Bi-functional fluoroalkylation reagents: An introduction to halo-substituted 3-oxa-perfluoroalkanesulfonyl fluorides

Tetrahedron

Volumn 69, Issue 51, 2013, Pages 10955-10989

  Zhang, Cheng Pan ^a   Chen, Qing Yun ^a   Guo, Yong ^a   Xiao, Ji Chang ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Addition; Fluorine; Functional; Perfluoroalkylation; Radical; Reagents

Indexed keywords

ALKANE; ALKENE; ALKYNE; ELECTROLYTE; FLUORIDE; ION EXCHANGE RESIN; ORGANIC COMPOUND; PERFLUORO COMPOUND; POLYCYCLIC AROMATIC HYDROCARBON; POLYMER; RADICAL; REDUCING AGENT; SULFONAMIDE; SULFONIC ACID DERIVATIVE; SURFACTANT;

AMIDATION; ARTICLE; CATALYST; CHEMICAL REACTION; CONTROLLED STUDY; ELECTRON TRANSPORT; ESTERIFICATION; FLUORINATION; FLUOROALKYLATION; HALOGENATION; HEAT; PRIORITY JOURNAL; SUBSTITUTION REACTION; ULTRAVIOLET RADIATION;

EID: 84888640371     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2013.10.058     Document Type: Article

References (262)

1. I. Ojima Fluorine in Medicinal Chemistry and Chemical Biology 2009 Wiley Chichester, UK
2. J.-P. Bégué, and D. Bonnet-Delphon Bioorganic and Medicinal Chemistry of Fluorine 2008 Wiley Hoboken, NJ
3. K. Uneyama Organofluorine Chemistry 2006 Blackwell Oxford, UK
4. P. Kirsch Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications 2004 Wiley-VCH Weinheim, Germany
5. R.D. Chambers Fluorine in Organic Chemistry 2004 Blackwell Oxford, UK
6. T. Hiyama Organofluorine Compounds: Chemistry and Applications 2000 Springer New York, NY
7. J.A. Gladysz, D.P. Curran, and I.T. Horváth Handbook of Fluorous Chemistry 2004 Wiley-VCH Weinheim, Germany
8. D. O'Hagan Chem. Soc. Rev. 37 2008 308 319
9. K. Muller, C. Faeh, and F. Diederich Science 317 2007 1881 1886
10. K. Mikami, Y. Itoh, and M. Yamanaka Chem. Rev. 104 2004 1 16
11. S. Purser, P.R. Moore, S. Swallow, and V. Gouverneur Chem. Soc. Rev. 37 2008 320 330
12. M. Schlosser Angew. Chem., Int. Ed. 45 2006 5432 5446
13. T. Furuya, A.S. Kamlet, and T. Ritter Nature 473 2011 470 477
14. K. Uneyama, T. Katagiri, and H. Amii Acc. Chem. Res. 41 2008 817 829
15. C.-P. Zhang, Q.-Y. Chen, Y. Guo, J.-C. Xiao, and Y.-C. Gu Chem. Soc. Rev. 41 2012 4536 4559
16. A. Studer Angew. Chem., Int. Ed. 51 2012 8950 8958
17. F. Leroux, P. Jeschke, and M. Schlosser Chem. Rev. 105 2005 827 856
18. J.-A. Ma, and D. Cahard Chem. Rev. 108 2008 PR1 PR43
19. O.A. Tomashenko, and V.V. Grushin Chem. Rev. 111 2011 4475 4521
20. A.J. Hickman, and M.S. Sanford Nature 484 2012 177 185
21. J. Hu, W. Zhang, and F. Wang Chem. Commun. 2009 7465 7478
22. H. Wang, and D.A. Vicic Synlett 24 2013 1887 1898
23. L. Pauling The Nature of the Chemical Bond and the Structure of Molecules and Crystals: An Introduction to Modern Structural Chemistry 1939 Cornell University Press Ithaca, NY
