CF3-bearing aromatic and heterocyclic building blocks

Angewandte Chemie - International Edition

Volumn 45, Issue 33, 2006, Pages 5432-5446

  Schlosser, Manfred ^a,b  

^a Institut de chimie moleculaire et biologique Ecole Polytechnique Federale de Lausanne   (Switzerland)

^b UNIVERSITY OF LAUSANNE   (Switzerland)

Author keywords

Coupling reactions; Metalation; Organofluorine compounds; Synthetic methods; Trifluoromethyl groups

Indexed keywords

COUPLING REACTIONS; METALATION; ORGANOFLUORINE COMPOUNDS; SYNTHETIC METHODS; TRIFLUOROMETHYL GROUPS;

INDUSTRIAL RESEARCH; MOLECULAR STRUCTURE; ORGANIC COMPOUNDS; SUBSTITUTION REACTIONS;

FLUORINE COMPOUNDS;

AROMATIC HYDROCARBON; CHLOROFLUOROCARBON; FLUOROFORM; HETEROCYCLIC COMPOUND;

CHEMICAL STRUCTURE; CHEMISTRY; REVIEW;

CHLOROFLUOROCARBONS, METHANE; HETEROCYCLIC COMPOUNDS; HYDROCARBONS, AROMATIC; MOLECULAR STRUCTURE;

EID: 33748661487     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200600449     Document Type: Review

References (170)

