Mechanism of trifluoromethylation of aryl halides with CuCF3and the ortho effect

Journal of the American Chemical Society

Volumn 136, Issue 38, 2014, Pages 13410-13425

  Konovalov, Andrey I ^a   Lishchynskyi, Anton ^a   Grushin, Vladimir V ^a  

^a INSTITUTE OF CHEMICAL RESEARCH OF CATALONIA ICIQ   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

FREE ENERGY; GROUND STATE; METAL HALIDES;

ELECTRONIC FACTORS; LINEAR CORRELATION; MOLECULAR STRAIN; OXIDATIVE ADDITIONS; RATE DETERMINING STEP; REACTION PATHWAYS; TRANSITION STATE; TRIFLUOROMETHYLATION;

CARBON DIOXIDE;

BENZENE DERIVATIVE; COPPER COMPLEX; CUPRIC ION; CUPROUS ION; HALIDE; REAGENT;

ADDITION REACTION; ARTICLE; CHEMICAL BOND; CHEMICAL INTERACTION; DISSOCIATION; ELECTRON TRANSPORT; METHYLATION; OXIDATION; REACTION ANALYSIS; SUBSTITUTION REACTION; TRIFLUOROMETHYLATION;

EID: 84912554206     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja507564p     Document Type: Article

References (197)