24. J. Schmedt auf der Günne, M. Mangstl, and F. Kraus Angew. Chem., Int. Ed. 51 2012 7847 7849
25. Shanghai Guangming Electroplating Factory Huaxue Xuebao 35 1977 209 220
26. Perfluoro Sulfonic Acid Group, Shanghai Institute of Organic Chemistry Sci. Sin. 21 1978 773 782
27. Shanghai Institute of Organic Chemistry Huaxue Xuebao 37 1979 315 324
28. G.A. Bargigia, G. Caporiccio, and M. Pianca J. Fluorine Chem. 19 1982 403 410
29. C.-Y. Guo, Y.-F. Zhang, and Q.-Y. Chen Huaxue Xuebao 40 1982 828 834
30. Z. Zhang, J. Lu, P. Song, C. Xu, and N. Chen Huaxue Shijie 31 1990 272 275
31. C. Xu, Z. Zhang, and J.Y. Lu Yingyong Kexue Xuebao 9 1991 323 328
32. Q.-Y. Chen J. Fluorine Chem. 72 1995 241 246
33. Zhang, C. -P.; Chen, Q. -Y.; Guo, Y.; Gu, Y. -C.; Xiao, J. -C. 2013, submitted for publication.
34. B.-N. Huang, W.-Y. Huang, and C.-M. Hu Huaxue Xuebao 39 1981 481 483
35. Dahlke, G. D.; Fukushi, T.; Grootaert, W. M. A.; Guerra, M. A.; Qiu, Z. -M. WO2012082551A2, 2012.
36. W.-Y. Huang, B.-N. Huang, and C.-M. Hu J. Fluorine Chem. 23 1983 193 204
37. H.-P. Cao, and Q.-Y. Chen J. Fluorine Chem. 128 2007 1187 1190
38. W.-Y. Huang, B.-N. Huang, and W. Wang Huaxue Xuebao 41 1983 1193 1195
39. W.-Y. Huang, B.-N. Huang, and W. Wang Huaxue Xuebao 44 1986 173 177
40. W.-Y. Huang, F.-H. Wu, and B.-N. Huang Chin. J. Chem. 12 1994 549 551
41. F.-H. Wu, B.-N. Huang, and W.-Y. Huang Chin. J. Chem. 14 1996 373 376
42. B.N. Huang, and J.T. Liu Chin. J. Chem. 1990 358 361
43. B.-N. Huang, and W.-Y. Huang Huaxue Xuebao 42 1984 1106 1108
44. W.-Y. Huang, B.-N. Huang, and C.-M. Hu J. Fluorine Chem. 23 1983 229 240
45. W.-Y. Huang Youji Huaxue 12 1992 12 19
46. F.-H. Wu, B.-N. Huang, and W.-Y. Huang Youji Huaxue 13 1993 449 459
47. W.-Y. Huang Macromol. Symp. 82 1994 67 75
48. W.-Y. Huang J. Fluorine Chem. 58 1992 1 8
49. F.-H. Wu, and W.-Y. Huang Youji Huaxue 17 1997 106 125
50. W.-Y. Huang, and F.-H. Wu Isr. J. Chem. 39 1999 167 170
51. Q.-Y. Chen Isr. J. Chem. 39 1999 179 192
52. G.G. Furin Russ. Chem. Rev. 69 2000 491 522
53. W.-Y. Huang, W. Wang, and B.-N. Huang Huaxue Xuebao 44 1986 488 494
54. W.-Y. Huang, W. Wang, and B.-N. Huang Huaxue Xuebao 43 1985 409 410
55. W.Y. Huang, L. Lu, and Y.-F. Zhang Chin. J. Chem. 1990 68 74
56. W.-Y. Huang, W.-P. Ma, J.-H. Chen, and B. Zhan Youji Huaxue 10 1990 244 247
57. Q. Qi, Q. Shen, and L. Lu J. Fluorine Chem. 133 2012 115 119
58. L.-M. Jin, Z. Zeng, C.-C. Guo, and Q.-Y. Chen J. Org. Chem. 68 2003 3912 3917