1. a) D. B. Harper, D. O'Hagan, Nat. Prod. Rep. 1994, 11, 123-133
2. [Chem. Abstr. 1994, 121, 204 996] ;
3. b) D. O'Hagan, D. B. Harper, J. Fluorine Chem. 1999, 100, 127-133.
4. S. Rozen in Organo-Fluorine Compounds (Houben-Weyl: Methods of Organic Chemistry, Vol. E10a, Thieme, Stuttgart, 2000), pp. 167-187.
5. K. Pohmer, A. Bulan in Organo-Fluorine Compounds (Houben-Weyl: Methods of Organic Chemistry, Vol. E10a, Thieme, Stuttgart, 2000), pp. 305-320.
6. M. Zupan in Organo-Fluorine Compounds (Houben-Weyl: Methods of Organic Chemistry, Vol. E10a, Thieme, Stuttgart, 2000), pp. 265-269.
7. G. G. Furin in Organo-Fluorine Compounds (Houben-Weyl: Methods of Organic Chemistry, Vol. E10a, Thieme, Stuttgart, 2000), pp. 432-499.
8. a) S. G. Lal, J. Org. Chem. 1993, 58, 2791-2796;
9. b) D. P. Matthews, S. C. Miller, E. T. Jarvi, J. S. Sabol, J. R. McCarthy, Tetrahedron Lett. 1993, 34, 3057-3060;
10. c) R. E. Banks, I. Sharif, R. G. Pritchard, Acta Crystallogr. Sect. C 1993, 49, 492-495
11. [Chem. Abstr. 1993, 118, 223 259];
12. d) R. E. Banks, N. J. Lawrence, A. L. Popplewell, J. Chem. Soc. Chem. Commun. 1994, 343-344;
13. e) P. T. Nyffeler, S. G. Durón, M. D. Burkart, S. P. Vincent, C.-H. Wong, Angew. Chem. 2005, 117, 196-217;
14. Angew. Chem. Int. Ed. 2005, 44, 192-212.
15. a) W. Barnette, J. Am. Chem. Soc. 1984, 106, 452-454;
16. b) S. H. Lee, J. Schwartz, J. Am. Chem. Soc. 1986, 108, 2445-2447.
17. R. Mietchen, D. Peters in Organo-Fluorine Compounds (Houben-Weyl: Methods of Organic Chemistry, Vol. E10a, Thieme, Stuttgart, 2000), pp. 95-158.
18. a) G. A. Boswell, W. C. Ripka, Org. React. 1974, 21, 1-124;
19. b) W. Dmowski in Organo-Fluorine Compounds (Houben-Weyl: Methods of Organic Chemistry, Vol. E10a, Thieme, Stuttgart, 2000), pp. 321-394.
20. a) M. Hudlicky, Org. React. 1988, 35, 513-637;
21. b) M. H. Rock in Organo-Fluorine Compounds (Houben-Weyl: Methods of Organic Chemistry, Vol. E10a, Thieme, Stuttgart, 2000), pp. 167-187.
22. a) P. A. Messina, K. C. Mange, W. J. Middleton, J. Fluorine Chem. 1989, 42, 137-143;
23. b) G. S. Lal, G. P. Pez, R. J. Pasaresi, F. M. Prozonic, J. Org. Chem. 1999, 64, 7048-7054;
24. c) P. R. Singh, J. M. Shreeve, Synthesis 2002, 2561-2578.
25. L. R. Subramanian, G. Siegemund in Organo-Fluorine Compounds (Houben-Weyl: Methods of Organic Chemistry, Vol. E10a, Thieme, Stuttgart, 2000), pp. 548-596.
26. L. M. Yagupolskii in Organo-Fluorine Compounds (Houben-Weyl: Methods of Organic Chemistry, Vol. E10a, Thieme, Stuttgart, 2000), pp. 509-534.
27. a) P. Gölitz, A. de Meijere, Angew. Chem. 1977, 89, 892-893;
28. Angew. Chem. Int. Ed. Engl. 1977, 16, 854-855;
29. b) V. Hartkopf, A. de Meijere, Angew. Chem. 1982, 94, 444;
30. Angew. Chem. Int. Ed. Engl. 1982, 21, 443.
31. a) P. Osswald, F. Müller, F. Steinhäuser (IG Farben), DRP 575593, 1931; Chem. Zbl. 1933II, 609;
