Pyrazole-tethered phosphine ligands for Pd(0): Useful catalysts for Stille, Kumadaand Hiyama cross-coupling reactions

Tetrahedron

Volumn 66, Issue 29, 2010, Pages 5451-5458

  Pal, Anwesha ^a   Ghosh, Raju ^a   Adarsh, N N ^a   Sarkar, Amitabha ^a  

^a DEPARTMENT OF MATERIALS SCIENCE   (India)

Author keywords

Cross couplingreaction; Palladium complex; Pyrazolyl based phosphine ligands; Stille, Kumada, Hiyama

Indexed keywords

3 TERT BUTYL 5 METHYL 1 [2 (DIPHENYLPHOSPHINO)PHENYL] 1H PYRAZOLE; 3,5 DIMETHYL 1 [2 (DIPHENYLPHOSPHINO)PHENYL] 1H PYRAZOLE; PALLADIUM; PHOSPHINE; PYRAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; HIYAMA REACTION; KUMADA REACTION; PRIORITY JOURNAL; STILLE REACTION; X RAY DIFFRACTION;

EID: 77954314464     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.05.026     Document Type: Article

References (133)

1. (a)Alberico, D.; Scott, M.E.; Lautens, M.Chem.Rev.2007, 107, 174;
2. (b)Corbet, J.-P.; Mignani, G.Chem.Rev.2006, 106, 2651;
3. (c)Cross-Coupling Reactions: A Practical Guide in Topics in Current Chemistry; Houk, K.N., Sessler, H., Lehn, J.-M., Ley, S.V., de Meijere, A., Schreiber, S.L., Thiem, J., Trost, B.M., Vo€gtle, F., Yamamoto, H., Eds.; Springer: Heidelberg, 2002; Vol.219;
4. (d)Hegedus, L.S.In Organometallics in Organic Synthesis; Schlosser, M., Ed.; Wiley: New York, NY, 1994; p 383;
5. (e)Palladium Reagents and Catalysts: Innovations in Organic Synthesis; Fuji, J., Ed.; Wiley: Chichester, UK, 1995;
6. (f)Geissler, H.In Transition Metals for Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, 1998; Vol.1, pp 158-193;
7. (g)Metal-Catalyzed Cross-coupling Reactions; Diederich, F., Stang, P.J., Eds.; Wiley-VCH: Weinheim, Germany, 1998
8. (h)Palladium in Heterocyclic Chemistry: A Guide for the Synthetic Chemist; Li, J.J., Gribble, G.W., Eds.; Pergamon: Amsterdam, 2000.
9. (a)Yin, L.; Liebscher, J.Chem.Rev.2007, 107, 133;
10. (b)Phan, N.T.S.; Van Der Sluys, M.; Jones, C.W.Adv.Synth.Catal.2006, 348, 609;
11. (c)Hassan, J.; Sévignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M.Chem.Rev.2002, 102, 1359;
12. (d)Belardi, J.K.; Micalizio, G.C.Angew.Chem., Int.Ed.2008, 47, 4005;
13. (e)Jia, Y.; Bois-Choussy, M.; Zhu, J.Angew.Chem., Int.Ed.2008, 47, 4167;
14. (f)Burlison, J.A.; Neckers, L.; Smith, A.B.; Maxwell, A.; Blagg, B.S.J.J.Am.Chem.Soc.2006, 128, 15529;
15. (g)Nicolaou, K.C.; Li, H.; Boddy, C.N.C.; Ramanjulu, J.M.; Yue, T.Y.; Natarajan, S.; Chu, X.; Bra€se, J.S.; Rübsam, F.Chem.dEur.J.1999, 5, 2584
16. (h)Stanforth, S.P.Tetrahedron 1998, 54, 263.
17. (a)Tamao, K.; Sumitani, K.; Kumada, M.J.Am.Chem.Soc.1972, 94, 4374;
18. (b)Phan, N.T.S.; Brown, D.H.; Styring, P.Green Chem.2004, 6, 526.
19. (a)Negishi, E.Acc.Chem.Res.1982, 15, 340;
20. (b)Negishi, E.; Anastasia, L.Chem.Rev.2003, 103, 1979.
21. (a)Milstein, D.; Stille, J.K.J.Am.Chem.Soc.1978, 100, 3636