59. Z. Zeng, L.-M. Jin, C.-C. Guo, and Q.-Y. Chen Huaxue Xuebao 62 2004 288 294
60. L. Chen, L.-M. Jin, C.-C. Guo, and Q.-Y. Chen Synlett 2005 963 970
61. L.-M. Jin, L. Chen, J.-J. Yin, C.-C. Guo, and Q.-Y. Chen J. Fluorine Chem. 126 2005 1321 1326
62. W.-Y. Huang, and J.-T. Liu Chin. J. Chem. 11 1993 370 375
63. Q.-Y. Chen, and Z.-Y. Yang Huaxue Xuebao 43 1985 1118 1120
64. Q.-Y. Chen, and Z.-Y. Yang Huaxue Xuebao 44 1986 1025 1029
65. Q.-Y. Chen, Y.-B. He, and Z.-Y. Yang J. Fluorine Chem. 34 1986 255 258
66. Q.-Y. Chen, and Z.-Y. Yang Youji Huaxue 6 1986 41 43
67. Q.-Y. Chen, and Z.-Y. Yang J. Chem. Soc., Chem. Commun. 1986 498 499
68. Q.-Y. Chen, and Z.-M. Qiu Youji Huaxue 7 1987 44 46
69. Q.-Y. Chen, and Z.-M. Qiu Huaxue Xuebao 46 1988 38 41
70. Q.-Y. Chen, and Z.-M. Qiu Huaxue Xuebao 46 1988 258 263
71. Q.-Y. Chen, Y.-B. He, and Z.-Y. Yang Huaxue Xuebao 46 1988 779 783
72. K. Von Werner J. Fluorine Chem. 28 1985 229 233
73. Q.-Y. Chen, and Z.-Y. Yang Huaxue Xuebao 44 1986 806 811
74. Q.-Y. Chen, Z.-Y. Yang, and Z.-M. Qiu Chin. Sci. Bull. 33 1988 1866 1868
75. Q.-Y. Chen, and Z.-Y. Yang J. Fluorine Chem. 35 1987 78-78
76. D.Y. Mikhaylov, Y.H. Budnikova, T.V. Gryaznova, D.V. Krivolapov, I.A. Litvinov, D.A. Vicic, and O.G. Sinyashin J. Organomet. Chem. 694 2009 3840 3843
77. T. Takagi, and T. Kanamori J. Fluorine Chem. 132 2011 427 429
78. Q.-Y. Chen, and Z.-Y. Yang J. Fluorine Chem. 39 1988 217 226
79. Q.-Y. Chen, Z.-Y. Yang, and D.-Q. Rong J. Fluorine Chem. 29 1985 147-147
80. Q.-Y. Chen, Z.-Y. Yang, and Y.-B. He J. Fluorine Chem. 37 1987 171 176
81. Z.-Y. Long, and Q.-Y. Chen J. Fluorine Chem. 91 1998 95 98
82. Q.-Y. Chen, and Z.-M. Qiu J. Fluorine Chem. 39 1988 289 292
83. J. Ma, H. Huang, R. Wu, J. Chen, and X. Dai Huaxue Xuebao 47 1989 720 723
84. C.-M. Hu, and X.-Q. Tang J. Fluorine Chem. 61 1993 217 222
85. Q.-Y. Chen, Z.-Y. Yang, C.-X. Zhao, and Z.-M. Qiu J. Chem. Soc., Perkin Trans. 1 1988 563 567
86. Q.-Y. Chen, and Z.-Y. Yang J. Fluorine Chem. 28 1985 399 411
87. Q.-Y. Chen, and Z.-Y. Yang Huaxue Xuebao 44 1986 265 269
88. Q.-Y. Chen, Z.-M. Qiu, and Z.-Y. Yang J. Fluorine Chem. 36 1987 149 161
89. O.R. Pierce, A.E. Meiners, and E.T. McBee J. Am. Chem. Soc. 75 1953 2516-2516
90. O.R. Pierce, and M. Levine J. Am. Chem. Soc. 75 1953 1254-1254
91. A.L. Henne, and W.C. Francis J. Am. Chem. Soc. 73 1951 3518-3518
92. E.T. McBee, C.W. Roberts, and A.F. Meiners J. Am. Chem. Soc. 79 1957 335 337
