Functionalized fluoroalkyl and alkenyl silanes: Preparations, reactions, and synthetic applications

Journal of Fluorine Chemistry

Volumn 129, Issue 7, 2008, Pages 550-576

  Uneyama, Kenji ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

1 Substituted 2,2 difluorovinylsilanes; 1 Substituted difluoromethylsilanes; C single bond F bond activation; Defluorination; Desilylation; Fluoroalkenylsilane; Fluoroalkylsilane; Trifluoroacetimidoylsilane; Trifluoroacetylsilane; Trifluoroisopropenylsilane

Indexed keywords

EID: 46749086559     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2008.05.012     Document Type: Review

References (170)

1. Miura K., and Hosomi A. In: Yamamoto H., and Oshima K. (Eds). Main Group Metals in Organic Synthesis (2004), Wiley-VCH
2. Fleming I. In: Jones D.N. (Ed). Comprehensive Organic Chemistry vol. 3 (1979), Pergamon Press, Oxford
3. In: Rappoport Z., and Apeloig Y. (Eds). The Chemistry of Organo Silicon Compounds vol. 2 (1998), Wiley, Chichester
4. Langkopf E., and Schinzer D. Chem Rev. 95 (1995) 1375-1408
5. Fleming I., Barbero A., and Walter D. Chem. Rev. 97 (1997) 2063-2197
6. Prakash G.K.S., and Yudin A.K. Chem. Rev. 97 (1997) 757-786
7. Singh R.P., and Shreeve J.M. Tetrahedron 56 (2000) 7613-7632
8. Fuchikami T., and Ojima I. J. Organomet. Chem. 212 (1981) 145-153
9. Gilman H. J. Organomet. Chem. 100 (1975) 83
10. Yudin A.K., Prakash G.K.S., Deffieux D., Bradley M., Bau R., and Olah G.A. J. Am. Chem. Soc. 119 (1997) 1572-1581
11. 3TMS and TMS, hereafter.
12. Martynov B.I., and Stepanov A.A. J. Fluorine Chem. 85 (1997) 127-128
13. Uneyama K. Organofluorine Chemistry (2006), Blackwell Publishing, Oxford, UK
14. Prakash G.K.S., and Hu J. Acc. Chem. Res. 40 (2007) 921-930
15. Prakash G.K.S., Hu J., and Olah G.A. J. Org. Chem. 68 (2003) 4457-4463
16. Toulgoat F., Langlois B.R., Medebielle M., and Sanchez J.-Y. J. Org. Chem. 72 (2007) 9046-9052
17. Prakash G.K.S., Hu J., Wang Y., and Olah G.A. J. Fluorine Chem. 126 (2005) 529-534
18. Pohmakotr M., Boonkitpattarakul K., Ieawsuwan W., Jarussophon S., Duangdee N., Tuchinda P., and Reutrakul V. Tetrahedron 62 (2006) 5973-5985
19. Pohmakotr M., Panichakul D., Tuchinda P., and Reutrakul V. Tetrahedron 63 (2007) 9429-9436
20. Li Y., and Hu J. Angew. Chem. Int. Ed. 46 (2007) 2489-2492
21. Mizuta S., Shibata N., Ogawa S., Fujimoto H., Nakamura S., and Toru T. Chem. Commun. (2006) 2575-2577
22. Hagiwara T., and Fuchikami T. Synlett (1995) 717-718
23. Prakash G.K.S., Hu J., Wang Y., and Olah G.A. Eur. J. Org. Chem. (2005) 2218-2223
24. Ni C., and Hu J. Tetrahedron Lett. 46 (2005) 8273-8277
25. Fujii A., Usuki Y., Iio H., and Tokoroyama T. Synlett (1994) 725-726
26. Asakura N., Usuki Y., and Iio H. J. Fluorine Chem. 124 (2003) 81-88
27. Qin Y.-Y., Qiu X.-L., Yang Y.-Y., Meng W.-D., and Qing F.-L. J. Org. Chem. 70 (2005) 9040-9043
28. Sugimoto H., Nakamura S., Shibata Y., Shibata N., and Toru T. Tetrahedron Lett. 47 (2006) 1337-1340
29. for phenoxy 77. Guidotti J., Metz F., Tordeux M., and Wakselman C. Synlett (2004) 1759-1762