32. b) J. H. Simons, C. J. Lewis, J. Am. Chem. Soc. 1938, 60, 492-497;
33. c) O. Scherer, Angew. Chem. 1939, 52, 457-459;
34. d) W. A. Sheppard, C. M. Sharts, Organic Fluorine Chemistry, Benjamin, New York, 1969, pp. 71-81;
35. e) U. Horn, F. Mutterer, C. D. Weis, Helv. Chim. Acta 1976, 59, 190-211;
36. f) G. A. Olah, J. T. Welch, Y. D. Vankar, M. Nojima, I. Kerekes, J. A. Olah, J. Org. Chem. 1979, 44, 3872-3881;
37. g) R. Nishiyama, K. Fujikawa, I. Yokomichi, T. Yasuhiro, S. Nishimura (Ishihara Sangyo Kasei), Jpn. Kokai Tokkyo Koho JP 55085564, 1978 [Chem. Abstr. 1981, 94, 47 146];
38. h) T. Fukuhara, N. Yoneda, Chem. Lett. 1993, 509-512;
39. i) L. M. Yagupolskii, D. V. Fedyuk, K. I. Petko, V. I. Troitskaya, V. I. Rudyk, V. V. Rudyuk, J. Fluorine Chem. 2000, 106, 181-187.
40. a) W. R. Hasek, W. C Smith, V. A. Engelhardt, J. Am. Chem. Soc. 1960, 82, 543-551;
41. b) M. S. Raasch, J. Org. Chem. 1962, 27, 1406-1409;
42. c) D. G. Martin, F. Kagan, J. Org. Chem. 1962, 27, 3164-3168;
43. d) M. P. Mertens, S. E. Saheb, J. Heterocycl. Chem. 1965, 2, 491-491;
44. e) Y. Kobayashi, I. Kumadaki, S. Taguchi, Chem. Pharm. Bull. 1969, 17, 2335-2339.
45. a) M. Kuroboshi, K. Kanie, T. Hiyama, Adv. Synth. Catal. 2001, 343, 235-250;
46. b) M. Shimizu, T. Hiyama, Angew. Chem. 2005, 117, 218-234;
47. Angew. Chem. Int. Ed. 2005, 44, 214-231.
48. M. Schlosser, B. Spahić, C Le Van, Helv. Chim. Acta 1975, 58, 2586-2594.
49. a) M. Kuroboshi, N. Yamada, Y. Tokebe, T. Hiyama, Synlett 1995, 987-988;
50. b) M. Shimizu, N. Yamada, Y. Takebe, T. Hata, M. Kuroboshi, T. Hiyama, Bull. Soc. Chim. Jpn. 1998, 71, 2903-2921.
51. a) R. Krishnamurti, D. R. Bellew, G. K. S. Prakash, J. Org. Chem. 1991, 56, 984-989;
52. b) J. Wiedemann, T. Heiner, G. Mloston, G. K. S. Prakash, G. A. Olah, Angew. Chem. 1998, 110, 880-881;
53. Angew. Chem. Int. Ed. 1998, 37, 820-821;
54. c) R. P. Singh, J. M. Shreeve, Tetrahedron 2000, 56, 7613-7632.
55. a) B. Folléas, I. Marek, J.-F. Normant, L. Saint-Jalmes, Tetrahedron 2000, 56, 275-283;
56. b) B. R. Langlois, T. Billard, Synthesis 2003, 185-194.
57. V. C. R. McLoughlin, I. Thrower, Tetrahedron 1969, 25, 5921-5940.
58. a) Y. Kobayashi, I. Kumadaki, Tetrahedron Lett. 1969, 10, 4095-4096;
59. b) Y. Kobayashi, I. Kumadaki, S. Sato, N. Hara, E. Chikami, Chem. Pharm. Bull. 1970, 18, 2334-2339;
60. c) Y. Kobayashi, I. Kumadaki, A. Ohsawa, T. Yamada, Chem. Pharm. Bull. 1972, 20, 1839-1839;
61. d) Y. Kobayashi, I. Kumadaki, Y. Hanzawa, Chem. Pharm. Bull. 1977, 25, 3009-3012;
62. e) Y. Kobayashi, K. Yamamoto, T. Asai, M. Nakano, I. Kumadaki, J. Chem. Soc. Perkin Trans. 1 1980, 2755-2762.
63. N. V. Konderatenko, E. P. Vechirko, L. M. Yagupolskii, Synthesis 1980, 932-933.
64. a) K. Matsui, E. Tobita, M. Ando, K. Kondo, Chem. Lett. 1981, 1719-1720;