93. R.N. Haszeldine J. Chem. Soc. 1952 3423 3428
94. R.N. Haszeldine Nature 168 1951 1028 1031
95. C.F. Smith, E.J. Soloski, and C. Tamborski J. Fluorine Chem. 4 1974 35 45
96. Q.-Y. Chen, and J.-G. Chen Youji Huaxue 10 1990 179 183
97. E.T. McBee, C.W. Roberts, and S.G. Curtis J. Am. Chem. Soc. 77 1955 6387 6390
98. R.D. Chambers, and D.J. Spring J. Chem. Soc. 1968 2394 2397
99. H. Gopal, and C. Tamborski J. Fluorine Chem. 13 1979 337 351
100. H. Gopal, E.J. Soloski, and C. Tamborski J. Fluorine Chem. 12 1978 111 121
101. L.S. Chen, G.J. Chen, M.T. Ryan, and C. Tamborski J. Fluorine Chem. 34 1987 299 311
102. B.A. Omotowa, and J.M. Shreeve Organometallics 19 2000 2664 2670
103. B.A. Omotowa, R.L. Kirchmeier, and J.M. Shreeve Inorg. Chem. 38 1999 6055 6059
104. Q.-Y. Chen, Y.-X. Chen, and W.-Y. Huang Huaxue Xuebao 42 1984 906 912
105. Q.-Y. Chen, and Z.-Y. Yang Huaxue Xuebao 43 1985 1073 1078
106. Y.-X. Chen, and Q.-Y. Chen Youji Huaxue 1985 464 470
107. Q.-Y. Chen, and M.-F. Chen J. Fluorine Chem. 49 1990 107 114
108. Q.-Y. Chen, D.-B. Su, Z.-Y. Yang, and R.-X. Zhu J. Fluorine Chem. 36 1987 483 489
109. Y.-X. Chen, S.-R. Ji, C.-Y. Guo, and Q.-Y. Chen Huaxue Xuebao 40 1982 904 912
110. J.D. Park, F.E. Rogers, and J.R. Iacher J. Org. Chem. 26 1961 2089 2095
111. Q.-Y. Chen, and Z.-T. Li J. Chem. Soc., Perkin Trans. 1 1992 1443 1445
112. Q.-Y. Chen, and Z.-T. Li J. Chem. Soc., Perkin Trans. 1 1993 1705 1710
113. Q.-Y. Chen, Z.-T. Li, and C.-M. Zhou J. Chem. Soc., Perkin Trans. 1 1993 2457 2462
114. Z.-M. Qiu, and D.J. Burton J. Org. Chem. 60 1995 3465 3472
115. H.K. Nair, and D.J. Burton J. Am. Chem. Soc. 119 1997 9137 9143
116. M. Kato, and M. Yamabe J. Chem. Soc., Chem. Commun. 1981 1173 1174
117. C.-M. Hu, and Z.-Q. Xu Huaxue Xuebao 48 1990 936 938
118. L.F. Chen, J. Mohtasham, and G.L. Gard J. Fluorine Chem. 43 1989 329 347
119. C.-Y. Guo, and Q.-Y. Chen Huaxue Xuebao 42 1984 592 595
120. Q.-Y. Chen, and J.-G. Chen Huaxue Xuebao 46 1988 301 304
121. X.-C. Guo, and Q.-Y. Chen J. Fluorine Chem. 88 1998 63 70
122. G.-F. Chen, Y.-H. Zhang, and X.-K. Jiang J. Fluorine Chem. 49 1990 263 268
123. X.-K. Jiang Pure Appl. Chem. 62 1990 189 194
124. B.-N. Huang, F.-H. Wu, and C.-M. Zhou J. Fluorine Chem. 75 1995 1 5
125. K.J. Klabunde J. Am. Chem. Soc. 92 1970 2427 2432
126. S. Terabe, and R. Konaka Bull. Chem. Soc. Jpn. 46 1973 825 829