30. for phenoxy 79. Bissky G., Staninets V.I., Kolomeitsev A.A., and Roschenthaler G.-V. Synlett (2001) 374-378
31. Patel N.R., Chen J., Kirchmeier R.L., and Shreeve J.M. Inorg. Chem. 34 (1995) 13-17
32. Burton D.J., Takei R., and Shinya S. J. Fluorine Chem. 18 (1981) 197-202 (Generation of cadmium reagent and its reaction with electrophiles were described)
33. Obayashi M., Ito E., Matsui K., and Kondo K. Tetrahedron Lett. 23 (1982) 2323-2326
34. Nieschalk J., and O'Hagan D. J. Chem. Soc., Chem. Commun. (1995) 719-720
35. Waschbusch R., Samadi M., and Savignac P. J. Organomet. Chem. 529 (1997) 267-278
36. Adams L.A., Charmant J.P.H., Cox R.J., Walter M., and Whittingham W.G. Org. Biomol. Chem. 2 (2004) 542-553
37. Obayashi M., and Kondo K. Tetrahedron Lett. 23 (1982) 2327-2328
38. Cox R.J., Hadfield A.T., and Mayo-Martin M.B. Chem. Commun. (2001) 1710-1711
39. Cox R.J., Gibson J.S., and Martin M.B.M. ChemBioChem 3 (2002) 874-886
40. Reily M.D., Robosky L.C., Manning M.L., Butler A., Baker J.D., and Winters R.T. J. Am. Chem. Soc. 128 (2006) 12360-12361
41. Uneyama K., and Mizutani G. Chem. Commun. (1999) 613-614
42. Stepanov A.A., Minyaeva T.V., and Martinov B.I. Tetrahedron Lett. 40 (1999) 2203-2204
43. Bordeau M., Clavel P., Barba A., Berlande M., Biran C., and Roques N. Tetrahedron Lett. 44 (2003) 3741-3744
44. Clavel P., Biran C., Bordeau M., Roques N., and Trevin S. Tetrahedron Lett. 41 (2000) 8763-8767
45. Amii H., Kobayashi T., and Uneyama K. Synthesis (2000) 2001-2003
46. Bordeau M., Frébault F., Gobet M., and Picard J.-P. Eur. J. Org. Chem. (2006) 4147-4154
47. Uneyama K., Mizutani G., Maeda K., and Kato T. J. Org. Chem. 64 (1999) 6717-6723
48. Yoshida M., Suzuki D., and Iyoda M. Chem. Lett. (1994) 2357-2360
49. Yoshida M., Suzuki D., and Iyoda M. J. Chem. Soc. Perkin Trans. 1: Org. Bio-Org. Chem. (1997) 643-648
50. Clavel P., Leger-Lambert M.-P., Biran C., Serein-Spirau F., Bordeau M., Roques N., and Marzouk H. Synthesis (1999) 829-834
51. Clavel P., Lessene G., Biran C., Bordeau M., Roques N., Trevin S., and de Montauzon D. J. Fluorine Chem. 107 (2001) 301-310
52. Kako M., Morita T., Torihara T., and Nakadaira Y. J. Chem. Soc., Chem. Commun. (1993) 678-680
53. Amii H., Hatamoto Y., Seo M., and Uneyama K. J. Org. Chem. 66 (2001) 7216-7618
54. Moore J.A., and Lang C.-I.C. In: Hougham G., Cassidy P.E., Johns K., and Davidson T. (Eds). Fluoropolymers 1: Synthesis (1999), Plenum Press, New York 273-312
55. Dolbier Jr. W.R., Duan J.-X., and Roche A.J. Org. Lett. 2 (2000) 1867-1869
56. Dolbier Jr. W.R., and Beach W.F. J. Fluorine Chem. 122 (2003) 97-109 (and references cited therein)
57. Kawano Y., Kaneko N., and Mukaiyama T. Bull. Chem. Soc. Jpn. 79 (2006) 1133-1145
58. Mogi R., Morisaki K., Hu J., Prakash S.G.K., and Olah G.A. J. Fluorine Chem. 128 (2007) 1098-1103
59. Barker S.A., Haszeldine R.N., and Robinson P.J. J. Chem. Soc., Perkin Trans. 2 (1987) 1861-1865
60. Solladié-Cavallo A., and Suffert J. Synthesis (1985) 659-662
61. Fuhrmann U., Hess-Stumpp H., Cleve A., Neef G., Schwede W., Hoffmann J., Fritzemeier K.-H., and Chwalisz K. J. Med. Chem. 43 (2000) 5010-5016
