Potassium organotrifluoroborates: New perspectives in organic synthesis

Chemical Reviews

Volumn 108, Issue 1, 2008, Pages 288-325

  Darses, Sylvain ^a   Genet, Jean Pierre ^a  

^a PSL RESEARCH UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANIC SYNTHESIS; POLAR SOLVENTS; POTASSIUM ORGANOTRIFLUOROBORATES;

DERIVATIVES; MOISTURE; NUCLEAR MAGNETIC RESONANCE; PURIFICATION; SOLVENTS; SYNTHESIS (CHEMICAL);

POTASSIUM COMPOUNDS;

BORIC ACID; FLUOROBORIC ACID; HEAVY METAL; ORGANIC COMPOUND; POTASSIUM DERIVATIVE; UNCLASSIFIED DRUG;

CATALYSIS; CHEMISTRY; REVIEW; SYNTHESIS;

BORATES; CATALYSIS; METALS, HEAVY; ORGANIC CHEMICALS; POTASSIUM COMPOUNDS;

EID: 38749104743     PISSN: 00092665     EISSN: None     Source Type: Journal    
DOI: 10.1021/cr0509758     Document Type: Review

References (375)

1. Omae, I. Applications of Organometallic Compounds; John Wiley and Sons: Chichester, 1998.
2. Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998.
3. For reviews concerning Miyaura-Suzuki cross-coupling reactions, see: (a) Kotha, S.; Lahiri, K.; Kashinath, D. Tetrahedron 2002, 58, 9633.
4. (b) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
5. Reviews on organoboron compounds synthesis: (a) Pelter, A.; Smith, K.; Brown, H. C. Borane Reagents; Academic Press: London, 1988.
6. (b) Matteson, D. S. Reactivity and Structure Concept in Organic Synthesis: Stereodirected Synthesis with Organoboranes; Springer: New York, 1994; Vol. 32.
7. (c) Vaultier, M.; Carboni, B. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon: New York, 1995; Vol. 11, p 191.
8. (d) Smith, K.; Pelter, A. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 8, p 703.
9. Davies, A. G.; Roberts, B. P. Chem Commun. 1966, 298.
10. Darses, S.; Genet, J.-P. Eur. J. Org. Chem. 2003, 4313.
11. (a) Molander, G. A.; Figueroa, R. Aldrichim. Acta 2005, 38,49.
12. (b) Molander, G. A.; Ellis, N. Acc. Chem. Res. 2007, 40, 275.
13. Stefani, H. A.; Cella, R.; Vieira, A. S. Tetrahedron 2007, 63, 3623.
14. For recent examples: (a) Ue, M.; Fujii, T.; Zhou, Z.-B.; Takeda, M.; Kinoshita, S. Solid State Ionics 2006, 177, 323.
15. (b) Zhou, Z.-B.; Matsumoto, H.; Tatsumi, K. Chem. Eur. J. 2006, 12, 2196.
16. For some patented applications: (a) Fukui, T. (Canon K. K., Japan) JP Patent 02003052, 1990.
17. (b) Takeda, M.; Takehara, M.; Ue, M. (Mitsubishi Chemical Corp., Japan) JP Patent 2002063934, 2002.
18. (c) Kawasato, T.; Hiratsuka, K.; Yoshida, N.; Ikeda, K. (Asahi Glass Co., Ltd, Japan) JP Patent 2003188053, 2003.
19. (d) Gambut, L.; Vergelati, C.; Sanchez, J.-Y.; Alloin, F. (Rhodia Chimie, France) WO Patent 2004091033, 2004.
20. (e) Nagakura, N. (Tokuyama Corp., Japan) JP Patent 2004175667, 2004.
21. (f) Ignatyev, N.; Welz-Biermann, U.; Bissky, G.; Willner, H.; Kucheryna, A. (Merck GmbH, Germany) WO Patent 2005105815, 2005.
22. (g) Matsui, T.; Deguchi, M.; Yoshzawa, H. (Matsushita Electric Industrial Co., Ltd., Japan) WO Patent 2006095507, 2006.
23. (h) Siggel, A.; Theissen, M.; Kanschik-Conradsen, A.; Dernel, S.; Nerenz, F. (Honeywell International Inc., U.S.A.) WO Patent 2006096578, 2006.
24. (i) Yoshida, H.; Yuyama, K.; Masuda, A. (Nisshin Spinning Co., Ltd., Japan) JP Patent 2006236829, 2006.
25. (j) Yamaguchi, H.; Kawashima, A.; Kubota, T. (Sony Corp., Japan) JP Patent 2006261092, 2006.
26. (k) Kishi, T.; Kuboki, T.; Saruwatari, H.; Takami, N. (Kabushiki Kaisha Toshiba, Japan) U.S. Patent 2006068282, 2006.
27. (I) Nishida, T.; Hirano, K.; Tomisaki, M.; Tashiro, Y.; Tsummaru, H.; Nabeshima, A.; Abe, Y.; Tokuda, H.; Oka, A. (Otsuka Chemical Co., Ltd., Japan; Stella Chemifa Corp.) WO Patent 2006077894, 2006.
28. For recent examples: (a) Zhao, D.; Fei, Z.; Ohlin, A.; Laurenczy, G.; Dyson, P. J. Chem. Commun. 2004, 2500.
29. (b) Zhou, Z.-B.; Matsumoto, H.; Tatsumi, K. Chem. Eur. J. 2004, 10, 6581.
30. (c) Zhou, Z.-B.; Matsumoto, H.; Tatsumi, K.; Chem. Lett. 2004, 33, 1636.
31. (d) Zhou, Z.-B.; Matsumoto, H.; Tatsumi, K. Chem. Eur. J. 2005, 11, 752.
32. (e) Zhou, Z.-B.; Matsumoto, H.; Tatsumi, K. ChemPhysChem 2005, 6, 1324.
33. For some patented applications: (a) Welz-Biermann, U.; Ignatyev, N.; Willner, H.; Bissky, G. (Merck GmbH, Germany) WO Patent 2004106288, 2004.
34. (b) Dyson, P.; Zhao, D.; Fei, Z. (Ecole Polytechnique Fédérale de Lausane Epfl, Switzerland) WO Patent 2005019185, 2005.
35. (c) Haneyama, M.; Moriuchi, T. (Kyodo Yushi Co., Ltd., Japan) JP Patent 2005154755, 2005.
36. (d) Matsumoto, H.; Zhou, Z.-B. (National Institute of Advanced Industrial Science and Technology, Japan) WO Patent 2005063773, 2005.
37. (e) Matsumoto, H.; Zhou, Z.-B. (National Institute of Advanced Industrial Science and Technology, Japan) WO Patent 2006070545, 2006.