127. Y. Katsumura, K. Ishigure, and Y. Tabata J. Phys. Chem. 82 1979 3152 3161
128. L.H. Sutcliffe, and A. Zilynk J. Chem. Soc., Faraday Trans. 1 81 1985 679 686
129. C.-P. Zhang, H. Wang, A. Klein, C. Biewer, K. Stirnat, Y. Yamaguchi, L. Xu, V. Gomez-Benitez, and D.A. Vicic J. Am. Chem. Soc. 135 2013 8141 8144
130. V.N. Boiko, M.G. Shchupak, and L.M. Yagupolskii Zh. Org. Khim. 13 1977 1057 1061
131. V.I. Popov, V.N. Boik, and L.M. Yagupolskii J. Fluorine Chem. 21 1982 365 369
132. A.E. Feiring J. Fluorine Chem. 24 1984 191 203
133. D. Cantacuzene, C. Wakselman, and R.J. Dorme J. Chem. Soc., Perkin Trans. 1 1977 1365 1371
134. A.E. Feiring J. Org. Chem. 48 1983 347 354
135. D.-Y. Zhou, H.-Y. Dou, C.-X. Zhao, and Q.-Y. Chen J. Fluorine Chem. 127 2006 740 745
136. Q.-Y. Chen, and M.-J. Chen J. Fluorine Chem. 51 1991 21 32
137. Q.-Y. Chen, and Z.-M. Qiu J. Fluorine Chem. 35 1987 343 357
138. Q.-Y. Chen, and Z.-M. Qiu J. Chem. Soc., Chem. Commun. 1987 1240 1241
139. Y. Guo, and Q.-Y. Chen J. Fluorine Chem. 102 2000 105 109
140. N. Kornblum, P. Ackermann, and R.T. Swiger J. Org. Chem. 45 1980 5294 5298
141. G.A. Russell, and F. Ros J. Am. Chem. Soc. 104 1982 7349 7351
142. Q.-Y. Chen, and Z.-M. Qiu J. Fluorine Chem. 31 1986 301 317
143. Q.-Y. Chen, M.-F. Chen, and R.-X. Zhu Huaxue Xuebao 48 1990 162 167
144. R.W. Haszeldine J. Chem. Soc. 1953 2622 2626
145. N.F. Cheetham, and A.D.E. Pullin J. Chem. Soc., Chem. Commun. 1965 418 419
146. O. Hassel Science 170 1970 497 498
147. N.F. Cheetham, and A.D.E. Pullin Aust. J. Chem. 24 1971 479 487
148. A. Mishra, and A.D.E. Pullin Aust. J. Chem. 24 1971 2493 2507
149. N.F. Cheetham, I.J. McNaught, and A.D.E. Pullin Aust. J. Chem. 27 1974 973 985
150. N.F. Cheetham, I.J. McNaught, and A.D.E. Pullin Aust. J. Chem. 27 1974 987 1007
151. I.J. McNaught, and A.D.E. Pullin Aust. J. Chem. 27 1974 1009 1015
152. Q.-Y. Chen, Z.-T. Li, and C.-M. Zhou J. Chem. Soc., Perkin Trans. 1 1993 2457 2462
153. Q.-Y. Chen, and Z.-M. Qiu J. Fluorine Chem. 35 1987 79-79
154. V. Amico, S.V. Meille, E. Corradi, M.T. Messina, and G. Resnati J. Am. Chem. Soc. 120 1998 8261 8262
155. E. Corradi, S.V. Meille, M.T. Messina, P. Metrangolo, and G. Resnati Tetrahedron Lett. 40 1999 7519 7523
156. G. Valerio, G. Raos, S.V. Meille, P. Metrangolo, and G. Resnati J. Phys. Chem. 104 2000 1617 1620
157. P. Cardillo, E. Corradi, A. Lunghi, S.V. Meille, M.T. Messina, P. Metrangolo, and G. Resnati Tetrahedron 56 2000 5535 5550
