New trends in the chemistry of α-fluorinated ethers, thioethers, amines and phosphines

Journal of Fluorine Chemistry

Volumn 131, Issue 2, 2010, Pages 140-158

  Manteau, Baptiste ^a   Pazenok, Sergiy ^b   Vors, Jean Pierre ^c   Leroux, Frédéric R ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

^b BAYER CROPSCIENCE AG   (Germany)

^c BAYER AG   (Germany)

Author keywords

Agrochemistry; Amines; Difluoromethyl; Ethers; Fluorination; Fluoromethyl; Pharmaceutical chemistry; Phosphines; Thioethers; Trifluoromethyl

Indexed keywords

EID: 74449085744     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2009.09.009     Document Type: Review

References (164)

1. Hammond G.B. At the Millenium ACS National Meeting. San Francisco, March 26-30 (2000)
2. Muller K., Faeh C., and Diederich F. Science 317 (2007) 1881
3. Banks R.E., Smart B.E., and Tatlow J.C. Organofluorine Chemistry: Principles and Commercial Applications (1994), Plenum Press, New York
4. British Crop Protection Council. The e-Pesticide Manual. A World Compendium, Version 3.2. 13 ed. (2005-2006), British Crop Protection Council
5. Harder H.H., Riley S.L., McCann S.F., and Irving S.N. British Crop Prot. Conf. Pest Dis. 2 (1996) 449
6. Sheets J.J. In: Krämer W., and Schirmer U. (Eds). Modern Crop Protection Compounds (2007), Wiley-VCH, Weinheim 813
7. R.L. Benefiel, E.V. Krumkalns, US 4002628 (to Elli Lilly and Co.), 1977.
8. O'Reilly P., Kobayashi S., Yamane S., Phillips W., Raymond P., and Castanho B. Brighton Crop Prot. Conf. Pest Dis. 1 (1992) 427
9. Santel H.J., Bowden B.A., Sorensen V.M., and Müller K.H. British Crop Prot. Conf. Pest Dis. 1 (1999) 23
10. Whitney W.K., and Wettstein K. British Crop Prot. Conf. Pest Dis. 2 (1979) 387
11. Garavaglia C., Mirenna L., Puppin O., and Spagni E. Brighton Crop Prot. Conf. Pest Dis. 1 (1988) 49
12. Gehmann K., Nyfeler R., Leadbeater A.J., Nevill D., and Sozzi D. Brighton Crop Prot. Conf. Pest Dis. 2 (1990) 399
13. Maurer W., Gerber H.R., and Rufener J. Proc. - British Crop Prot. Conf. - Weeds 1 (1987) 41
14. Colliot F., Kukorowski K.A., Hawkins D.W., and Roberts D.A. Brighton Crop Prot. Conf. Pest Dis. 1 (1992) 29
15. Hamon N., Shaw R., and Yang H. Proc. Beltwide Cotton Conf. 2 (1996) 759
16. Leroux F., Jeschke P., and Schlosser M. Chem. Rev. 105 (2005) 827
17. Jeschke P., Baston E., and Leroux F.R. Mini-Rev. Med. Chem. 7 (2007) 1027
18. Vitolina R., and Latvijas P.S.R. Zinatnu Akad Vestis 6 (1987) 75
19. Quagliato D.A., Humber L.G., Joslyn B.L., Soll R.M., Browne E.N.C., Shaw C., and Van Engen D. Bioorg. Med. Chem. Lett. 1 (1991) 39
20. Reid P. Current Opinion in Investigational Drugs 3 (2002), Pharma Press Ltd. p. 1165
21. Yamazaki N., Atobe M., and Kibayashi C. Tetrahedron Lett. 43 (2002) 7979
22. Rosen T.J., Coffman K.J., McLean S., Crawford R.T., Bryce D.K., Gohda Y., Tsuchiya M., Nagahisa A., Nakane M., and Lowe J.A. Bioorg. Med. Chem. Lett. 8 (1998) 281