62. K. Uneyama, T. Katagiri, H. Amii, Acc. Chem. Res. (2008), doi:10.1021/ar7002573, in press.
63. Chemistry of perfluoroalkyl(trialkyl)silanes, see Ref. [2].
64. Atherton J.H., and Fields R. J. Chem. Soc. (C) (1968) 2276-2278 Photolysis of 2,2,2-trifluorodiazoethane in the presence of ten-molar excess of trimethylsilane at 25 °C gave 2,2,2-trifluoroethyltrimethylsilane in 34% yield along with 3,3,3-trifluoropropyl(dimethyl)silane (41%). No reaction of 2,2,2-trifluoroethyltrimethylsilane has been reported
65. Watanabe S., Fujita M., Sakamoto M., Mino Y., and Kitazume T. J. Fluorine Chem. 73 (1995) 21-26
66. Hoffmann-Röder A., Schweizer E., Egger J., Seiler P., Obst-Sander U., Wagner B., Kansy M., Banner D.W., and Diederich F. Chem. Med. Chem. 1 (2006) 1205-1215
67. Urata H., and Fuchikami T. Tetrahedron Lett. 32 (1991) 91-92
68. Yamashita Y., Ishitani H., Shimizu H., and Kobayashi S. J. Am. Chem. Soc. 124 (2002) 3292-3302
69. Singh R.P., and Shreeve J.M. Chem. Commun. (2002) 1818-1819
70. Yagupolskii Y.L., Kirij N.V., Shevchenko A.V., Tyrra W., and Naumann D. Tetrahedron Lett. 43 (2002) 3029-3031
71. Babadzhanova L.A., Kirij N.V., and Yagupolskii Y.L. J. Fluorine Chem. 125 (2004) 1095-1098
72. Grellepois F., Timoshenko V.M., Shermolovich Y.G., and Portella C. Org. Lett. 8 (2006) 4323-4326
73. Murphy-Jolly M.B., Lewis L.C., and Caffyn A.J.M. Chem. Commun. (2005) 4479-4480
74. Kolomeitsev A.A., Kadyrov A.A., Szczepkowska-Sztolcman J., Milewska M., Koroniak H., Bissky G., Barten J.A., and Roeschenthaler G.-V. Tetrahedron Lett. 44 (2003) 8273-8277
75. Seyferth D., and Wursthorn K.R. J. Organomet. Chem. 182 (1979) 455-464
76. Seyferth D., Simon R.M., Sepelak D.J., and Klein H.A. J. Org. Chem. 45 (1980) 2273-2274
77. Fujita M., and Hiyama T. J. Am. Chem. Soc. 107 (1985) 4085-4087
78. Rajaonah M., Rock M.H., Begue J.-P., Bonnet-Delpon D., Condon S., and Nedelec J.-Y. Tetrahedron Lett. 39 (1998) 3137-3140
79. Mae M., Hong J.A., Hammond G.B., and Uneyama K. Tetrahedron Lett. 46 (2005) 1787-1789
80. Martin S., Sauvetre R., and Normant J.-F. J. Organomet. Chem. 264 (1984) 155-161
81. Jairaj V., and Burton D.J. J. Fluorine Chem. 121 (2003) 75-77
82. Martynov B.I., Stepanov A.A., and Griffiths D.V. Tetrahedron 54 (1998) 257-262