65. b) H. Suzuki, Y. Yoshida, A. Osuka, Chem. Lett. 1982, 135-136;
66. c) Q.-Y. Chen, S.-W. Wu, J. Chem. Soc. Chem. Commun. 1989, 705-706.
67. a) D. J. Burton, D. M. Wiemers, J. Am. Chem. Soc. 1985, 107, 5014-5015;
68. b) D. M. Wiemers, D. J. Burton, J. Am. Chem. Soc. 1986, 108, 832-834.
69. H. Urata, T. Fuchikami, Tetrahedron Lett. 1991, 32, 91-94.
70. a) I. Ruppert, K. Schlich, W. Volbach, Tetrahedron Lett. 1984, 25, 2195-2198;
71. b) G. Pawelke, J. Fluorine Chem. 1989, 42, 429-433.
72. a) G. K. S. Prakash, R. Krishnamurti, G. A. Olah, J. Am. Chem. Soc. 1989, 111, 393-395;
73. b) G. P. Stahly, D. R. Bell, J. Org. Chem. 1989, 54, 2873-2877;
74. c) V. Broicher, D. Geffken, Tetrahedron Lett. 1989, 30, 5243-5244.
75. F. Cottet, M. Schlosser, Eur. J. Org. Chem. 2002, 327-330.
76. E. Masson, E. Marzi, F. Cottet, C. Bobbio, M. Schlosser, Eur. J. Org. Chem. 2005, 4393-4400.
77. B. V. Kunshenko, L. A. Alekseeva, L. M. Yagupolskii, Zh. Org. Khim. 1972, 8, 830-834
78. [Chem. Abstr. 1972, 77, 19 423].
79. D. Bonnet-Delpon, M. Charpentier-Morize, R. Jacquot, J. Org. Chem. 1988, 53, 759-762.
80. M. Kuroboshi, T. Hiyama, Chem. Lett. 1992, 827-830.
81. Z.-Y. Long, J.-X Duan, Y.-B. Lin, C. Y. Guo, Q.-Y. Chen, J. Fluorine Chem. 1996, 78, 177-181.
82. A. H. El-Sagheer, E. E.-D. M. Salem, J. M. Mellor, Tetrahedron Lett. 2000, 41, 7383-7386.
83. V. P. Le, P. R. Wells, Aust. J. Chem. 1992, 45, 1057-1061.
84. F. Bailly, F. Cottet, M. Schlosser, Synthesis 2005, 791-797.
85. M. Schlosser, E. Castagnetti, Eur. J. Org. Chem. 2001, 3991-3997.
86. E. Masson, M. Schlosser, Eur. J. Org. Chem. 2005, 4401-4405.
87. F. Mongin, O. Desponds, M. Schlosser, Tetrahedron Lett. 1996, 37, 2767-2770.
88. "Topics in Drug Design and Discovery": A. A. Patchett, R. P. Nargund, Annu. Rep. Med. Chem. 2000, 35, 289-298
89. [Chem. Abstr. 2000, 133, 317 128].
90. a) A. Daştan, U. Demir, M. Balci, J. Org. Chem. 1994, 59, 6534-6538;
91. b) A. Altundas, A. Daştan, M. M. McKee, M. Balci, Tetrahedron 2000, 56, 6115-6120;
92. c) A. Daştan, E. Uzundumlu, M. Balci, Helv. Chim. Acta 2002, 85, 2729-2739.
93. F. Cottet, E. Castagnetti, M. Schlosser, Synthesis 2005, 798-803.
94. a) J. T. B. H. Jastrzebski, G. van Koten, K. Goubitz, C. Arlen, M. Pfeffer, J. Organomet. Chem. 1983, 246, C75-C79;
95. b) C. Kiefl, A. Mannscheck, Synthesis 1995, 1033-1037.
96. a) R. L. Gay, C. R. Hauser, J. Am. Chem. Soc. 1967, 89, 2297-2303;
97. b) M. Julia, M. Duteil, J. Y. Lallemand, J. Organomet. Chem. 1975, 102, 239-243;
98. c) Z. Horii, Y. Matsumoto, T. Momose, Chem. Pharm. Bull. 1971, 19, 1245-1256.
99. M. Schlosser, Eur. J. Org. Chem. 2001, 3975-3984, especially 3977-3978.
100. a) M. Schlosser, S. Strunk, Tetrahedron Lett. 1984, 25, 741-744;
101. b) M. Schlosser, H. Geneste, Chem. Eur. J. 1998, 4, 1969-1973.