158. P. Metrangolo, and G. Resnati Chem. - Eur. J. 7 2001 2511 2519
159. D.D. Burton, F. Fontana, P. Metrangolo, T. Pilatid, and G. Resnatic Tetrahedron Lett. 44 2003 645 648
160. K. Raatikainen, J. Huuskonen, M. Lahtinen, P. Metrangolo, and K. Rissanen Chem. Commun. 2009 2160 2162
161. S.-Z. Zhu, C.-H. Xing, W. Xu, and Z.-T. Li Tetrahedron Lett. 45 2004 777 780
162. A.C. Legon Chem. - Eur. J. 4 1998 1890 1897
163. A.C. Legon Angew. Chem., Int. Ed. 38 1999 2686 2714
164. M.T. Messina, P. Metrangolo, W. Panzeri, T. Pilati, and G. Resnati Tetrahedron 57 2001 8543 8550
165. A. Farina, S.V. Meille, M.T. Messina, P. Metrangolo, and G. Resnati Angew. Chem., Int. Ed. 38 1999 2433 2436
166. Y.-Z. Huang, and Q.-L. Zhou J. Org. Chem. 52 1987 3552 3558
167. Y.-Z. Huang, Q.-L. Zhou, and J.-S. Li Youji Huaxue 1985 332 334
168. Y.Z. Huang, and Q.L. Zhou Tetrahedron Lett. 27 1986 2397 2400
169. Q.L. Chu, Z. Wang, Q. Huang, C. Yan, and S.Z. Zhu J. Am. Chem. Soc. 123 2001 11069 11070
170. C.-P. Zhang, Q.-Y. Chen, J.-C. Xiao, and Y.-C. Gu J. Fluorine Chem. 130 2009 671 673
171. W.-Y. Huang, and H.-Z. Zhang J. Fluorine Chem. 50 1990 133 140
172. D.-B. Su, Q.-Y. Chen, and R.-X. Zhu Youji Huaxue 1986 112 120
173. D.-B. Su, Q.-Y. Chen, R.-X. Zhu, and H.-P. Hu Huaxue Xuebao 41 1983 946 959
174. C. Lu, W. Jiang, T. Hickman, and D.D. DesMarteau J. Org. Chem. 76 2011 2896 2898
175. Kaneko, I.; Kanba, M.; Watakabe, A.; Miyake, H. JP 63083138 A, 1988.
176. Tayanagi, J.; Watakabe, A.; Saito, S.; Ueno, K. WO 2004066426A1, 2004.
177. Tayanagi, J.; Watakabe, A.; Saito, M.; Ueno, K. JP 2006032157A, 2006.
178. W.-Y. Huang, B.-N. Huang, and C.-M. Hu Gaofenzi Tongxun 1985 28 34
179. W. Cen, Z.-X. Dong, T.-J. Huang, D.-B. Su, and J.M. Shreeve Inorg. Chem. 27 1988 1376 1377
180. W.-M. Qiu, and D.J. Burton J. Fluorine Chem. 62 1993 273 281
181. L. Zhang, W.R. Dolbier Jr., B. Sheeller, and K.U. Ingold J. Am. Chem. Soc. 124 2002 6362 6366
182. Z. Li, Y.-H. Hou, and Z.-H. Li Xiangsu Ziyuan Liyong 2008 13 17
183. M.A. Harmer, Q. Sun, M.J. Michalczyk, and Z.-Y. Yang Chem. Commun. 1997 1803 1804
184. D. Dube, M. Rat, W. Shen, B. Nohair, F. Beland, and S. Kaliaguine Appl. Catal., A 358 2009 232 239
185. Y. Yin, G. Zhao, and G.-L. Li Tetrahedron 61 2005 12042 12052
186. J.-H. Lin, C.-P. Zhang, Z.-Q. Zhu, Q.-Y. Chen, and J.-C. Xiao J. Fluorine Chem. 130 2009 394 398
187. M. Shirai, and M. Tsunooka Prog. Polym. Sci. 21 1996 1 45
188. J.V. Crivello J. Polym. Sci., Part A: Polym. Chem. 37 1999 4241 4254
189. H. Ito J. Polym. Sci., Part A: Polym. Chem. 41 2003 3863 3870
190. H. Ito Adv. Polym. Sci. 172 2005 37 245
191. P.J. Serafinowski, and P.B. Garland J. Am. Chem. Soc. 125 2003 962 965
192. W. Zhou, S.M. Kuebler, K.L. Braun, T. Yu, J.K. Cammack, C.K. Ober, J.W. Perry, and S.R. Marder Science 296 2002 1106 1109
193. E. Menard, M.A. Meitl, Y. Sun, J.-U. Park, D.J.-L. Shir, Y.-S. Nam, S. Jeon, and J.A. Rogers Chem. Rev. 107 2007 1117 1160