38. Fowler, D. L.; Kraus, C. A. J. Am. Chem. Soc. 1940, 62, 1143.
39. Brauer, D. J.; Bürger, H.; Pawelke, G. Inorg. Chem. 1977, 16, 2305.
40. (a) Chambers, R. D.; Clark, H. C.; Willis, C. J. Prod. Chem. Soc. 1960, 114.
41. (b) Chambers, R. D.; Clark, H. C.; Willis, C. J. J. Am. Chem. Soc. 1960, 82, 5298.
42. (a) Clark, H. C.; Willis, C. J. J. Am. Chem Soc. 1960, 82, 1888.
43. (b) Chambers, R. D.; Clark, H. C.; Willis, C. J. Chem. Ind. (London) 1960, 76.
44. Brauer, D. J.; Bürger, H.; Pawelke, G. J. Organomet. Chem. 1980, 192, 305.
45. Pawelke, G.; Heyder, F.; Bürger, H. J. Organomet. Chem. 1979, 178, 1.
46. Brauer, D. J.; Bürger, H.; Pawelke, G. J. Organomet. Chem. 1982, 238, 267.
47. (a) Stafford, S. L. Can. J. Chem. 1963, 41, 807-808.
48. (b) Stafford, S. L.; Township, M.; County, M. (Allied Chemical Corp.) GB Patent 973636, 1964.
49. Chivers, T. Can. J. Chem. 1970, 48, 3856.
50. Chambers, R. D.; Chivers, T.; Pyke, D. A. J. Chem. Soc. 1965, 5144.
51. Bir, G.; Schacht, W.; Kaufmann, D. J. Organomet. Chem. 1988, 340, 267.
52. Molander, G. A.; Cooper, D. J. Encyclopedia of Reagents for Organic Synthesis; John Wiley & Sons: New York, 2006; DOI 10.1002/ 047084289X.m00628.
53. Vedejs, E.; Chapman, R. W.; Fields, S. C.; Lin, S.; Schrimpf, M. R. J. Org. Chem. 1995, 60, 3020.
54. Thierig, D.; Umland, F. Naturwissenschaften 1967, 54, 563.
55. Vedejs, E.; Fields, S. C.; Hayashi, R.; Hitchcock, S. R.; Powell, D. R.; Schrimpf, M. R. J. Am. Chem. Soc. 1999, 121, 2460.
56. Darses, S.; Michaud, G.; Genet, J.-P. Eur. J. Org. Chem. 1999, 1875.
57. Unpublished results from our laboratory.
58. Molander, G. A.; Biolatto, B. Org. Lett. 2002, 4, 1867.
59. Molander, G. A.; Biolatto, B. J. Org. Chem. 2003, 68, 4302.
60. Frohn, H.-J.; Franke, H.; Fritzen, P.; Bardin, V. V. J. Organomet. Chem. 2000, 598, 127.
61. (a) Snieckus, V. Chem. Rev. 1990, 90, 879-933.
62. (b) Alessi, M.; Larkin, A. L.; Ogilvie, K. A.; Green, L. A.; Lai, S.; Lopez, S.; Snieckus, V. J. Org. Chem. 2007, 72, 1588 and references cited.
63. (a) Abo-Amer, N. Y.; Adonin, V. V.; Bardin, P.; Fritzen, H.-J.; Frohn, C.; Steinberg, J. Fluorine Chem. 2004, 125, 1771.
64. (b) Hecht, H.; Mueller, L.; Brehm, O.; Frohn, H.-J.; Fritzen, P. (Robert Bosch GmbH, Germany) DE Patent 10256255, 2004.
65. (a) Henderson, L. D.; Piers, W. E.; Chase, P. A. (University Technologies International, Inc., Can.) CA Patent 2463045, 2005.
66. (b) Chase, P. A.; Henderson, L. D.; Piers, W. E.; Parvez, M.; Clegg, W.; Elsegood, M. R. J. Organometallics 2006, 25, 349.
67. (c) Piers, W. E.; Chase, P. A.; Henderson, L. D. (University Technologies International Inc. Can.) U.S. Patent 2005222463, 2005.
68. Kennedy, J. P.; Collins, S.; Lewis, S. T. (The University of Akron, U.S.A.) WO Patent 2004094486, 2004.
69. (a) Molander, G. A.; Ito, T. I. Org. Lett. 2001, 3, 393.
70. (b) Molander, G. A.; Yun, C.-S.; Ribagorda, M.; Biolatto, B. J. Org. Chem. 2003, 68, 5534.
71. (c) Molander, G. A.; Ham, J.; Seapy, D. G. Tetrahedron 2007, 63, 768.
72. Matteson, D. S.; Kim, G. Y. Org. Lett. 2002, 4, 2153.
73. For example, see: (a) Ishiyama, T.; Murata, M.; Miyaura, N. J. Org. Chem. 1995, 60, 7508.
74. (b) Ishiyama, T.; Itoh, Y.; Kitano, T.; Miyaura, N. Tetrahedron Lett. 1997, 38, 3447.
75. (c) Murata, M.; Watanabe, S.; Masuda, Y. J. Org. Chem. 1997, 62, 6458.
76. (d) Murata, M.; Oyama, T.; Watanabe, S.; Masuda, Y. J. Org. Chem. 2000, 65, 164.
77. (e) Baudoin, O.; Guénard, D.; Guéritte, F. J. Org. Chem. 2000, 65, 9268.
78. Li, W.; Nelson, D. P.; Jensen, M. S.; Hoerrner, R. S.; Cai, D.; Larsen, R. D.; Reider, P. J. J. Org. Chem. 2002, 67, 5394.
79. Wilk, B. K.; Rubezhov, A. Z.; Helom, J.-L. (Wyeth) WO Patent 2005105817, 2005.
80. (a) Coghlan, S. W.; Giles, R. L.;. Howard, J. A. K; Patrick, L. G. F.; Probert, M. R.; Smith, G. E.; Whiting, A. J. Organomet. Chem. 2005, 690, 4784.
81. (b) Whiting, A. (University of Durham, U.K.) WO Patent 2004113351, 2004.
82. Giles, R. L.; Howard, J. A. K.; Patrick, L. G. F.; Probert, M. R.; Smith, G. E.; Whiting, A. J. Organomet. Chem. 2003, 680, 257.
83. Darses, S.; Michaud, G.; Genet, J.-P. Tetrahedron Lett. 1998, 39, 5045.
84. Molander, G. A.; Rivero, M. R. Org. Lett. 2002, 4, 107.
85. (a) De, S.; Welker, M. E. Org. Lett. 2005, 7, 2481.
86. (b) De, S.; Day, C.; Welker, M. E. Tetrahedron, doi: 10.1016/ j.tet.2007.08.063.
87. Chessari, G.; Congreve, M. S.; Figureroa Navarro, E.; Frederickson, M.; Murray, C.; Woolford, A. J.-A.; Carr, M. G.; O'Brien, M. A.; Woodhead, A. J. (Astex Therapeutics Limited, U.K.) WO Patent 2006109075,2006.