23. Obach R.S., Maroolis J.M., and Logman M.J. Drug Metab. Pharmacokinet. 22 (2007) 336
24. Jimonet P., Audiau F., Barreau M., Blanchard J.-C., Boireau A., Bour Y., Coleno M.-A., Doble A., Doerflinger G., Do Huu C., Donat M.-H., Duchesne J.M., Ganil P., Gueremy C., Honore E., Just B., Kerphirique R., Gontier S., Hubert P., Laduron P.M., Le Blevec J., Meunier M., Miquet J.-M., Nemecek C., Pasquet M., Piot O., Pratt J., Rataud J., Reibaud M., Stutzmann J.-M., and Mignani S. J. Med. Chem. 42 (1999) 2828
25. Kromer W. Curr. Top. Pharmacol. 5 (2000) 45
26. Badwan A.A., Nabulsi L.N., Al Omari M.M., Daraghmeh N.H., Ashour M.K., Abdoh A.M., and Jaber A.M.Y. Anal. Profiles Drug Subst. Excipients 29 (2002) 213
27. Cheer S.M., Prakash A., Faulds D., and Diana H.M. Drugs 63 (2003) 101
28. Curtis-Prior P.B., and Prouteau M. Int. J. Obesity 7 (1983) 575
29. Page G.O. Synth. Commun. 23 (1993) 765
30. Sharpe T.R., Cherkovsky S.C., Hewes W.E., Smith D.H., Gregory W.A., Haber S.B., Leadbetter M.R., and Whitney J.G. J. Med. Chem. 28 (1985) 1188
31. Swingle K.F., Harrington J.K., Hamilton R.R., and Kvam D.C. Arch. Int. Pharmacodyn. Ther. 192 (1971) 16
32. Matsubara T. Drug Metab. Pharmacokinet. 17 (2002) 379
33. Yokoyama K., Yamanouchi K., and Ohyanagi H. Zairyo Gijutsu 2 (1984) 632
34. In: Begué J.-P., and Bonnet-Delpon D. (Eds). Bioorganic and Medicinal Chemistry of Fluorine (2008), John Wiley & Sons, Inc.
35. Bégué J.-P., and Bonnet-Delpon D. J. Fluorine Chem. 127 (2006) 992
36. Olah G.A., Yamato T., Hashimoto T., Shih J.G., Trivedi N., Singh B.P., Piteau M., and Olah J.A. J. Am. Chem. Soc. 109 (1987) 3708
37. Sheppard W.A. J. Am. Chem. Soc. 85 (1963) 1314
38. Haas A. Adv. Inorg. Chem. Radio Chem. 28 (1984) 167
39. Hansch C., and Leo A. Substituent Constants for Correlation Analysis in Chemistry and Biology (1979), John Wiley and Sons, New York
40. Leo A., Jow P.Y.C., Silipo C., and Hansch C. J. Med. Chem. 18 (1975) 865
41. Boehm H.-J., Banner D., Bendels S., Kansy M., Kuhn B., Mueller K., Obst-Sander U., and Stahl M. Chembiochem 5 (2004) 637
42. Leroux F.R., Manteau B., Vors J.-P., and Pazenok S. Beilstein J. Org. Chem. 4 (2008) 13
43. Ringom R., and Benneche T. Acta Chem. Scand. 53 (1999) 41
44. Mason C.T., and Allain C.C. J. Am. Chem. Soc. 78 (1956) 1682
45. Hudlicky M. Org. React. 35 (1988) 539
46. McCarthy J.R., Peet N.P., LeTourneau M.E., and Inbasekaran M. J. Am. Chem. Soc. 107 (1985) 735
47. Prakash G.K.S., Ledneczki I., Chacko S., and Olah G.A. Org. Lett. 10 (2008) 557
48. Zhang W., Zhu L., and Hu J. Tetrahedron 63 (2007) 10569
49. Zhang M.-R., Maeda J., Furutsuka K., Yoshida Y., Ogawa M., Suhara T., and Suzuki K. Bioorg. Med. Chem. Lett. 13 (2003) 201
50. Zhang M.-R., Maeda J., Ito T., Okauchi T., Ogawa M., Noguchi J., Suhara T., Halldin C., and Suzuki K. Bioorg. Med. Chem. 13 (2005) 1811
51. Zhang M.-R., Ogawa M., Furutsuka K., Yoshida Y., and Suzuki K. J. Fluorine Chem. 125 (2004) 1879