22. (b)Stille, J.K.Angew.Chem., Int.Ed.Engl.1986, 25, 508;
23. (c)Garcia-Martinez, J.C.; Lezutekong, R.; Crooks, R.M.J.Am.Chem.Soc.2005, 127, 5097.
24. (a)Miyaura, N.; Suzuki, A.Chem.Rev.1995, 95, 2457;
25. (b)Suzuki, A.J.Organomet.Chem.1999, 576, 147;
26. (c)Wolfe, J.P.; Singer, R.A.; Yang, B.H.; Buchwald, S.L.J.Am.Chem.Soc. 1999, 121, 9550;
27. (d)Littke, A.F.; Dai, C.; Fu, G.C.J.Am.Chem.Soc.2000, 122, 4020;
28. (e)Kotha, S.; Lahiri, K.; Kashinath, D.Tetrahedron 2002, 58, 9633;
29. (f)Navarro, O.; Oonishi, Y.; Kelly, R.A.; Stevens, E.E.; Briel, O.; Nolan, S.P.J.Organomet.Chem.2004, 689, 3722;
30. (g)Mukherjee, A.; Sarkar, A.Tetrahedron Lett.2005, 46, 15;
31. (h)Srimani, D.; Sarkar, A.Tetrahedron Lett.2008, 49, 6304;
32. (i)Patil, S.A.; Weng, C.-M.; Huang, P.-C.; Hong, F.-E.Tetrahedron 2009, 65, 2889.
33. (a)Sonogashira, K.; Tohda, Y.; Hagihara, N.Tetrahedron Lett.1975, 16, 4467;
34. (b)Sonogashira, K.J.Organomet.Chem.2002, 653, 46;
35. (c)Beletskaya, I.P.; Cheprakov, A.V.Chem.Rev.2000, 100, 3066.
36. (a)For a review of the Hiyama reaction, see: Hiyama, T.In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P.J., Eds.; Wiley-VCH: New York, NY, 1998; Chapter 10;
37. (b)Hiyama, T.J.Organomet.Chem.2002, 653, 58;
38. (c)Denmark, S.E.; Baird, J.D.Chem.dEur.J.2006, 12, 4954
39. (d)Strotman, N.A.; Sommer, S.; Fu, G.C.Angew.Chem., Int.Ed.2007, 46, 3556.
40. (a)Guram, A.S.; Rennels, R.A.; Buchwald, S.L.Angew.Chem., Int.Ed.1995, 34, 1348;
41. (b)Louie, J.; Hartwig, J.F.Tetrahedron Lett.1995, 36, 3609;
42. (c)Wolfe, J.P.; Wagaw, S.; Buchwald, S.L.J.Am.Chem.Soc.1996, 118, 7215;
43. (d)Driver, M.S.; Hartwig, J.F.J.Am.Chem.Soc.1996, 118, 7217;
44. (e)Driver, M.S.; Hartwig, J.F.J.Am.Chem.Soc.1997, 119, 8232;
45. (f)Hamann, B.C.; Hartwig, J.F.J.Am.Chem.Soc.1998, 120, 7369;
46. (g)Hartwig, J.F.; Kawatsura, M.; Hauck, S.I.; Shaughnessy, K.H.; Alcazar-Roman, L.M.J.Org.Chem.1999, 64, 5575
47. (h)Wolfe, J.P.; Buchwald, S.L.Angew.Chem., Int.Ed.1999, 38, 2413;
48. (i)Yin, J.; Buchwald, S.L.J.Am.Chem.Soc.2002, 124, 6043;
49. (j)Schlummer, B.; Scholz, U.Synth.Catal.2004, 346, 1599.
50. (a) Palucki M.; Buchwald S.L.J.Am.Chem.Soc.1997, 119, 11108;
51. (b)Hamann, B.C.; Hartwig, J.F.J.Am.Chem.Soc.1997, 119, 12382;
52. (c)Kawatsura, M.; Hartwig, J.F.J.Am.Chem.Soc.1999, 121, 1473;
53. (d)Lee, S.; Hartwig, J.F.J.Org.Chem.2001, 66, 3402;
54. (e)Lee, S.; Beare, N.A.; Hartwig, J.F.J.Am.Chem.Soc.2001, 123, 8410;
55. (f)Jo€rgensen, M.; Lee, S.; Liu, X.; Wolkowski, J.P.; Hartwig, J.F.J.Am.Chem.Soc.2002, 124, 12557;
56. (g)Beare, N.A.; Hartwig, J.F.J.Org.Chem.2002, 67, 541;
57. (h)Culkin, D.A.; Hartwig, J.F.Acc.Chem.Res.2003, 36, 234;
58. (i)Hama, T.; Culkin, D.A.; Hartwig, J.F.J.Am.Chem.Soc.2006, 128, 4976.
59. (a)Littke, A.F.; Fu, G.C.Angew.Chem., Int.Ed.2002, 41, 4176;
60. (b)Bedford, R.B.Chem.Commun.2003, 1787
61. (c)Miura, M.Angew.Chem., Int.Ed.2004, 43, 2201;