88. Matteson, D. S. J. Am. Chem. Soc. 1960, 82, 4228.
89. Bardin, V. V.; Frohn, H.-J. Z. Anorg. Allg. Chem. 2002, 628, 721.
90. Frohn, H.-J.; Adonin, N. Y.; Bardin, V. V. Z. Anorg. Allg. Chem. 2003, 629, 2499.
91. Frohn, H.-J.; Bardin, V. V. Z. Anorg. Allg. Chem. 2003, 629, 2465.
92. Frohn, H.-J.; Bardin, V. V. J. Fluorine Chem. 2003, 123, 43.
93. Adonin, N. Y.; Bardin, V. V.; Frohn, H.-J. Organometallics 2004, 23, 535.
94. Molander, G. A.; Katona, B. W.; Machrouki, F. J. Org. Chem. 2002, 67, 8416.
95. Yamamoto, Y.; Hattori, K.; Ishii, J.-I.; Nishiyama, H. Tetrahedron 2006, 62, 4294.
96. Bardin, V. V.; Adonin, N. Y.; Frohn, H.-J. Organometallics 2005, 24, 5311.
97. (a) Review: Negishi, E. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon: New York, 1983; Vol. 7, p 337. Lithium alkynyl(triisopropoxy)-borates have been shown to be stable at 0 °C for several months in the absence of moisture:
98. (b) Brown, H. C.; Bhat, N. G.; Srebnik, M. Tetrahedron Lett. 1988, 29, 2631.
99. (c) Oh, C. H.; Jung, S. H. Tetrahedron Lett. 2000, 41, 8513.
100. Matteson, D. S. Tetrahedron 1989, 45, 1859.
101. Stefani, H. A.; Cella, R.; Zukerman-Schpector, J.; Caracelli, I. Z. Kristallogr. NCS 2006, 221, 167.
102. Molander, G. A.; Ham, J. Org. Lett. 2006, 8, 2031.
103. Review: Matteson, D. S. Tetrahedron 1998, 54, 10555.
104. Batey, R. A.; Thadani, A. N.; Smil, D. V. Tetrahedron Lett. 1999, 40, 4289.
105. Batey, R. A.; Thadani, A. N.; Smil, D. V.; Lough, A. J. Synthesis 2000, 990.
106. Frohn, H.-J.; Bardin, V. V. Z. Anorg. Allg. Chem. 2001, 627, 15.
107. Frohn, H.-J.; Bardin, V. V. Z. Anorg. Allg. Chem. 2001, 627, 2499.
108. Molander, G. A.; Hoag, B. P. Organometallics 2003, 22, 3313.
109. Kolomeitsev, A. A.; Kadyrov, A. A.; Szczepkowska-Sztolcman, J.; Milewska, M.; Koroniak, H.; Bissky, G.; Barten, J. A.; Röschenthaler, G.-V. Tetrahedron Lett. 2003, 44, 8273.
110. Welz-Biermann, U.; Ignatyev, N.; Weiden, M.; Schmidt, M.; Heider, U.; Miller, A.; Willner, H.; Sartori, P. (Merck, Gmbh) DE Patent 10216998; U.S. Patent 2005/0131256, 2003; WO Patent 03/2003087113, 2003.
111. Welz-Biermann, U.; Ignatyev, N.; Weiden, M.; Schmidt, M.; Heider, U.; Miller, A.; Willner, H.; Sartori, P. (Merck, Gmbh) DE Patent 10216996; and WO Patent 03/2003, 087020, 2003.
112. Fontani, P.; Carboni, B.; Vaultier, M.; Carrié, R. Tetrahedron Lett. 1989, 30, 4815.
113. (b) (a) Fontani, P.; Carboni, B.; Vaultier M.; Maas, G. Synthesis 1991, 605.
114. Fang, G.-H.; Yan, Z.-J.; Deng, M.-Z. Org. Lett. 2004, 6, 357.
115. Charette, B.; Mathieu, S.; Fournier, J.-F. Synlett 2005, 1779.
116. Reviews on hydroboration: (a) Männig, D.; Nöth, H. Angew. Chem., Int. Ed. 1985, 24, 878.
117. (b) Burgess, K.; Ohlmeyer, M. J. Chem. Rev. 1991, 91, 1179.
118. (c) Beletskaya, I.; Pelter, A. Tetrahedron 1997, 53, 4957.
119. For transition-metal-catalyzed preparation of (Z)-alk-1-enylboron compounds, see: (d) Ohmura, T.; Yamamoto, Y.; Miyaura, N. J. Am. Chem. Soc. 2000, 122, 4990.
120. Petasis, N. A.; Yudin, A. K.; Zavialov, I. A.; Prakash, G. K. S.; Olah, G. A. Synlett 1997, 606.
121. (a) Rasset-Deloge, C.; Martinez-Fresneda, P.; Vaultier, M. Bull. Soc. Chim. Fr. 1992, 129, 285.
122. (b) Kamabuchi, A.; Miyaura, N.; Suzuki, A. Tetrahedron Lett. 1993, 34, 4827.
123. Pereira, S.; Srebnick, M. Organometallics 1995, 14, 3127.
124. Fei, Z.; Zhao, D.; Geldbach, T. J.; Scopelliti, R.; Dyson, P. J. Eur. J. Inorg. Chem. 2005, 860.
125. Brown, H. C.; Bhat, N. G.; Somayaji, V. Organometallics 1983, 2, 1311.
126. Molander, G. A.; Figueroa, R. Org. Lett. 2006, 8, 75.
127. Kalinin, A. V.; Scherer, S.; Snieckus, V. Angew. Chem., Int. Ed. 2003, 42, 3399.
128. Clay, J. M.; Vedejs, E. J. Am. Chem. Soc. 2005, 127, 5766.
129. (a) Ishiyama, T.; Takagi, J.; Ishida, K.; Miyaura, N.; Anastasi, N. R.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 390.
130. (b) Review: Ishiyama, T.; Miyaura, N. J. Organomet. Chem. 2003, 603, 3.
131. (a) Chen, H.; Schlecht, S.; Semple, T. C.; Hartwig, J. F. Science 2000, 287, 1995.
132. (b) Wan, X.; Wang, X.; Luo, Y.; Takami, S.; Kubo, M.; Miyamoto, A. Organometallics 2002, 21, 3703.