102. M. Schlosser, Angew. Chem. 2005, 117, 380-398;
103. Angew. Chem. Int. Ed. 2005, 44, 376-393.
104. M. Schlosser, ACS Symp. Ser. 2005, 911, 218-231.
105. E. Marzi, C. Bobbio, F. Cottet, M. Schlosser, Eur. J. Org. Chem. 2005, 2116-2123.
106. a) I. F. Tupytsin, N. K. Seminova, Tr. Gos. Inst. Prikl. Khim. 1962, 49, 120-132
107. [Chem. Abstr. 1964, 60, 6721c];
108. b) J. A. Zoltewicz, C. L. Smith, J. Am. Chem. Soc. 1967, 89, 3358-3359;
109. c) J. A. Zoltewicz, G. Grahe, C. L. Smith, J. Am. Chem. Soc. 1969, 91, 5501-5505;
110. d) I. F. Tupitsyn, N. N. Zatspina, A. V. Kirova, Y. L. Kaminskii, A. G. Ivanenko, Reakts. Sposobn. Org. Soedin. 1973, 10, 143-162
111. [Chem. Abstr. 1973, 79, 114 928v].
112. P. Gros, Y. Fort, P. Caubère, J. Chem. Soc. Perkin Trans. 1 1998, 1685-1689.
113. a) G. Katsoulos, S. Takagishi, M. Schlosser, Synlett 1992, 360-362;
114. b) M. Schlosser, F. Faigl, L. Franzini, H. Geneste, G. Katsoulos, G.-f. Zhong, Pure Appl. Chem. 1994, 66, 1439-1446;
115. c) F. Mongin, R. Maggi, M. Schlosser, Chimia 1996, 50, 650-652.
116. M. Schlosser in Organometallics in Synthesis: A Manual (Ed.: M. Schlosser), 2nd ed., Wiley, Chichester, 2002, pp. 1-352, especially 253-259.
117. F. Cottet, M. Marull, F. Mongin, D. Espinosa, M. Schlosser, Synthesis 2004, 1619-1624.
118. F. Cottet, M. Schlosser, Eur. J. Org. Chem. 2004, 3793-3798.
119. F. Cottet, M. Schlosser, Tetrahedron 2004, 60, 11 869-11 874.
120. M. Schlosser, T. Rausis, Eur. J. Org. Chem. 2004, 1018-1024.
121. T. Iida, T. Wada, K. Tomimoto, T. Mase, Tetrahedron Lett. 2001, 42, 4841-4844.
122. A. Inoue, K. Kitagawa, H. Shinokubo, K. Oshima, J. Org. Chem. 2001, 66, 4333-4339.
123. M. Schlosser, M. Marull, Eur. J. Org. Chem. 2003, 1567-1575.
124. C. Eaborn, J. Organomet. Chem. 1975, 100, 43-57.
125. M. Marull, M. Schlosser, Eur. J. Org. Chem. 2003, 1576-1588.
126. O. Lefebvre, M. Marull, M. Schlosser, Eur. J. Org. Chem. 2003, 2115-2121.
127. M. Marull, O. Lefebvre, M. Schlosser, Eur. J. Org. Chem. 2004, 54-63.
128. T. J. Kress, J. Org. Chem. 1979, 44, 2081-2082.
129. L. Ondi, O. Lefebvre, M. Schlosser, Eur. J. Org. Chem. 2004, 3714-3718.
130. M. Schlosser, O. Lefebvre, L. Ondi, Eur. J. Org. Chem. 2006, 1593-1598.
131. M. Schlosser, J.-N. Volle, F. Leroux, K. Schenk, Eur. J. Org. Chem. 2002, 2913-2920.
132. a) D. A. Shirley, P. A. Roussel, J. Am. Chem. Soc. 1953, 75, 375-378;
133. b) R. J. Sundberg, H. R. Russel, J. Org. Chem. 1973, 38, 3324-3330;
134. c) R. J. Sundberg, R. L. Parton, J. Org. Chem. 1976, 41, 163-165;
135. d) I. Hasan, E. R. Marinelli, L.-C. C. Lin, F. W. Fowler, A. B. Levy, J. Org. Chem. 1981, 46, 157-164.
136. J. A. Joule, K. Mills, G. F. Smith, Heterocyclic Chemistry, 3rd ed., Stanley Thornes, Cheltenham, 1998, pp. 307-320.
137. a) M. Schlosser, A. Ginanneschi, F. Leroux, manuscript in preparation;