62. (d)Botella, L.; Nàjera, C.Angew.Chem., Int.Ed.2002, 41, 179;
63. (e)Colacot, T.J.; Shea, H.A.Org.Lett.2004, 6, 3731
64. (f)Bohm, V.P.; Weskamp, W.T.; Gsto€ttmayer, C.W.K.; Herrmann, W.A.Angew.Chem., Int.Ed.2000, 39, 1602;
65. (g)Nabera, J.R.; Buchwald, S.L.Adv.Synth.Catal.2008, 350, 957 and references cited therein;
66. (h)Yu, S.-B.; Hua, X.-P.; Huang, J.-D.; Wang, D.-Y.; Duan, Z.-C.; Zheng, Z.Tetrahedron Lett.2008, 49, 1253 and references cited therein;
67. (i)Gouda, K.-I.; Hagiwara, E.; Hatanaka, Y.; Hiyama, T.J.Org.Chem.1996, 61, 7232.
68. (a)Mukherjee, A.; Sarkar, A.Tetrahedron Lett.2004, 45, 9525;
69. (b)Mukherjee, A.; Sarkar, A.Arkivo 2003, 87.
70. (a)Nicolaou, K.C.; Li, Y.; Sugita, K.; Monenschein, H.; Guntupali, P.; Mitchell, H.J.; Fylaktakidou, K.C.; Vourloumis, D.; Giannakakou, P.; O'Brate, A.J.Am.Chem.Soc.2003, 125, 15443;
71. (b)Kadota, I.; Takamura, H.; Sato, K.; Ohno, A.; Matsuda, K.; Yamamoto, Y.J.Am.Chem.Soc.2003, 125, 46;
72. (c)Lin, S.-Y.; Chen, C.-L.; Lee, Y.-J.J.Org.Chem.2003, 68, 2968;
73. (d)Boger, D.L.; Ichikawa, S.; Jing, H.J.Am.Chem.Soc.2000, 122, 12169;
74. (e)Jensen, M.S.; Yang, C.; Hsiao, Y.; Rivera, N.; Wells, K.M.; Chung, J.Y.L.; Yasuda, N.; Hughes, D.L.; Reider, P.J.Org.Lett.2000, 2, 1081.
75. Kuribayashi, T.; Gohya, S.; Mizuno, Y.; Satoh, S.J.Carbohyd.Chem.1999, 18, 383
76. Nicolaou, K.C.; King, N.P.; Finlay, M.R.V.; He, Y.; Roschangar, F.; Vourloumis, D.; Vallberg, H.; Sarabia, F.; Ninkovic, S.; Hepworth, D.Bioorg.Med.Chem.1999, 7, 665.
77. See Ref.1g;
78. (b)Shirakawa, E.; Hiyama, T.J.Organomet.Chem.1999, 576, 169;
79. (c)Miyaura, N.Cross-Coupling Reaction; Springer: Berlin, 2002;
80. (d)Hegedus, L.S.In Oranometallics in Synthesis; Schlosser, M., Ed.; J.Wiley & Sons: Chichester, UK, 2002; p 1123;
81. (e)Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-Interscience: New York, NY, 2002;
82. (f)Espinet, P.; Echavarren, A.M.Angew.Chem., Int.Ed.2004, 43, 4704.
83. (a) Litter, A.F.; Fu, G.C.Angew.Chem., Int.Ed.1999, 38, 2411;
84. (b)Grasa, G.A.; Nolan, S.P.Org.Lett.2001, 3, 119;
85. (c)Litter, A.F.; Schwarz, L.; Fu, G.C.J.Am.Chem.Soc.124, 6343 and references cited therein;
86. (d)Kim, Y.M.; Yu, S.J.Am.Chem.Soc.2003, 125,1696;
87. (e)Menzel, K.; Fu, G.C.J.Am.Chem.Soc.2003, 125, 3718;
88. (f)Kim, W.-S.; Kim, H.-J.; Cho, C.-G.J.Am.Chem.Soc.2003, 125, 14288;
89. (g)Dubbaka, S.R.; Vogel, P.J.Am.Chem.Soc.2003, 125, 15292
90. (h)Tang, H.; Menzel, K.; Fu, G.C.Angew.Chem., Int.Ed.2003, 42, 5079;
91. (i)Wolf, C.; Lerebours, R.J.Org.Chem.68, 7077;
92. (j)Wolf, C.; Lerebours, R.J.Org.Chem.2003, 68, 7551
93. (k)Mee, S.P.H.; Lee, V.; Baldwin, J.E.Angew.Chem., Int.Ed.2004, 43, 1132;
94. (l)Su, W.; Urgaonkar, S.; Verkade, J.G.Org.Lett.2004, 6, 1421;
95. (m)Mazzola, R.D., Jr.; Giese, S.; Benson, C.; West, F.G.J.Org.Chem.2004, 69, 220;
96. (n)Ho€genauer, K.Synlett 2001, 878;