133. Murphy, J. M.; Tzschucke, C. C.; Hartwig, J. F. Org. Lett. 2007, 9, 757.
134. Lawrence, J. D.; Takahashi, M.; Bae, C.; Hartwig, J. F. J. Am. Chem. Soc. 2004, 126, 15334.
135. Molander, G. A.; Ribagorda, M. J. Am. Chem Sac. 2003, 125, 11148.
136. Molander, G. A.; Petrillo, D. E. J. Am. Chem. Soc. 2006, 128, 9634.
137. Molander, G. A.; Cooper, D. J. J. Org. Chem. 2007, 72, 3558.
138. Molander, G. A.; Figueroa, R. J. Org. Chem. 2006, 71, 6135.
139. Molander, G. A.; Ham, J.; Canturk, B. Org. Lett. 2007, 9, 821.
140. Molander, G. A.; Sandrock, D. L. Org. Lett. 2007, 9, 1597.
141. Molander, G. A.; Ham, J. Org. Lett. 2006, 8, 2767.
142. For the lithiation of protected boronic acids, see: Dabrowski, M.; Kurach, P.; Lulinski, S.; Serwatowski, J. Appl. Organomet. Chem. 2007, 21, 234.
143. Molander, G. A.; Ellis, N. M. J. Org. Chem 2006, 71, 7491.
144. Roush, W. R.; Walts, A. E.; Hoong, L. K. J. Am. Chem. Soc. 1985, 107, 8186.
145. Kabalka, G. W.; Venkataiah, B.; Dong, G. J. Org. Chem. 2004, 69, 5807.
146. Sebelius, S.; Olsson, V. J.; Szabo, K. J. J. Am. Chem. Soc. 2005, 127, 10478.
147. Kjellgren, J.; Sunden, H.; Szabo, K. J. J. Am. Chem Soc. 2005, 127, 1787.
148. Olsson, V. J.; Sebelius, S.; Selander, N.; Szabó, K. J. J. Am. Chem. Soc. 2006, 128, 4588.
149. Bardin, V. V.; Idemskaya, S. G.; Frohn, H.-J. Z. Anorg. Allg. Chem. 2002, 628, 883.
150. Smoum, R.; Rubinstein, A.; Srebnik, M. Org. Biomol. Chem. 2005, 3, 941.
151. Shundrin, L. A.; Bardin, V. V.; Frohn, H.-J. Z. Anorg. Allg. Chem. 2004, 630, 1253.
152. For X-ray structural determination of potassium organotrifluoroborates, see:
153. (a) Conole, G.; Clough, A.; Whiting, A. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1995, C51, 1056.
154. (b) Kuhn, N.; Fawzi, R.; Kotowski, H.; Steimann, M. Z. Kristallogr.-New Cryst. Struct. 1997, 212, 259.
155. (c) Quach, T. D.; Batey, R. A.; Lough, A. J. Acta Crystallogr., Sect. E: Struct. Rep. OnLine 2001, E57, m320.
156. (d) Thadani, A. N.; Batey, R. A.; Smil, D. V.; Lough, A. J. Acta Crystallogr. Sect. E: Struct. Rep. OnLine 2001, E57, m333.
157. (e) Quach, T. D.; Batey, R. A.; Lough, A. J. Acta Crystallogr., Sect. E: Struct. Rep. OnLine 2001, E57, o688.
158. (f) Bats, J. W.; Scheibitz, M.; Wagner, M. Acta Crystallogn, Sect. C: Cryst. Struct. Commun. 2003, C59, m355.
159. Petrillo, D. E.; Kohli, R. K.; Molander, G. A. J. Am. Soc. Mass Spectrom. 2007, 18, 404.
160. Wang, C.; Mo, Y.; Jang, M.; Janzen, A. F. Can. J. Chem. 1993, 71, 525.
161. Batey, R. A.; Quach, T. D. Tetrahedron Lett. 2001, 42, 9099.
162. Adonin, N. Y.; Bardin, V. V.; Flörke, U.; Frohn, H.-J. Z. Anorg. Allg. Chem. 2005, 631, 2638.
163. Bresner, C.; Aldrige, S.; Fallis, I. A.; Jones, C.; Ooi, L.-L. Angew. Chem., Int. Ed. 2005, 44, 3606.
164. Veverka, M., Putala, M.; Brath, H.; Zupancic, S. (Krka, D. D., Novo Mesto, Slovenia) WO Patent 2007039117, 2007.
165. Matteson, D. S.; Maliakal, D.; Pharazyn, P. S.; Kim, B. J. Synlett 2006, 3501.
166. Frohn, H.-J.; Bailly, F.; Bardin, V. V. Z. Anorg. Allg. Chem. 2002, 628, 723.
167. Billard, T.; Langlois, B. R. J. Org. Chem. 2002, 67, 997.
168. Frohn, H.-J.; Bardin, V. V. J. Organomet. Chem. 2001, 631, 54.
169. Kim, B. J.; Matteson, D. S. Angew. Chem., Int. Ed. 2004, 43, 3056.
170. Gandon, V.; Leca, D.; Aechtner, T.; Vollhardt, K. P. C.; Malacria, M.; Aubert, C. Org. Lett. 2004, 6, 3405.
171. Yuen, K. L.; Hutton, C. A. Tetrahedron Lett. 2005, 46, 7899.
172. Vedejs, E.; Fields, S. C.; Schrimpf, M. R. J. Am. Chem. Soc. 1993, 115, 11612.
173. Shapland, P.; Vedejs, E. J. Org. Chem. 2006, 71, 6666.
174. Review: Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
175. Matteson, D. S. Stereodirected Synthesis with Organoboranes; Springer-Verlag: Berlin, 1995.
176. Thadani, A. N.; Batey, R. A. Org. Lett. 2002, 4, 3827.
177. Brondel, N.; Renoux, B.; Gesson, J.-P. Tetrahedron Lett. 2006, 47, 9305.
178. For boronic Mannich reactions, see: (a) Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445.
179. (b) Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1998, 120, 11798.
180. Petasis, N. A. (Univiversity Southern California, U.S.A.) WO Patent 9800398,1998.
181. Schlienger, N.; Ryce, M. R.; Hansen, T. K. Tetrahedron Lett. 2000, 41, 1303.
182. Petasis, N. A.; Boral, S. Tetrahedron Lett. 2001, 42, 539.
183. Tremblay-Morin, J.-P.; Raeppel, S.; Gaudette, F. Tetrahedron Lett. 2004, 45, 3471.
184. Kabalka, G. W.; Venkataiah, B.; Dong, G. Tetrahedron Lett. 2004, 45, 729.
185. Stas, S.; Tehrani, K. A. Tetrahedron 2007, 63, 8921.
186. For a review, see: Lal, G. S.; Pez, G. P.; Syvret, R. G. Chem. Rev. 1996, 96, 1737.
187. (a) Kabalka, G. W.; Mereddy, A. R. Tetrahedron Lett. 2004, 45, 343.
188. (b) Kabalka, G. W.; Mereddy, A. R. Tetrahedron Lett. 2004, 45, 1417.
189. Kabalka, G. W.; Mereddy, A. R. Organometallics 2004, 23, 4519.
190. (a) Kabalka, G. W.; Mereddy, A. R. Nucl. Med. Biol. 2004, 31, 935.
191. (b) Kabalka, G. W.; Mereddy, A. R. J. Labelled Compd. Radiopharm. 2005, 48, 359.