194. D.A. Doshi, I.K. Huesing, M. Lu, H. Fan, Y. Lu, K. Simmons-Potter, B.G. Potter, A.J. Hurd, and J. Brinker Science 290 2000 107 111
195. Y. Yi, R. Ayothi, Y. Wang, M. Li, G. Barclay, R. Sierra-Alvarez, and C.K. Ober Chem. Mater. 21 2009 4037 4046
196. Y. Cho, C.Y. Ouyang, M. Krysak, W. Sun, V. Gamez, R. Sierra-Alvarez, and C.K. Ober Proc. SPIE 7972 2011 79722A1-79722A11
197. L.-F. Chen, J.-H. Wang, and C.-M. Hu Huaxue Xuebao 40 1982 964 968
198. J.-S. Wang, H.-Z. Zhang, W.-Y. Huang, and X.-K. Jiang Tetrahedron 50 1994 10459 10466
199. Z.-Y. Yang, and R.G. Rajendran Angew. Chem., Int. Ed. 44 2005 564 567
200. K. Yoshimura, and K. Iwasaki Macromolecules 42 2009 9302 9306
201. T. Shimura, K. Miyatake, and M. Watanabe Bull. Chem. Soc. Jpn. 83 2010 960 968
202. Q.-Y. Chen, R.-X. Zhu, Z.-Z. Li, S.-D. Wang, and W.-Y. Huang Huaxue Xuebao 40 1982 337 352
203. W.-Y. Huang, X.-M. Du, Y.-Q. He, H.-S. Huang, W.-J. Cao, and C.-P. Luo Huaxue Xuebao 40 1982 821 827
204. Q.-Y. Chen, and S.-Z. Zhu Huaxue Xuebao 41 1983 1153 1163
205. Q.-Y. Chen, and Z.-Y. Yang Youji Huaxue 1987 143 145
206. Q.-Y. Chen, and S.-Z. Zhu Huaxue Xuebao 41 1983 1044 1057
207. Q.-Y. Chen, and S.-Z. Zhu Huaxue Xuebao 40 1982 670 673
208. J.F. Snyder, J.C. Hutchison, M.A. Ratner, and D.F. Shriver Chem. Mater. 15 2003 4223 4230
209. L.J. Brown, D.R. Bouvet, S. Champion, A.M. Gibson, Y. Hu, A. Jackson, I. Khan, N. Ma, N. Millot, H. Wadsworth, and R.C.D. Brown Angew. Chem., Int. Ed. 46 2007 941 944
210. L.J. Brown, N. Ma, D.R. Bouvet, S. Champion, A.M. Gibson, Y. Hu, A. Jackson, I. Khan, N. Millot, A.C. Topley, H. Wadsworth, D. Wynn, and R.C.D. Brown Org. Biomol. Chem. 7 2009 564 575
211. Brown, L. J.; Brown, R. C. D.; Wadsworth, H. J.; Jackson, A. WO2005012319A1, 2005.
212. B. Beuthien- Baumann, K. Hamacher, F. Oberdorfer, and J. Steinbach Carbohydr. Res. 327 2000 107 118
213. T. Ido, C. Wan, V. Casella, J.S. Fowler, A.P. Wolf, M. Reivich, and D.E. Kuhl J. Labelled Compd. Radiopharm. 14 1978 175 183
214. Y. Kuge, K. Nishijima, K. Nagatsu, K. Seki, K. Ohkura, A. Tanaka, M. Sasaki, E. Tsukamoto, and N. Tamaki Nucl. Med. Biol. 29 2002 275 279
215. Z. Zhu, W.-S. Tian, and Q. Liao Tetrahedron Lett. 37 1996 8553 8556
216. W.-S. Tian, Z. Lei, L. Chen, and Y. Huang J. Fluorine Chem. 101 2000 305 308
217. Y. Pan, and C.P. Holmes Org. Lett. 3 2001 2769 2771
218. Q.-Y. Chen, Y.-B. He, and Z.-Y. Yang J. Chem. Soc., Chem. Commun. 1986 1452 1453
219. Y. Pan, B. Ruhland, and C.P. Holmes Angew. Chem., Int. Ed. 40 2001 4488 4491
220. W.-Y. Huang, C.-M. Hu, and H.-Y. Lu Huaxue Xuebao 41 1983 448 456
221. W.-M. Qiu, and D.J. Burton J. Fluorine Chem. 60 1993 93 100
222. L.-F. Chen, J.-H. Wang, and W.-Y. Huang Huaxue Xuebao 41 1983 860 864
223. Y. Lan, Y. Xu, X. Xu, and W. Ge Pige Keji 1988 20 22
224. Y. Xu, Y. Lan, X. Xu, and W. Ge Xibei Qinggongye Xueyuan Xuebao 1988 10 15
225. S.-Z. Zhu, J. Zhang, B. Xu, and A.-W. Li Phosphorus, Sulfur Silicon Relat. Elem. 89 1994 77 82
226. C.-Y. Guo, R.L. Kirchmeier, and J.M. Shreeve J. Am. Chem. Soc. 113 1991 9000 9001
