stoltz Chem. Commun. 2006 3769 3779
125. B.M. Trost, and M.K. Brennan Synthesis 2009 3003 3025
126. For selected references, see:
127. D.J. Newman, and G.M. Cragg J. Nat. Prod. 67 2004 1216 1238
128. R.M. Wilson, and S.J. Danishefsky J. Org. Chem. 71 2006 8329 8351
129. D.J. Newman, and G.M. Cragg J. Nat. Prod. 70 2007 461 477
130. For selected references, see:
131. F.-X. Felpin, and J. Lebreton Eur. J. Org. Chem. 2003 3693 3712
132. F.-X. Felpin, and J. Lebreton Curr. Org. Synth. 1 2004 83 109
133. M.G.P. Buffat Tetrahedron 60 2004 1701 1729
134. J. Royer, M. Bonin, and L. Micouin Chem. Rev. 104 2004 2311 2352
135. M. Zhang Adv. Synth. Catal. 351 2009 2243 2270
136. C. Sonesson, and A. Hallberg Tetrahedron Lett. 36 1995 4505 4506
137. M.J.S. Carpes, and C.R.D. Correia Synlett 2000 1037 1039
138. R.L. Barreto, L.B.L.R. Nacimbem, and C.R.D. Correia Synth. Commun. 37 2007 2011 2018
139. R.L. Barreto, M.J.S. Carpes, C.C. Santana, and C.R.D. Correia Tetrahedron: Asymmetry 18 2007 435 442
140. A.C.B. Monte de Oca, and C.R.D. Correia ARKIVOC 10 2003 390 403
141. A.L.L. Garcia, M.J.S. Carpes, A.C.B.M. De Oca, M.A.G. dos Santos, C.C. Santana, and C.R.D. Correia J. Org. Chem. 70 2005 1050 1053
142. M.J.S. Carpes, and C.R.D. Correia Tetrahedron Lett. 43 2002 741 744
143. K. Peixoto da Silva, M.N. Godoi, and C.R.D. Correia Org. Lett. 9 2007 2815 2818
144. J. Ezquerra, A. Escribano, A. Rubio, M.J. Remuiñán, and J.J. Vaquero Tetrahedron: Asymmetry 7 1996 2613 2626
145. J. Ezquerra, A. Escribano, A. Rubio, M.J. Remuiñán, and J.J. Vaquero Tetrahedron Lett. 36 1995 6149 6152
146. A. Lázaro, L. Garcia, and C.R.D. Correia Tetrahedron Lett. 44 2003 1553 1557
147. D.F. Oliveira, E.A. Saverino, and C.R.D. Correia Tetrahedron Lett. 40 1999 2083 2086
148. E.A. Saverino, and C.R.D. Correia Org. Lett. 2 2000 3039 3042
149. E.A. Saverino, E.R. Costenaro, A.L.L. Garcia, and C.R.D. Correia Org. Lett. 5 2003 305 308
150. F.-X. Felpin, O. Ibarguren, L. Nassar-Hardy, and E. Fouquet J. Org. Chem. 74 2009 1349 1352
151. O. Ibarguren, C. Zakri, E. Fouquet, and F.-X. Felpin Tetrahedron Lett. 50 2009 5071 5074
152. J.C. Pastre, and C.R.D. Correia Org. Lett. 8 2006 1657 1660
153. J.C. Pastre, Y. Génisson, N. Saffon, J. Dandurand, and C.R.D. Correia J. Braz. Chem. Soc. 21 2010 821 836
154. F.-X. Felpin, J. Coste, C. Zakri, and E. Fouquet Chem. - Eur. J. 15 2009 7238 7245
155. J. Laudien, E. Fouquet, C. Zakri, and F.-X. Felpin Synlett 2010 1539 1543
156. F.-X. Felpin, E. Fouquet, and C. Zakri Adv. Synth. Catal. 351 2009 649 655
157. B. Schmidt, F. Hölter, R. Berger, and S. Jessel Adv. Synth. Catal. 352 2010 2463 2473