192. Kabalka, G. W.; Mereddy, A. R.; Green, J. F. J. Labelled Compd. Radiopharm. 2006, 49, 11.
193. (a) Kabalka, G. W. (University of Tennessee Research Fondation, U.S.A.) U.S. Patent 7041859, 2006.
194. (b) Kabalka, G. W.; Tang, G.; Mereddy, A. R. J. Labelled Compd. Radiopharm. 2007, 50, 446.
195. Kerverdo, S.; Gingras, M. Tetrahedron Lett. 2000, 41, 6053.
196. Darses, S.; Brayer, J.-L.; Demoute, J.-P.; Genet, J.-P. Tetrahedron Lett. 1997, 38, 4393.
197. For a review on rhodium-catalyzed carbon-carbon bond-forming reactionsm see: Fagnou, K.; Lautens, M. Chem. Rev. 2003, 103, 169.
198. For palladium-catalyzed cross-coupling of arenediazonium tetrafluoroborates with aryl- and alkenylboronic acids, see: (a) Darses, S.; Jeffery, T.; Brayer, J.-L.; Demoute, J.-P.; Genet, J.-P. Tetrahedron Lett. 1996, 37, 3857.
199. (b) Darses, S.; Jeffery, T.; Brayer, J.-L.; Demoute, J.-P.; Genet, J.-P. Bull. Soc. Chim. Fr. 1996, 133, 1095.
200. (c) Sengupta, S.; Bhattacharyya, S. J. Org. Chem. 1997, 62, 3405.
201. (d) Babudri, F.; Farinola, G. M.; Naso, F.; Panessa, D. J. Org. Chem. 2000, 65, 1554.
202. (e) Willis, D. M.; Strongin, R. M. Tetrahedron Lett. 2000, 41, 6271.
203. (f) Andrus, M. B.; Song, C. Org. Lett. 2001, 3, 3761.
204. (g) Selvakumar, K.; Zapf, A.; Spannenberg, A.; Beller, M. Chem Eur. J. 2002, 8, 3901.
205. For the formation of arenediazonium tetrafluoroborates, see: (a) Roe, A. Organic Syntheses; Wiley and Sons: New York, 1949; Collect. Vol. V, p 193.
206. (b) Suschitzky, H. Advances in Fluorine Chemistry; Butterworths: London, 1965; Vol. 4, p 1.
207. (c) Doyle, M. P.; Bryker, W. J. J. Org. Chem. 1979, 44, 1572.
208. (a) Herrmann, W. A.; Brossmer, C.; Öfele, K.; Reisinger, C. P.; Priermeier, T.; Beller, M.; Fisher, H. Angew. Chem., Int. Ed. 1995, 34, 1844.
209. (b) Beller, M.; Fischer, H.; Herrmann, W. A.; Öfele, K.; Brossmer, C. Angew. Chem., Int. Ed. 1995, 34, 1848.
210. Hunt, A. R.; Stewart, S. K.; Whiting, A. Tetrahedron Lett. 1993, 34, 3599.
211. Gallo, V.; Mastrorilli, P.; Nobile, C. F.; Paolillo, R.; Taccardi, N. Eur. J. Inorg. Chem. 2005, 582.
212. Frohn, H.-J.; Adonin, N. Y.; Bardin, V. V.; Starichenko, V. F. J. Fluorine Chem. 2002, 117, 115.
213. Ma, Y.; Song, C.; Chai, Q.; Ma, C.; Andrus, M. B. Synthesis 2003, 2886.
214. Masllorens, J.; Gonzalez, I.; Roglans, A. Eur. J. Org. Chem. 2007, 158.
215. Xia, M.; Chen, Z.-C. Synth. Commun. 1999, 29, 2457.
216. Xia, M.; Chen, Z.-C. J. Chem. Res. (S) 1999, 400.
217. Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020.
218. Calderwood, D. J.; Johnston, D. N.; Rafferty, P.; Twigger, H. L.; Munschauer, R.; Arnold, L. (Knoll A. G. Chemische Fabriken) WO Patent 9841525, 1998.
219. Puentener, K.; Scalone, M. (Hoffmann-La Roche AG) EP Patent 1057831, 2000.
220. Molander, G. A.; Bernardi, C. R. J. Org. Chem. 2002, 67, 8424.
221. Kabalka, G. W.; Al-Masum, M.; Mereddy, A. R.; Ddush, E. Tetrahedron Lett. 2006, 47, 1133.
222. Molander, G. A.; Brown, A. R. J. Org. Chem. 2006, 71, 9681.
223. Carter, R. R.; Wyatt, J. K. Tetrahedron Lett. 2006, 47, 6091.
224. Milne, J. E.; Buchwald, S. L. J. Am. Chem. Soc. 2004, 126,13028.
225. Kabalka, G. W.; Al-Masum, M. Tetrahedron Lett. 2005, 46, 6329.
226. Arvela, R. K.; Leadbeater, N. E.; Mack, T. L.; Kormos, C. M. Tetrahedron Lett. 2006, 47, 217.
227. Harker, R. L.; Crouch, R. D. Synthesis 2007, 25.
228. (a) Yang, D.; Chen, Y.-C. WO Patent 2005091697, 2005.
229. (b) Chen, W.; Li, R.; Han, B.; Li, B.-J.; Chen, Y.-C.; Wu, Y.; Ding, L.-S.; Yang, D. Eur. J. Org. Chem. 2006, 1177.
230. Wang, L.; Li, P.-H. Chin. J. Chem. 2006, 24, 770.
231. Frohn, H.-J.; Adonin, N. Y.; Bardin, V. V.; Starichenki, V. F. Tetrahedron Lett. 2002, 43, 8111.
232. Korenaga, T.; Kosaki, T.; Kawaushi, Y.; Ema, T.; Sakai, T. J. Fluorine Chem. 2006, 127, 604.
233. Molander, G. A.; Petrillo, D. E.; Landzberg, N. R.; Rohanna, J. C.; Biolatto, B. Synlett 2005, 1763.
234. Kabalka, G. W.; Zhou, L.-L.; Naravane, A. Tetrahedron Lett. 2006, 47, 6887.
235. Barder, T. E.; Buchwald, S. L. Org. Lett. 2004, 6, 2649.
236. Kudo, N.; Perseghini, M.; Fu, G. C. Angew. Chem., Int. Ed. 2006, 45, 1282.
237. Christoforou, C.; Koutentis, P. A.; Rees, C. W. Org. Biomol. Chem. 2003, 1, 2900.
238. (a) O'Brien, C. J.; Kantchev, A. A. B.; Valente, C.; Hadei, N.; Chass, G. A.; Lough, A.; Hopkinson, A. C.; Organ, M. G. Chem. Eur. J. 2006, 12, 4743.
239. (b) O'Brien, C. J.; Organ, M. G.; Kantchev, A. B. (Total Synthesis Ltd, Canada) CA Patent 2556850, 2007.