83. Uneyama K. J. Fluorine Chem. 128 (2007) 1087-1090
84. Fujita M., Okabayashi M., and Hiyama T. Tetrahedron 44 (1988) 4135-4145
85. Seyferth D., Welch D.E., and Raab G. J. Am. Chem. Soc. 84 (1962) 4266-4269
86. Tarrant P., Johncock P., and Savory J. J. Org. Chem. 28 (1963) 839-843
87. Sauvetre R., Masure D., Chuit C., and Normant J.F. Syntheses (1978) 128-130
88. Liu Q., and Burton D.J. Org. Lett. 4 (2002) 1483-1485
89. Kvicala J., Hrabal J., Czernek J., Bartosova I., Paleta O., and Pelter A. J. Fluorine Chem. 113 (2002) 211-218
90. Kumamoto H., Onuma S., and Tanaka H. J. Org. Chem. 69 (2004) 72-78
91. Tellier F., Audouin M., Baudry M., and Sauvetre R. Tetrahedron Lett. 39 (1998) 5041-5044
92. Tellier F., Audouin M., Baudry M., and Sauvetre R. J. Fluorine Chem. 94 (1999) 27-36
93. Holfter H., Kirchmeier R.L., and Shreeve J.M. Inorg. Chem. 33 (1994) 6369-6372
94. Hass D., Holfter H., and Schroeder U. J. Fluorine Chem. 69 (1994) 89-95
95. Hiyama T., Nishide K., and Obayashi M. Chem. Lett. 13 (1984) 1756-1765
96. Okano T., Ito K., Ueda T., and Muramatsu H. J. Fluorine Chem. 32 (1986) 377-388
97. Bainbridge J.M., Brown S.J., Ewing P.N., Gibson R.R., and Percy J.M. J. Chem. Soc. Perkin Trans. 1 (1998) 2541-2546
98. Fujita M., Kondo K., and Hiyama T. Bull. Chem. Soc. Jpn. 60 (1987) 4385-4394
99. Martin S., Sauvetre R., and Normant J.-F. J. Organomet. Chem. 303 (1986) 317-320
100. Martin S., Sauvetre R., and Normant J.-F. J. Organomet. Chem. 367 (1989) 1-10
101. Fontana S.A., Davis C.R., He Y.-B., and Burton D.J. Tetrahedron 52 (1996) 37-44
102. Burton D.J., and Lu L. In: Chambers R.D. (Ed). Organofluorine Chemistry, Topics in Current Chemistry vol. 193 (1997), Springer, Berlin
103. Wang Y., Lu L., and Burton D.J. J. Org. Chem. 70 (2005) 10743-10746
104. Lim C., Burton D.J., and Wesolowski C.A. J. Fluorine Chem. 119 (2003) 21-26
105. Percy J.M. In: Chambers R.D. (Ed). Topics in Current Chemistry vol. 193 (1997), Springer, Berlin
106. J. Ichikawa, J. Synth. Org. Chem., 54 (1996) 654-664. CAN 125:194683.
107. J. Ichikawa, In: V.A. Soloshonok (Ed.), ACS Symposium Series 911(Fluorine-Containing Synthons), pp. 262-275, Oxford University Press/ACS, Washington DC, 2005.