52. Lesuisse D., Gourvest J.F., Hartmann C., Tric B., Benslimane O., Philibert D., and Vevert J.P. J. Med. Chem. 35 (1992) 1588
53. Kanai T., Kai Y., Sato N., Naito T., Kamiya T., Nakamura T., and Ogura K. Bull. Chem. Soc. Jpn. 66 (1993) 2335
54. Gerus I.I., Kolomeitsev A.A., Kolycheva M.I., and Kukhar V.P. J. Fluorine Chem. 105 (2000) 31
55. Iwata R., Pascali C., Bogni A., Furumoto S., Terasaki K., and Yanai K. Appl. Radiat. Isot. 57 (2002) 347
56. Hamill T.G., McCauley J.A., and Burns H.D. J. Labelled Compd. Radiopharm. 48 (2005) 1
57. Donohue S.R., Halldin C., and Pike V.W. Bioorg. Med. Chem. Lett. 14 (2006) 3712
58. Chin F.T., Morse C.L., Shetty H.U., and Pike V.W. J. Labelled Compd. Radiopharm. 49 (2006) 17
59. Rheude U., and Sundermeyer W. Chem. Ber. 118 (1985) 2208
60. Grozinger K.G., Kriwacki R.W., Leonard S.F., and Pitner T.P. J. Org. Chem. 58 (1993) 709
61. Gao M., Miller M.A., DeGrado T.R., Mock B.H., Lopshire J.C., Rosenberger J.G., Dusa C., Das M.K., Groh W.J., Zipes D.P., Hutchins G.D., and Zheng Q.-H. Bioorg. Med. Chem. Lett. 15 (2007) 1289
62. Iwata R., Furumoto S., Pascali C., Bogni A., and Ishiwata K. J. Labelled Compd. Radiopharm. 46 (2003) 555
63. Stavber S., and Zupan M. Tetrahedron Lett. 34 (1993) 4355
64. Lu Q., and Benneche T. Acta Chem. Scand. 50 (1996) 850
65. Patrick T.B., Johri K.K., White D.H., Bertrand W.S., Mokhtar R., Kilbourn M.R., and Welch M.J. Can. J. Chem. 64 (1986) 138
66. Patrick T.B., Johri K.K., and White D.H. J. Org. Chem. 48 (1983) 4158
67. Ochiai M., Yoshimura A., Mori T., Nishi Y., and Hirobe M. J. Am. Chem. Soc. 130 (2008) 3742
68. Fuchigami T., Konno A., Nakagawa K., and Shimojo M. J. Org. Chem. 59 (2002) 5937
69. Reutrakul V., and Pohmakotr M. e-EROS Encycl. Reagents Org. Synth. (2001)
70. Umemoto T., and Tomizawa G. Bull. Chem. Soc. Jpn. 59 (1986) 3625
71. Robins M.J., and Wnuk S.F. J. Org. Chem. 58 (1993) 3800
72. McCarthy J.R., Matthews D.P., and Paolini J.P. Org. Synth. 72 (1995) 209
73. Singh R.P., and Shreeve J.n.M. Synthesis (2002) 2561
74. Wnuk S.F., and Robins M.J. J. Org. Chem. 55 (1990) 4757
75. Lal G.S., Pez G.P., Pesaresi R.J., Prozonic F.M., and Cheng H. J. Org. Chem. 64 (1999) 7048
76. Furuta S., Kuroboshi M., and Hiyama T. Bull. Chem. Soc. Jpn. 71 (1998) 2687
77. Lal G.S. J. Org. Chem. 58 (2002) 2791
78. Ayuba S., Yoneda N., Fukuhara T., and Hara S. Bull. Chem. Soc. Jpn. 75 (2002) 1597
79. Ayuba S., Fukuhara T., and Hara S. Org. Lett. 5 (2003) 2873
80. Ayuba S., Hiramatsu C., Fukuhara T., and Hara S. Tetrahedron 60 (2004) 11445
81. Cox D.G., and Burton D.J. J. Org. Chem. 53 (1988) 366
82. Burton D.J., and Wiemers D.M. J. Fluorine Chem. 27 (1985) 85
83. Langlois B.R. J. Fluorine Chem. 41 (1988) 247
84. Clark R.F., and Simons J.H. J. Am. Chem. Soc. 77 (1955) 6618
85. Miller T.G., and Thanassi J.W. J. Org. Chem. 25 (1960) 2009
86. Kuroboshi M., and Hiyama T. Synlett (1994) 251
87. Haas A., Spitzer M., and Lieb M. Chem. Ber. 121 (1988) 1329