240. Molander, G. A.; Fumagalli, T. J. Org. Chem. 2006, 71, 5743.
241. Molander, G. A.; Felix, L. A. J. Org. Chem. 2005, 70, 3950.
242. Molander, G. A.; Yokoyama, Y. J. Org. Chem. 2006, 71, 2493.
243. Kabalka, G. W.; Al-Masum, M. Org. Lett. 2006, 8, 11.
244. Kabalka, G. W.; Dadush, E.; Al-Masum, M. Tetrahedron Lett. 2006, 47, 7459.
245. Steinhuebel, D.; Baxter, J. M.; Palucki, M.; Davies, I. W. J. Org. Chem. 2005, 70, 10124.
246. Wu, J.; Zhang, L.; Xia, H.-G. Tetrahedron Lett. 2006, 47, 1525.
247. Kabalka, G. W.; Venkataiah, B.; Dong, G. Org. Lett. 2003, 5, 3803.
248. Molander, G. A.; Sommers, E. M.; Baker, S. R. J. Org. Chem. 2006, 71, 1563.
249. Molander, G. A.; Elia, M. D. J. Org. Chem. 2006, 71, 9198.
250. Zhou, C.; Larock, R. C. J. Org. Chem. 2005, 70, 3765.
251. Alphonse, F.-A.; Suzenet, F.; Keromnes, A.; Lebret, B.; Guillaumet, G. Synlett 2002, 447.
252. Freundlich, J. S.; Landis, H. E. Tetrahedron Lett. 2006, 47, 4275.
253. Molander, G. A.; Pfeiffer, D. Org. Lett. 2001, 3, 361.
254. Molander, G. A.; Vargas, F. Org. Lett. 2007, 9, 203.
255. Yamamoto, Y.; Takada, S.; Miyaura, N. Chem. Lett. 2006, 35, 704.
256. Yamamoto, Y.; Takada, S.; Miyaura, N. Chem. Lett. 2006, 35, 1368.
257. (a) Sonogashira, K. Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 3, p 521.
258. (b) Miyaura, N. Cross-coupling reactions. A practical guide; Springer-Verlag: New York, 2002.
259. Kabalka, G. W.; Naravane, A.; Zhao, L. L. Tetrahedron Lett. 2007, 48, 7091.
260. Kabalka, G. W.; Dong, G.; Venkataiah, B. Tetrahedron Lett. 2005, 46, 763.
261. Kabalka, G. W.; Dong, G.; Venkataiah, B. Tetrahedron Lett. 2004, 45, 5139.
262. Stefani, H. A.; Cella, R.; Dörr, F. A.; Pereira, C. M. P.; Zeni, G.; Gomes, M. Tetrahedron Lett. 2005, 46, 563.
263. Cella, R.; Orfao, A. T. G.; Stefani, H. A. Tetrahedron Lett. 2006, 47, 5075.
264. Cella, R,; Stefani, H. A. Tetrahedron 2006, 62, 5656.
265. Cella, R.; Cunha, R. L. O. R.; Reis, A. E. S.; Pimenta, D. C.; Klitzke, C. F.; Stefani, H. A. J. Org. Chem. 2006, 71, 244.
266. Scalone, M. Private communication.
267. Otake, N.; Haga, Y.; Naya, A.; Mizutani, S.; Kanatani, A. (Banyu Pharmaceutical Co., Ltd., Japan) WO Patent 2005085200, 2005.
268. Chaturvedula, P. V.; Mercer, S. E.; Fang, H. U.S. Patent 2006229447, 2006.
269. Hanazawa, T.; Hirano, M.; Inoue, T.; Nagayama, S.; Nakao, K.; Shishido, Y.; Tanaka, H. (Pfizer Japan Inc., Japan; Pfizer, Inc.) WO Patent 2006097817, 2006.
270. Sakuraba, S.; Moriya, M.; Takahashi, H.; Kishino, H.; Jitsuoka, M.; Kameda, M.; Kanati, A. (Banyu Pharmaceutical Co., Ltd, Japan) WO Patent 2005108399, 2005.
271. Ku, Y.-Y.; Grieme, T. A.; Pu, Y.-M.; Bhatia, A. V.; Toma, P. H.; Henry, R.F.; Hollis, L. S. (Abbott Laboratories, U.S.A.) WO Patent 2005256127, 2005.
272. Li, M.; O'Doherty, G. A. Org. Lett. 2006, 8, 6087.
273. Clemens, R. T.; Jennings, M. P. Chem. Commun. 2006, 2720.
274. Chessari, G.; Congreve, M. S.; Figueroa, N. E.; Frederickson, M.; Murray, C.; Woolford, A. J.-A.; Carr, M. G.; Downham, R.; O'Brien, M. A.; Phillips, T. R.; Woodhead, A. J. (Astex Therapeutics Limited, U.K.) WO Patent 2006109085, 2006.
275. Wallace, E.; W. Yang Hong, J. Blake (Array Biopharma Inc.) WO Patent 2005051302, 2005.
276. Oikawa, N.; Mizuguchi, E.; Morikami, K.; Shimma, N.; Ishii, N.; Tsukaguchi, T.; Ozawa, S. (Chugai Seiyaku Kabushiki Kaisha, Japan) WO Patent 2005080330, 2005.
277. Griesgraber, G. W.; Manske, K. J. (3M Innovative Properties Company, U.S.A.) WO Patent 2006028451, 2006.
278. Auberson, Y.; Betschart, C.; Glatthar, R.; Laumen, K.; Machauer, R.; Tintelnot-Blomley, M.; Troxler, T.; Veenstra, S. J. (Novartis AG, Switzerland) WO Patent 200549585, 2005.
279. Williams, G. D.; Wade, C. E.; Wills, M. Chem. Commun. 2005, 4735.
280. Andrews, S. W.; Guo, X.; Zhu, Z.; Hull, C. E.; Wurster, J. A.; Wang, S.; Wang, E. H.; Malone, T. U.S. Patent 2006004084, 2005.
281. Aicher, T. D.; Chicarelli, M. J.; Gauthier, C. A.; Hinklin, R. J.; Tian, H.; Wallace, O. B.; Krasutsky, A. P.; Allen, J. G. (Eli Lilly and Co., U.S.A.) WO Patent 2006068992, 2006.
282. Chaturvedula, P. V.; Mercer, S. E.; Fang, H. WO Patent 2006052378, 2006.
283. Grisorio, R.; Mastrorilli, P.; Nobile, C. F.; Romanazzi, G.; Suranna, G. P. Tetrahedron Lett. 2005, 46, 2555.
284. Grisorio, R.; Suranna, G. P.; Mastrorilli, P.; Nobile, C. F. Org. Lett. 2007, 9, 3149.
285. Grisorio, R.; Mastrorilli, P.; Nobile, C. F.; Romanazzi, G.; Suranna, G. P.; Gigli, G.; Piliego, C.; Ciccarella, G.; Cosma, P.; Acierno, D.; Amendola, E. Macromolecules 2007, 40, 4865.