138. b) A. Ginanneschi, Dissertation, Ecole Polytechnique Fédé rale, Lausanne, 2005.
139. G. Bartoli, G. Palmieri, Tetrahedron Lett. 1989, 30, 2129-2132.
140. a) P. J. Montagne, Recl. Trav. Chim. Pays-Bas 1920, 39, 483-491, 492-494;
141. b) M. Tashiro, G. Fukata, J. Org. Chem. 1977, 42, 835-838;
142. c) L. B. Fertel, N. J. O'Reilly, K. M. Callaghan, J. Org. Chem. 1993, 58, 261-263;
143. d) C. Bobbio, M. Schlosser, J. Org. Chem. 2005, 70, 3039-3045.
144. a) M. Schlosser, D. Michel, Tetrahedron 1996, 52, 99-108;
145. b) M. Schlosser in Enantiocontrolled Synthesis of Fluoroorganic Compounds: Stereochemical Challenges and Biomedicinal Targets (Ed.: V. A. Soloshonok), Wiley, Chichester, 1999, pp. 613-659;
146. c) F. Grein, J. Phys. Chem. A 2002, 106, 3823-3827;
147. d) F. Leroux, ChemBioChem 2004, 5, 644-649.
148. M. Schlosser, Angew. Chem. 1998, 110, 1538-1556;
149. Angew. Chem. Int. Ed. 1998, 37, 1496-1513.
150. J. D. Dunitz, ChemBioChem 2004, 5, 614-621.
151. a) B. E. Smart in Organofluorine Chemistry: Principles and Commercial Applications (Eds.: R. E. Banks, B. E. Smart, J. C. Tatlow), Plenum, New York, 1994, pp. 57-88, especially 64-65;
152. b) J. C. Biffinger, H. W. Kim, S. G. DiMagno, ChemBioChem 2004, 5, 622-627.
153. a) F. L. M. Pattison, R. L. Buchanan, F. H. Dean, Can. J. Chem. 1965, 43, 1700-1713;
154. b) J. Fried, D. K. Mitra, M. Nagarajan, M. M. Mehrota, J. Med. Chem. 1980, 23, 234-237;
155. c) P. H. Stern, Y. Tanaka, H. F. DeLuca, N. Ikekawa, Y. Kobayashi, Mol. Pharmacol. 1981, 20, 460-462
156. [Chem. Abstr. 1982, 96, 46 392q];
157. d) K. Bannai, T. Toru, T. Oba, T. Tanaka, N. Okamura, K. Watanabe, A. Hazato, S. Kurozumi, Tetrahedron 1983, 39, 3807-3819;
158. e) J. Fried, E. A. Hallinan, M. J. Szewedo, J. Am. Chem. Soc. 1984, 106, 3871-3872;
159. f) J. G. Dingwall, Pestic. Sci. 1994, 41, 259-267
160. [Chem. Abstr. 1994, 212, 127 765a];
161. lecture held as part of the conference Fluorine in the Service of Man, University of Manchester, January 9-11, 1995;
162. g) T. Nakano, M. Makino, Y. Morizawa, Y. Matsumura, Angew. Chem. 1996, 108, 1082-1084;
163. Angew. Chem. Int. Ed. Engl. 1996, 35, 1019-1021;
164. h) S. G. DiMagno, P. H. Dussault, J. A. Schultze, J. Am. Chem. Soc. 1996, 118, 5312-5313;
165. i) P. H. Buist, K. A. Alexopoulos, B. Behrouzian, B. Dawson, B. Black, J. Chem. Soc. Perkin Trans. 1 1997, 2617-2624.
166. a) M. Schlosser, F. Mongin, J. Porwisiak, W. Dmowski, H. H. Büker, N. M. M. Nibbering, Chem. Eur. J. 1998, 4, 1281-1286;
167. b) E. Marzi, F. Mongin, A. Spitaleri, M. Schlosser, Eur. J. Org. Chem. 2001, 2911-2915.
168. M. Schlosser, J. Gorecka, E. Castagnetti, Eur. J. Org. Chem. 2003, 452-562.
169. F. Faigl, M. Schlosser, Tetrahedron Lett. 1991, 32, 3369-3370.
170. M. Schlosser, G.-f. Zhong, Tetrahedron Lett. 1993, 34, 5441-5444.