97. (o)Scrivanti, A.; Matteoli, U.; Beghetto, V.; Antonaroli, S.; Crociani, B.Tetrahedron 2002, 58, 6881;
98. (p)Kim, N.; Kwon, M.S.; Park, C.M.; Park, J.Tetrahedron Lett.2004, 45, 7057.
99. (a)Goldman, E.R.; Medintz, I.L.; Whitley, J.L.; Hayhurst, A.; Clapp, A.R.; Uyeda, H.T.; Deschamps, J.R.; Lassman, M.E.; Mattoussi, H.J.Am.Chem.Soc.2005, 127, 6744;
100. (b)Braga, A.A.C.; Morgon, N.H.; Ujaque, G.; Maseras, F.J.Am.Chem.Soc. 2005, 127, 9298.
101. (a)Miyaura, N.; Yamada, K.; Suginome, H.; Suzuki, A.J.Am.Chem.Soc.1985, 107, 972;
102. (b)Grasa, G.A.; Hillier, A.C.; Nolan, S.P.Org.Lett.2001, 3, 1077;
103. (c)Dubbaka, S.R.; Vogel, P.Org.Lett.2004, 6, 95
104. (a)See Ref.1g;
105. (b)Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany, 2004; Vols.1 and 2;
106. (c)Corriu, R.J.P.; Masse, J.P.J.Chem.Soc., Chem.Commun.1972, 144;
107. (d)Schro€ter, S.; Stock, C.; Bach, T.Tetrahedron 2005, 61, 2245.
108. (a) Denmark S.E.; Sweis R.F.Acc.Chem.Res.2002, 35, 835;
109. (b)Itami, K.; Nokami, T.; Yoshida, J.-I.J.Am.Chem.Soc.2001, 123, 5600 and references therein;;
110. (c)Lee, J.-Y.; Fu, G.C.J.Am.Chem.Soc.2003, 125, 5616;
111. (d)Clarke, M.L.Adv.Synth.Catal.2005, 347, 303;
112. (e)Seganish, W.M.; Handy, C.J.; DeShong, P.J.Org.Chem.2005, 70, 8948;
113. (f)Alacid, E.; Nàjera, C.Adv.Synth.Catal.2006, 348, 945;
114. (g)Denmark, S.E.; Butler, C.R.Org.Lett.2006, 8, 63;
115. (h)Gordillo, À.; de Jesús, E.; López-Mardomingo, C.Org.Lett.2006, 8, 3517;
116. (i)Napier, S.; Marcuccio, S.M.; Tye, H.; Whittaker, M.Tetrahedron Lett.2008, 49, 3939;
117. (j)Napier, S.; Marcuccio, S.M.; Tye, H.; Whittaker, M.Tetrahedron Lett.2008, 49, 6314;
118. (k)Nakao, Y.; Oda, T.; Sahoo, A.K.; Hiyama, T.J.Organomet.Chem.2003, 687, 570;
119. (l)Sahoo, A.K.; Oda, T.; Nakao, Y.; Hiyama, T.Adv.Synth.Catal.2004, 346, 1715;
120. (m)Shibata, K.; Miyazawa, K.; Goto, Y.Chem.Commun.1997, 1309;
121. (n)Hirabayashi, K.; Mori, A.; Kawashima, J.; Suguro, M.; Nishihara, Y.; Hiyama, T.J.Org.Chem.2000, 65, 5342;
122. (o)Riggleman, S.; DeShong, P.J.Org.Chem.2003, 68, 8106;
123. (p)Mowery, M.E.; DeShong, P.J.Org.Chem.1999, 64, 1684;
124. (q)Lee, H.M.; Nolan, S.P.Org.Lett.2000, 2, 2053;
125. (r)Denmark, S.E.; Ober, M.H.Org.Lett.2003, 5, 1357;
126. (s)Mowery, M.E.; DeShong, P.Org.Lett.1999, 1, 2137;
127. (t)Seganish, W.M.; De-Shong, P.J.Org.Chem.2004, 69, 1137;
128. (u)Nakao, Y.; Imanaka, H.; Sahoo, A.K.; Yada, A.; Hiyama, T.J.Am.Chem.Soc.2005, 127, 6952;
129. (v)Wolf, C.; Lerebours, R.; Tanzini, E.H.Synthesis 2003, 2069;
130. (w)Koike, T.; Mori, A.Synlett 2003, 1850.
131. Hatanaka, Y.; Hiyama, T.J.Org.Chem.1988, 53, 918.
132. Grossman, O.; Azerraf, C.; Gelman, D.Organometallics 2006, 25, 375.
133. Bianchini, C.; Gatteschi, D.; Giambastiani, G.; Rios, I.G.; Ienco, A.; Laschi, F.; Mealli, C.; Meli, A.; Sorace, L.; Toti, A.; Vizza, F.Organometallics 2007, 26, 726.