286. Sakai, N.; Sisson, A. L.; Bhosale, S.; Füjrstenberg, A.; Baneiji, N.; Vauthey, E.; Matile, S. Org. Biomol. Chem. 2007,5, 2560.
287. Pagano, N.; Maksimoska, J.; Bregman, H.; Williams, D. S.; Webster, R. D.; Xue, F.; Meggers, E. Org. Biomol. Chem. 2007, 5, 1218.
288. Holloway, M. K.; Liverton, N. J.; McCauley, J. A.; Rudd, M. T.; Vacca, J. P.; Ludmerer, S. W.; Olsen, D. B. (Merck & Co., Inc., U.S.A.) WO Patent 2007016441, 2007.
289. (a) Mizutani, T.; Nagase, T.; Sato, N.; Kanatani, A.; Tokita, S. (Banyu Pharmaceutical Co., Ltd, Japan) WO Patent 2005115993, 2005.
290. (b) Sato, Y.; Kurihara, H.; Kamijo, K.; Onozaki, Y.; Tsujino, T.; Sugimoto, T.; Watanabe, A.; Mitsuya, M.; Komatani, H. (Banyu Pharmaceutical Co., Ltd, Japan) WO Patent 2006049339, 2006.
291. (c) Murakami, T.; Kawano, T.; Shiraki, R.; Ishii, H.; Yoshimura, S.; Ohkawa, T.; Hosaka, M.; Fukudome, H.; Inoki, Y. (Astellas Pharma Inc., Japan) WO Patent 2006030805, 2006.
292. (d) Jitsuoka, M.; Sato, N.; Tsukahara, D.; Ohtake, N.; Tokita, S. (Banyu Pharmaceutical Co., Ltd., Japan) WO Patent 2006028239, 2006.
293. (e) Kawamura, M.; Hashihayata, T.; Sunami, S.; Sugimoto, T.; Yamamoto, F.; Sato, Y.; Kamijo, K.; Mitsuya, M.; Iwasawa, Y.; Komatani, H. (Banyu Pharmaceutical Co., Ltd, Japan) WO Patent 2006025567, 2006.
294. 215 (f) Naganuma, K.; Yokoi, H. (Asahi Kasei Pharma Corp., Japan) WO Patent 2006123639, 2006.
295. 216 Maillaird, M.; Hom, C.; Gailunas, A.; Jagodzinska, B.; Fang, L. Y.; John, V.; Freskos, J. N.; Pulley, S. R.; Beck, J. P.; Tenbrink, R. E. (Elan Pharmaceutical Inc., Pharmacia & Upjohn Co.) WO Patent 200202512, 2002.
296. 217 Armitt, D. J.; Crisp, G. T. Tetrahedron 2006, 62, 1485.
297. Thompson, W.; Young, S. D.; Phillips, B. T.; Munson, P.; Whitter, W.; Liverton, N.; Dieckhaus, C.; Butcher, J.; Mc Cauley, J. A.; Mc Intyre, C.; Layton, M. E.; Sanderson, P. E. (Merck & Co. Inc.) WO Patent 2005019221, 2005.
298. Molander, G. A.; Debinel, F. J. Am. Chem. Soc. 2004, 126, 10313.
299. Huffman, J. W.; Padgett, L. W.; Isherwood, M. L.; Wiley, J. L.; Martin, B. R. Bioorg. Med. Chem. 2006, 16, 5432.
300. Pelcman, B.; Olofsson, K.; Katkevics, M.; Ozola, V.; Suna, E.; Kalvins, I.; Trapencieris, P. (Biolipox AB, Sweden) WO Patent 2006077364, 2006.
301. Skaff, O.; Jolliffe, K. A.; Hutton, C. A. J. Org. Chem. 2005, 70, 7353.
302. Garcia-Fortanet, J.; Debergh, J. R.; De Brabander, J. K. Org. Lett. 2005, 7, 685.
303. Tremblay-Morin, J.-P.; Ali, H.; van Lier, J. E. Tetrahedron Lett. 2006, 47, 3043.
304. Ali, H.; St-Jean, O.; Tremblay-Morin, J.-P.; van Lier, J. E. Tetrahedron Lett. 2006, 47, 8275.
305. Ragab, H. M.; Kim, J. S.; Dukat, M.; Navarro, H.; Glennon, R. A. Bioorg. Med. Chem. Lett. 2006, 16, 4283.
306. Plettenburg, O.; Hofmeister, A.; Kadereit, D.; Peukert, S.; Ruf, S.; Ritter, K.; Loehn, M.; Ivashchenko, Y.; Monecke, P.; Dreyer, M.; Karmt, A. (Sanofi-Aventis Deutschland QmbH, Germany) WO Patent 2007000240, 2007.
307. Kozikowski, A.; Kurome, T.; Setola, V.; Roth, B. (University of Illinois, Chicago, IL, U.S.A.) WO Patent 2007025144, 2007.
308. Füjrstner, A.; Larionov, O.; Flügge, S. Angew. Chem., Int. Ed. 2007, 46, 5545.
309. Harvey, J. H.; Butler, B. K.; Trauner, D. Tetrahedron Lett. 2007, 48, 1661.
310. Review: Szabó, K. J. Chem. Eur. J. 2004, 10, 5268.
311. (a) Solin, N.; Wallner, O. A.; Szabó, K. J. Org. Lett. 2005, 7, 689.
312. (b) Wallner, O. A.; Szabó, K. J. Chem. Eur. J. 2006, 12, 6976.
313. Aydin, J.; Kumar, S.; Sayath, M. J.; Wallner, O. A.; Szabó, K. J. J, Org. Chem. 2007, 72, 4689.
314. Reviews: (a) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046.
315. Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576,
316. (a) Chan, D. M. T.; Monaco, K. L.; Wang, R. P. Tetrahedron Lett. 1998, 39, 2933.
317. (b) Evans, D. A.; Katz, J. L.; West, T. R. Tetrahedron Lett. 1998, 39, 2937.
318. Quach, T. D.; Batey, R. A. Org. Lett. 2003, 5, 1381.
319. Tomperi, J.; Salo, H.; Kallatsa, O.; Knuuttila, P.; Laakso, P.; Hoeglund, L.; Hoffren, A.-M.; Kokko, K.; Saarenketo, P.; Engstroem, M.; Wurster, S. (Oy Juvantia Pharma Ltd., Finland) WO Patent 123020, 2006.