108. Metcalf B.W., Jarvi E.T., and Burkhart J.P. Tetrahedron Lett. 26 (1985) 2684-2861
109. Garayt M.R., and Percy J.M. Tetrahedron Lett. 42 (2001) 6377-6380
110. Audouard C., Garayt M.R., Kerouredan E., Percy J.M., and Yang H. J. Fluorine Chem. 126 (2005) 611-623
111. Higashiya S., Chung W.J., Lim D.S., Ngo S.C., Kelly W.H., Toscano P.J., and Welch J.T. J. Org. Chem. 69 (2004) 6323-6328
112. Chung W., and Welch J.T. J. Fluorine Chem. 125 (2004) 543-548
113. Chung W.J., Ngo S.C., Higashiya S., and Welch J.T. Tetrahedron Lett. 45 (2004) 5403-5406
114. Amii H., Kobayashi T., Hatamoto Y., and Uneyama K. Chem. Commun. (1999) 1323-1324
115. Ngo S.C., Chung W.C., Lim D.S., Higashiya S., and Welch J.T. J. Fluorine Chem. 117 (2002) 207-211
116. Chung W.J., Omote M., and Welch J.T. J. Org. Chem. 70 (2005) 7784-7787
117. Bennett A.J., Percy J.M., and Rock M.H. Synlett (1992) 483-484
118. Lee J., Tsukazaki M., and Snieckus V. Tetrahedron Lett. 34 (1993) 415-418
119. Nakamura Y., and Uneyama K. J. Org. Chem. 72 (2007) 5894-5897
120. Ichikawa J., Ishibashi Y., and Fukui H. Tetrahedron Lett. 44 (2003) 707-710
121. Ichikawa J., Fukui H., and Ishibashi Y. J. Org. Chem. 68 (2003) 7800-7805
122. Petrov V.A., Mlsna T.E., and DesMarteau D.D. Mendeleev Commun. (1993) 240
123. Sauvetre R., and Normant J.-F. Tetrahedron Lett. 22 (1981) 957-958
124. Dubuffet T., Sauvetre R., and Normant J.-F. J. Organomet. Chem. 354 (1988) 1-6
125. Datta A.K., Fields R., and Haszeldine R.N. J. Chem. Res., Synopses (1980) 2-3
126. Mironov V.F., Rad'kova O.M., Sheludyakov V.D., and Shcherbinin V.V. Doki. Akad. Nauk SSSR 207 (1972) 114
127. Wheaton G.A., and Burton D.J. Tetrahedron Lett. 32 (1976) 895
128. Seyferth D., Wursthorn K.R., Lim T.F.O., and Sepelak D.J. J. Organomet. Chem. 205 (1981) 301-309
129. Gonzalez J., Foti M.J., and Elsheimer S. Org. Synth. 72 (1995) 225-231
130. Sauvetre R., and Normant J.F. Tetrahedron Lett. 22 (1981) 957-958
131. Tellier F., Baudry M., and Sauvetre R. Tetrahedron Lett. 38 (1997) 5989-5992
132. Shi G.Q., and Huang X.H. Tetrahedron Lett. 37 (1996) 5401-5404
133. Huang X.H., He P.Y., and Shi G.Q. J. Org. Chem. 65 (2000) 627-629
134. Drakesmith F.G., Stewart O.J., and Tarrant P. J. Org. Chem. 33 (1967) 280-289
135. Hanzawa Y., Kawagoe K., Kimura N., and Kobayashi Y. Chem. Pharm. Bull. 34 (1986) 3953-5395
136. Dolbier Jr. W.R., Burkholder C.R., and Piedrahita C.A. J. Fluorine Chem. 20 (1982) 637-647
137. Jiang B., Wang Q.-F., Yang C.-G., and Xu M. Tetrahedron Lett. 42 (2001) 4083-4085
138. A. Tanaka, A. Watanabe, K. Kawada, H. Kanezaki, WO 2006064628 A1 20060622, CAN 145:63035.
139. A. Tanaka, T. Sato, A. Watabe, K. Kawada, JP 2008007415 A 20080117, CAN 148:168380.