227. C.-P. Zhang, Z.-L. Wang, Q.-Y. Chen, C.-T. Zhang, Y.-C. Gu, and J.-C. Xiao J. Fluorine Chem. 131 2010 761 766
228. W. Lwowski, and T.W. Mattingly Tetrahedron Lett. 1962 277 280
229. M.F. Slon, T.J. Prosser, N.R. Newburg, and D.S. Breglow Tetrahedron Lett. 1964 2945 2959
230. W. Lwowski, and T.J. Maricich J. Am. Chem. Soc. 87 1965 3630 3637
231. R.A. Abramovitch, G.N. Knaus, and V. Uma J. Am. Chem. Soc. 91 1969 7532 7533
232. R. Poe, J. Grayzar, M.J.T. Young, E. Leyva, K.A. Schnapp, and M.S. Platz J. Am. Chem. Soc. 113 1991 3209 3211
233. J.K. Ruff Inorg. Chem. 4 1965 567 570
234. N. Kamigata, K. Yamamoto, O. Kawakita, K. Hiktta, H. Matsuyama, M. Yoshida, and M. Kobayash Bull. Chem. Soc. Jpn. 57 1984 3601 3602
235. S.-Z. Zhu Tetrahedron Lett. 33 1992 6503 6504
236. S.-Z. Zhu J. Chem. Soc., Perkin Trans. 1 1994 2077 2081
237. C.-M. Zhou, S.-Z. Zhu, Y.-H. Zhang, B. Xu, J. Zhang, and X.-K. Jiang J. Fluorine Chem. 73 1995 175 178
238. J. Foropoulos Jr., and D.D. DesMarteau Inorg. Chem. 23 1984 3720 3723
239. S. Singh, and D.D. DesMarteau Inorg. Chem. 29 1990 2982 2985
240. L.-Q. Hu, and D.D. DesMarteau Inorg. Chem. 32 1993 5007 5010
241. X. Hao, A. Yoshida, and J. Nishikido J. Fluorine Chem. 127 2006 193 199
242. B.H. Thomas, G. Shafer, J.-J. Ma, M.-H. Tu, and D.D. DesMarteau J. Fluorine Chem. 125 2004 1231 1240
243. L. Conte, G. Gambaretto, G. Caporiccio, F. Alessandrinic, and S. Passerinic J. Fluorine Chem. 125 2004 243 252
244. J. Zhang, D.D. DesMarteau, S. Zuberi, J.-J. Ma, L. Xue, S.M. Gillette, H. Blau, and R. Gerhardt J. Fluorine Chem. 116 2002 45 48
245. S.-Z. Zhu, G.-F. Jin, and D.D. DesMarteau Chin. J. Chem. 20 2002 1268 1273
246. W.B. Cen, and Y.C. Shen J. Fluorine Chem. 52 1991 369 375
247. D.-B. Su, W. Cen, R.L. Kirchmeier, and J.M. Shreeve Can. J. Chem. 67 1989 1795 1799
248. R. Arvai, F. Toulgoat, B.R. Langlois, J.-Y. Sanchez, and M. Médebielle Tetrahedron 65 2009 5361 5368
249. C.-P. Zhang, Z.-L. Wang, Q.-Y. Chen, C.-T. Zhang, Y.-C. Gu, and J.-C. Xiao Eur. J. Inorg. Chem. 2010 3419 3422
250. T. Welton Chem. Rev. 99 1999 2071 2083
251. J. Dupont, R.F. Souza, and P.A.Z. Suarez Chem. Rev. 102 2002 3667 3692
252. P. Wasserscheid, and W. Keim Angew. Chem., Int. Ed. 39 2000 3772 3789
253. R. Sheldon Chem. Commun. 2001 2399 2407
254. P. Wasserscheid, and T. Welton Ionic Liquids in Synthesis 2003 Wiley-VCH Weinheim, Germany
255. A. Corma, and H. Garcia Chem. Rev. 103 2003 4307 4366
256. W.S. Miao, and T.H. Chan Acc. Chem. Res. 39 2006 897 908
257. M. Smiglak, A. Metlen, and R. Rogers Acc. Chem. Res. 40 2007 1182 1192
258. R. Sheldon Chem. Commun. 2001 2399 2407
259. M. Yoshizawa, A. Narita, and H. Ohno Aust. J. Chem. 57 2004 139 144
260. C.M. Gorden Appl. Catal., A 222 2001 101 117
261. H. Zhao, S.Q. Xia, and P.S. Ma J. Chem. Technol. Biotechnol. 80 2005 1089 1096
262. C.-P. Zhang, Z.-L. Wang, Q.-Y. Chen, C.-T. Zhang, Y.-C. Gu, and J.-C. Xiao Glob. J. Inorg. Chem. 1 2010 115 118