320. Granander, J.; Eriksson, J.; Hilmersson, G. Tetrahedron: Asymmetry 2006, 17, 2021.
321. Quach, T. D.; Batey, R. A. Org. Lett. 2003, 5, 4397.
322. Alcalde, E.; Dinarès, I.; Rodriguez, S.; Garcia de Miguel, C. Eur. J. Org. Chem. 2005, 1637.
323. Kabalka, G. W.;, Zhou, L.-L. Lett. Org. Chem. 2006, 3, 320.
324. Le Bourdonnec, B.; Googman, A. J.; Graczyk, T. M.; Belanger, S.; Seida, P. R.; DeHaven, R. N.; Dolle, R. E. J. Med. Chem. 2006, 49, 7290.
325. Wang, L.; Wang, M.; Huang, F. Synlett 2005, 2007.
326. Reviews: (a) Krause, N.; Hoffmann-Röder, A. Synthesis 2001, 171.
327. (b) Sibi, M. P.; Manyem, S. Tetrahedron 2000, 56, 8033.
328. For reviews on rhodium-catalyzed addition of organoboranes to unsaturated substrates, see: (a) Hayashi, T. Synlett 2001, 879.
329. (b) Hayashi, T.; Yarnasaki, K. Chem. Rev. 2003, 103, 2829.
330. (c) Hayashi, T. Bull. Chem. Soc. Jpn. 2004, 77 13.
331. (d) Hayashi, T. Pure Appl. Chem. 2004, 76, 465.
332. (a) Batey, R. A.; Thadani, A. N.; Smil, D. V. Org. Lett. 1999, 1, 1683.
333. (b) Thadani, N.; Batey, R. A.; Smil, D. V. CA Patent 2285578, 1999.
334. (a) Pucheault, M.; Darses, S.; Genet, J.-P. Tetrahedron Lett. 2002, 43, 6155.
335. (b) Pucheault, M.; Darses, S.; Genet, J.-P. Eur. J. Org. Chem. 2002, 3552.
336. Pucheault, M.; Michaud, V.; Darses, S.; Genet, J.-P. Tetrahedron Lett. 2004, 45, 4729.
337. Navarre, L.; Pucheault, M.; Darses, S.; Genet, J.-P. Tetrahedron Lett. 2005, 46, 4247.
338. (a) Sakuma, S.; Nhyaura, N. J. Org. Chem. 2001, 66, 8944.
339. (b) Senda, T.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 2001, 66, 6852.
340. Navarre, L.; Darses, S.; Genet, J.-P. Eur. J. Org. Chem. 2004, 69.
341. Castaldi, G.; Colombo, L.; Rossi, R.; Allegrini, P. (Dipharma S.p.A., Italy) CA Patent 2502640, 2005.
342. Ma, Y.; Song, C.; Ma, C.; Sun, Z.; Chai, Q.; Andrus, M. B. Angew. Chem., Int. Ed. 2003, 42, 5871,
343. (a) Duursma, A.; Lefort, L.; Boogers, J. A. F.; de Vries, A. H. M.; de Vries, J. G.; Minnard, A. J.; Feringa, B. L. Org. Biomol. Chem. 2004, 2, 1682.
344. (b) Duursma, A.; Boiteau, J.-G.; Lefort, L.; Boogers, J. A. F.; de Vries, A. H. M.; de Vries, J. G.; Minnard, A. J.; Feringa, B. L. J. Org. Chem. 2004, 69, 8045.
345. Tokunaga, N.; Hayashi, T. Adv. Synth. Catal. 2007, 349, 513.
346. Nishikata, T.; Yamamoto, Y.; Miyaura, N. Angew. Chem., Int. Ed. 2003, 42, 2768.
347. (a) Nishikata, T.; Yamamoto, Y.; Miyaura, N. Chem. Lett., 2005 34, 720.
348. (b) Nishikata, T.; Yamamoto, Y.; Gridnev, J. D.; Miyaura, N. Organometallics 2005, 24, 5025.
349. Navarre, L.; Darses, S.; Genet, J.-P. Angew. Chem., Int. Ed. 2004, 43, 719.
350. Moss, R. J.; Wadsworth, K. J.; Chapman, C. J.; Frost, C. G. Chem. Commun. 2004, 1984.
351. Martinez, R.; Voica, F.; Genet, J.-P.; Darses, S. Org. Lett. 2007, 9, 3213.
352. Navarre, L.; Darses, S.; Genet, J.-P. Adv. Synth. Catal. 2006, 348, 317.
353. Navarre, L.; Darses, S.; Genet, J.-P. Chem. Commun. 2004, 1108.
354. Wu, J.; Zhang, L.; Luo, Y. Tetrahedron Lett. 2006, 47, 6747.
355. Abbiati, G.; Areadi, A.; Marinelli, F.; Rossi, E.; Verdecchia, M. Synlett 2006, 3218.
356. For reviews,see: (a) Evans, D.A. Science 1988, 240, 420.
357. (b) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. 1991, 30, 49.
358. (c) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833.
359. (d) Pu, L.; Yu, H. B. Chem. Rev. 2001, 101, 757.
360. (a) Oi, S.; Moro, M.; Inoue, Y. Chem. Commun. 1997, 1621.
361. (b) Li, C.-J.; Meng, Y. J. Am. Chem. Soc. 2000, 122, 9538.
362. (c) Huang, T.; Meng Y.; Venkatraman, S.; Wang, D.; Li, C.-J. J. Am. Chem. Soc. 2001, 123, 7451.
363. (d) Oi, S.; Moro, M.; Fukuhara, H.; Kawanishi, T.; Inoue, Y. Tetrahedron 2003, 59, 4351.
364. (a) Oi, S.; Moro, M.; Inoue, Y. Organometallics 2001, 20, 1036.
365. (b) Murata, M.; Shimazaki, R.; Ishikura, M.; Watanabe, S.; Masuda, Y. Synthesis 2002, 717.
366. (a) Sakai, M.; Ueda, M.; Miyaura, N. Angew. Chem., Int. Ed. 1998, 37, 3279.
367. (b) Ueda, M.; Miyaura, N. J. Org. Chem. 2000, 65, 4450,
368. (c) Fürstner, A.; Krause, H. Adv. Synth. Catal. 2001, 343, 343.
369. (d) Moreau, C.; Hague, C.; Weller, A. S.; Frost, C. G. Tetrahedron Lett. 2001, 42, 6957.
370. (e) Imlinger, N.; Mayr, M.; Wang, D.; Wurst, K.; Buchmeiser, M. R. Adv. Synth. Catal. 2004, 346, 1836.
371. (f) Özdemir, I.; Gürbüz, N.; Seçkin, T.;
372. Pucheault, M.; Darses, S.; Genet, J.-P. Chem. Commun. 2005, 4714.
373. Bolshan, Y.; Batey, R. A. Org. Lett. 2005, 7, 1481.
374. Pucheault, M.; Darses, S.; Genet, J.-P. J. Am. Chem. Soc. 2004, 126, 15356.
375. Sakurai, H.; Tsunoyama, H.; Tsukuda, T. J. Organomet. Chem. 2007, 692, 368.