88. Pasenok S.V., Yagupolskii Y.L., Tyrra W., and Naumann D. Z. Anorg. Allg. Chem. 625 (1999) 831
89. Tyrra W., and Naumann D. J. Prakt. Chem. -Chem. -Ztg. 338 (1996) 283
90. Naumann D., Moeckel R., and Tyrra W. Angew. Chem. Int. Ed. 33 (1994) 323
91. Moeckel R., Tyrra W., and Naumann D. J. Fluorine Chem. 73 (1995) 229
92. Miethchen R., Hein M., Naumann D., and Tyrra W. Liebigs Ann. (1995) 1717
93. Lal G.S., Lobach E., and Evans A. J. Org. Chem. 65 (2000) 4830
94. Yagupolskii L.M., and Troitskaya V.I. J. Gen. Chem. USSR (Engl. Transl.) 30 (1960) 3102
95. Yagupolskii L.M., and Troitskaya V.I. J. Gen. Chem. USSR (Engl. Transl.) 31 (1961) 845
96. Stogryn E.L. J. Org. Chem. 37 (1972) 673
97. Dallacker F., and Zegers H. Liebigs Ann. Chem. 689 (1965) 156
98. Yagupolskii L.M., and Belinskaya R.V. Zh. Obshch. Khim. 33 (1963) 2358
99. N. Lui, A. Marhold, K.-R. Gassen, EP 623609 (to Bayer AG), 1994.
100. Dmowski W., and Wielgat J. J. Fluorine Chem. 37 (1987) 429
101. Zhang L., Zheng J., and Hu J. J. Org. Chem. 71 (2006) 9845
102. Zheng J., Li Y., Zhang L., Hu J., Meuzelaar G.J., and Federsel H.-J. Chem. Commun. (2007) 5149
103. Zhang W., Zhu J., and Hu J. Tetrahedron Lett. 49 (2008) 5006
104. Yagupolskii L.M., Petko K.I., Retchitsky A.N., and Maletina I.I. J. Fluorine Chem. 76 (1996) 95
105. Arnold Z. Coll. Czech. Chem. Commun. 28 (1963) 2047
106. W. Ebenbeck, P. Hilgers, A. Marhold, J.A. Barten, A. Kolomeitsev, G.-V. Roeschenthaler, EP 1437342 (to Bayer Chemicals AG, Germany), 2004.
107. Petko K.I., and Tolmachev A.A. Russ. J. Org. Chem. (Translation of Zhur. Org. Khimii) 38 (2002) 1030
108. Yarovenko N.N., and Raksha M.A. Zh. Obshch. Khim. 29 (1959) 2159
109. Takaoka A., Iwakiri H., and Ishikawa N. Bull. Chem. Soc. Jpn. 51 (1978) 1267
110. Petrov V.A., Swearingen S., Hong W., and Chris Petersen W. J. Fluorine Chem. 109 (2001) 25
111. Hayashi H., Sonoda H., Fukumura K., and Nagata T. Chem. Commun. (2002) 1618
112. Pasenok S.V., Kirij N.V., Yagupolskii Y.L., Naumann D., Tyrra W., and Fitzner A. Z. Anorg. Allg. Chem. 625 (1999) 834
113. Prakash G.K.S., Weber C., Chacko S., and Olah G.A. Org. Lett. 9 (2007) 1863
114. Abrunhosa-Thomas I., Sellers C.E., and Montchamp J.-L. J. Org. Chem. 72 (2007) 2851
115. Fild M., Jones P.G., and Ruhnau K. J. Fluorine Chem. 54 (1991) 387
116. Clarke M.L., Guy Orpen A., Pringle P.G., and Turley E. Dalton Trans. (2003) 4393
117. Kirij N.V., Pasenok S.V., Yagupolskii Y.L., Fitzner A., Tyrra W., and Naumann D. J. Fluorine Chem. 94 (1999) 207
118. Yagupol'skii L.M. Dokl. Akad. Nauk SSSR 105 (1955) 100
119. Yarovenko N.N., and Vasil'eva A.S. Zh. Obshch. Khim. 28 (1958) 2502
120. Yagupol'skii L.M. O.V.V., Zh. Obshch. Khim. 34 (1964) 1979
121. Yagupol'skii L.M., and Troitskaya V.I. Zh. Obshch. Khim. 31 (1961) 915
122. Louw R., and Franken P.W. Chem. Ind. (1977) 127
123. Feiring A.E. J. Org. Chem. 44 (1979) 2907
124. Sheppard W.A. J. Org. Chem. 29 (1964) 1
125. Kuroboshi M., Suzuki K., and Hiyama T. Tetrahedron Lett. 33 (1992) 4173