140. Ojima I., Fuchikami T., and Yatabe M. J. Organomet. Chem. 260 (1984) 335-346
141. Li Y., Lu L., and Zhao X. Org. Lett. 6 (2004) 4467-4470
142. Rayner C.M., Astles P.C., and Paquette L.A. J. Am. Chem. Soc. 114 (1992) 3926-3936
143. Hanamoto T., Anno R., Yamada K., and Ryu K. Tetrahedron Lett. 48 (2007) 3727-3730
144. Funabiki K., Ohtsuki T., Ishihara T., and Yamanaka H. J. Chem. Soc. Perkin Trans. 1 15 (1998) 2413-2424
145. Yoshimatsu M., and Kinoshita S. Chem. Pharm. Bull. 48 (2000) 145-147
146. Begue J.-P., and Rock M.H. J. Organomet. Chem. 489 (1995) 1-2
147. Brisdon A.K., Crossley I.R., Flower K.R., Pritchard R.G., Sadiq G., and Warren J.E. Organometallics 22 (2003) 5534-5542
148. Brisdon A.K., Crossley I.R., Flower K.R., Pritchard R.G., and Warren J.E. Angew. Chem. Int. Ed. 42 (2003) 2399-2401
149. Chae J., Konno T., Kanda M., Ishihara T., and Yamanaka H. J. Fluorine Chem. 120 (2003) 185-193
150. Seyferth D., Wursthorn K.R., Lim T.F.O., and Sepelak D.J. J. Organomet. Chem. 181 (1979) 293-304
151. Cullen W.R., and Leeder W.R. Inorg. Chem. 5 (1966) 1004-1008
152. Bogoradovskii E.T., Zavgorodnii V.S., Polozov B.V., and Petrov A.A. Zhurnal Obshchei Khimii 52 (1982) 455-456
153. Uneyama K., Amii H., Katagiri T., Kobayashi T., and Hosokawa T. J. Fluorine Chem. 126 (2005) 165-171
154. Watanabe H., Yamashita F., and Uneyama K. Tetrahedron Lett. 34 (1999) 1941-1944
155. Akamatsu C., Yamauchi Y., Kobayashi T., Ozeki Y., Takagi J., Amii H., and Uneyama K. Synthesis (2006) 1836-1840
156. Uneyama K., Noritake C., and Sadamune S. J. Org. Chem. 61 (1996) 6055-6057
157. Kobayashi T., Nakagawa T., Amii H., and Uneyama K. Org. Lett. 5 (2003) 4297-4300
158. Mae M., Amii H., and Uneyama K. Tetrahedron Lett. 41 (2000) 7893-7896
159. Amii H., Ichihara Y., Nakagawa T., Kobayashi T., and Uneyama K. Chem. Commun. (2003) 2902-2903
160. Jin F., Jiang B., and Xu Y. Tetrahedron Lett. 33 (1992) 1221-1224
161. Brook A.G. J. Am. Chem. Soc. 80 (1958) 1886-1889
162. Jin F., and Xu Y. J. Fluorine Chem. 52 (1993) 207-210
163. Bonini B.F., Comes-Franchini M., Fochi M., Mazzanti G., Nanni C., and Ricci A. Tetrahedron Lett. 39 (1998) 6737-6740
164. Jin F., Xu Y., and Huang W. J. Chem. Soc., Chem. Commun. (1993) 814-816
165. Jin F., Xu Y., and Huang W. J. Chem. Soc. Perkin Trans. 1 (1993) 795-799
166. Suda M. Tetrahedron Lett. 21 (1980) 4355-4358
167. Shibuya A., Pietz S., and Taguchi T. Tetrahedron Lett. 38 (1997) 5537-5540
168. Yamauchi Y., Katagiri T., and Uneyama K. Org. Lett. 4 (2002) 173-176
169. Yamauchi Y., Kawate T., Itahashi H., Katagiri T., and Uneyama K. Tetrahedron Lett. 44 (2003) 6319-6322
170. Yamauchi Y., Kawate T., Katagiri T., and Uneyama K. Tetrahedron 59 (2003) 9839-9847