126. Kanie K., Tanaka Y., Suzuki K., Kuroboshi M., and Hiyama T. Bull. Chem. Soc. Jpn. 73 (2000) 471
127. Kuroboshi M., Kanie K., and Hiyama T. Adv. Synth. Catal. 343 (2001) 235
128. Shimizu M., and Hiyama T. Angew. Chem. Int. Ed. 44 (2005) 214
129. Kanie K., Tanaka Y., Shimizu M., Kuroboshi M., and Hiyama T. Chem. Commun. (1997) 309
130. Umemoto T., and Ishihara S. J. Am. Chem. Soc. 115 (1993) 2156
131. Umemoto T., and Ishihara S. Tetrahedron Lett. 31 (1990) 3579
132. Umemoto T., Adachi K., and Ishihara S. J. Org. Chem. 72 (2007) 6905
133. Umemoto T., and Adachi K. J. Org. Chem. 59 (1994) 5692
134. Yagupol'skii L.M., Kondratenko N.V., and Timofeeva G.N. Zh. Org. Khim. 20 (1984) 115
135. Aldrich P.E., and Sheppard W.A. J. Org. Chem. 29 (1964) 11
136. Umemoto T. Chem. Rev. 96 (1996) 1757
137. Rozen S. Chem. Rev. 96 (1996) 1717
138. Eisenberger P., Gischig S., and Togni A. Chem. Eur. J. 12 (2006) 2579
139. Kieltsch I., Eisenberger P., and Togni A. Angew. Chem. Int. Ed. 46 (2007) 754
140. Eisenberger P., Kieltsch I., Armanino N., and Togni A. Chem. Commun. (2008) 1575
141. Stanek K., Koller R., and Togni A. J. Org. Chem. 73 (2008) 7678
142. Koller R., Stanek K., Stolz D., Aardoom R., Niedermann K., and Togni A. Angew. Chem. Int. Ed. 48 (2009) 4332
143. Trainor G.L. J. Carbohydr. Chem. 4 (1985) 545
144. Farnham W.B., Smart B.E., Middleton W.J., Calabrese J.C., and Dixon D.A. J. Am. Chem. Soc. 107 (1985) 4565
145. Kolomeitsev A.A., Vorobyev M., and Gillandt H. Tetrahedron Lett. 49 (2008) 449
146. Boiko V.N., Shchupak G.M., and Yagupolskii L.M. J. Org. Chem., USSR 13 (1977) 972
147. Wakselman C., and Tordeux M. J. Org. Chem. 50 (1985) 4047
148. Billard T., and Langlois B.R. Tetrahedron Lett. 37 (1996) 6865
149. Quiclet-Sire B., Saicic R.N., and Zard S.Z. Tetrahedron Lett. 37 (1996) 9057
150. Roques N. J. Fluorine Chem. 107 (2001) 311
151. Blond G., Billard T., and Langlois B.R. Tetrahedron Lett. 42 (2001) 2473
152. Chan Q.-Y., and Duan J.-X. J. Chem. Soc., Chem. Commun. (1993) 918
153. Tyrra W., Naumann D., Hoge B., and Yagupolskii Y.L. J. Fluorine Chem. 119 (2003) 101
154. Billard T., Roques N., and Langlois B.R. J. Org. Chem. 64 (1999) 3813
155. Langlois B.R., Billard T., Mulatier J.-C., and Yezeguelian C. J. Fluorine Chem. 128 (2007) 851
156. Pooput C., Medebielle M., and Dolbier W.R. Org. Lett. 6 (2004) 301
157. Pooput C., Dolbier W.R., and Medebielle M. J. Org. Chem. 71 (2006) 3564
158. Yagupolskii L.M., Kondratenko N.V., Timofeeva G.N., Dronkina M.I., and Yagupolskii Y.L. Zh. Org. Khim. 16 (1980) 2508
159. Harder R.J., and Smith W.C. J. Am. Chem. Soc. 83 (1961) 3422
160. Dmowski W., and Kaminski M. J. Fluorine Chem. 23 (1983) 207
161. Dronkina M.I., Petko K.I., Turra V., and Yagupol'skii L.M. Ukr. Khimi. Zhur. (Russian Edition) 68 (2002) 100
162. Klauke E. Angew. Chem. Int. Ed. Engl. 5 (1966) 848
163. Pawelke G. J. Fluorine Chem. 52 (1991) 229
164. Schlosser M. Angew. Chem. Int. Ed. 37 (1998) 1496