1. (a) McLoughlin, V. C. R.; Thrower, J. U.S. Patent 3408411, 1968.
2. (b) McLoughlin, V. C. R.; Thrower, J. Tetrahedron 1969, 25, 5921.
3. For selected monographs, see: (a) Hudlicky, M. Chemistry of Organic Fluorine Compounds; Ellis Horwood: New York, 1976.
4. (b) Banks, R. E. Organofluorine Chemicals and Their Industrial Applications; Ellis Horwood: West Sussex, U.K., 1979.
5. (c) Filler, R.; Kobayashi, Y. Biomedicinal Aspects of Fluorine Chemistry; Kodansha- Elsevier: New York, 1982.
6. (d) Clark, J. H.; Wails, D.; Bastock, T. W. Aromatic Fluorination; CRC Press: Boca Raton, FL, 1996.
7. (e) Kirsch, P. Modern Fluoroorganic Chemistry; Wiley-VCH: Weinheim, 2004.
8. (f) Uneyama, K. Organofluorine Chemistry; Blackwell: Oxford, U.K., 2006.
9. (g) Ojima, I. Fluorine in Medicinal Chemistry and Chemical Biology; Wiley-Blackwell: Chichester, U.K., 2009.
10. (h) Petrov, V. A. Fluorinated Heterocyclic Compounds. Synthesis, Chemistry and Applications; Wiley: Hoboken, NJ, 2009.
11. For selected reviews, see: (a) Burton, D. J.; Yang, Z. Y. Tetrahedron 1992, 48, 189.
12. (b) McClinton, M. A.; McClinton, D. A. Tetrahedron 1992, 48, 6555.
13. (c) Burton, D. J.; Lu, L. Top. Curr. Chem. 1997, 193, 45.
14. (d) Schlosser, M. Angew. Chem., Int. Ed. 2006, 45, 5432.
15. (e) Roy, S.; Gregg, B. T.; Gribble, G. W.; Le, V.-D.; Roy, S. Tetrahedron 2011, 67, 2161.
16. (f) Qing, F.-L.; Zheng, F. Synlett 2011, 1052.
17. (g) Liu, T.; Shen, Q. Eur. J. Org. Chem. 2012, 6679.
18. (h) Lishchynskyi, A.; Novák, P.; Grushin, V. V. In Science of Synthesis: C-1 Building Blocks in Organic Synthesis 2; van Leeuwen, P. W. N. M., Ed.; Thieme: Stuttgart, 2013; p 367.
19. For a recent comprehensive review of aromatic trifluoromethylation and perfluoroalkylation, see: Tomashenko, O. A.; Grushin, V. V. Chem. Rev. 2011, 111, 4475.
20. For most recent reports not covered in the review article cited in ref 4, see: (a) Zhang, C. P.; Wang, Z. L.; Chen, Q. Y.; Zhang, C. T.; Gu, Y. C.; Xiao, J. C. Angew. Chem., Int. Ed. 2011, 50, 1896.
21. (b) Popov, I.; Lindeman, S.; Daugulis, O. J. Am. Chem. Soc. 2011, 133, 9286.
22. (c) Morimoto, H.; Tsubogo, T.; Litvinas, N. D.; Hartwig, J. F. Angew. Chem., Int. Ed. 2011, 50, 3793.
23. (d) Tomashenko, O. A.; Escudero-Ada'n, E. C.; Martínez Belmonte, M.; Grushin, V. V. Angew. Chem., Int. Ed. 2011, 50, 7655.
24. (e) Weng, Z.; Lee, R.; Jia, W.; Yuan, Y.; Wang, W.; Feng, X.; Huang, K.-W. Organometallics 2011, 30, 3229.
25. (f) Li, Y.; Chen, T.; Wang, H.; Zhang, R.; Jin, K.; Wang, X.; Duan, C. Synlett 2011, 1713.
26. (g) Kondo, H.; Oishi, M.; Fujikawa, K.; Amii, H. Adv. Synth. Catal. 2011, 353, 1247.
27. (h) Kremlev, M. M.; Mushta, A. I.; Tyrra, W.; Yagupolskii, Y. L.; Naumann, D.; Mö ller, A. J. Fluorine Chem. 2012, 133, 67.
28. (i) Sanhueza, I. A.; Nielsen, M. C.; Ottiger, M.; Schoenebeck, F. Helv. Chim. Acta 2012, 95, 2231.
29. (j) Chen, M.; Buchwald, S. L. Angew. Chem., Int. Ed. 2013, 52, 11628.
30. (k) Serizawa, H.; Aikawa, K.; Mikami, K. Chem. - Eur. J. 2013, 19, 17692.
31. (l) Mulder, J. A.; Frutos, R. P.; Patel, N. D.; Qu, B.; Sun, X.; Tampone, T. G.; Gao, J.; Sarvestani, M.; Eriksson, M. C.; Haddad, N.; Shen, S.; Song, J. J.; Senanayake, C. H. Org. Process Res. Dev. 2013, 17, 940.
32. (m) Nakamura, Y.; Fujiu, M.; Murase, T.; Itoh, Y.; Serizawa, H.; Aikawa, K.; Mikami, K. Beilstein J. Org. Chem. 2013, 9, 2404.
33. Mormino, M. G. Fier, P. S. Hartwig, J. F.Org. Lett.2014161744
34. (o) Serizawa, H.; Aikawa, K.; Mikami, K. Org. Lett. 2014, 16, 3456.
35. (p) Gonda, Z.; Kovács, S.; Wéber, C.; Gáti, T.; Mészáros, A.; Kotschy, A.; Novák, Z. Org. Lett. 2014, 16, 4268.
36. For the original reports on Cu-catalyzed trifluoromethylation of aryl halides (iodides), see: (a) Oishi, M.; Kondo, H.; Amii, H. Chem. Commun. 2009, 1909.
37. (b) Inoue, M.; Araki, K. Japan Patent JP 2009- 234921, 2009.
38. (a) Kobayashi, Y.; Kumadaki, I. Tetrahedron Lett. 1969, 4095.
39. For a recent account of Kumadaki's work, see: Sato, K.; Tarui, A.; Omote, M.; Ando, A.; Kumadaki, I. Synthesis 2010, 1865.
40. Kondratenko, N. V.; Vechirko, E. P.; Yagupolskii, L. M. Synthesis 1980, 932.
41. Matsui, K.; Tobita, E.; Ando, M.; Kondo, K. Chem. Lett. 1981, 1719.
42. (a) Wiemers, D. M.; Burton, D. J. J. Am. Chem. Soc. 1986, 108, 832.
43. (b) MacNeil, J. G.; Burton, D. J. J. Fluorine Chem. 1991, 55, 225.
44. (a) Chen, Q.-Y.; Wu, S.-W. J. Chem. Soc., Chem. Commun. 1989, 705.
45. (b) Chen, Q.-Y.; Wu, S.-W. J. Chem. Soc., Perkin Trans. 1 1989, 2385.
46. (c) Chen, Q.-Y.; Duan, J.-X. J. Chem. Soc., Chem. Commun. 1993, 1389.
47. (d) Long, Z.-Y.; Duan, J.-X.; Lin, Y.-B.; Guo, C.-Y.; Chen, Q.-Y. J. Fluorine Chem. 1996, 78, 177.
48. Chen, G. J.; Tamborski, C. J. Fluorine Chem. 1989, 43, 207.
49. Urata, H.; Fuchikami, T. Tetrahedron Lett. 1991, 32, 91.
50. (a) Kuett, A.; Movchun, V.; Rodima, T.; Dansauer, T.; Rusanov, E. B.; Leito, I.; Kaljurand, I.; Koppel, J.; Pihl, V.; Koppel, I.; Ovsjannikov, G.; Toom, L.; Mishima, M.; Medebielle, M.; Lork, E.; Rö schenthaler, G.- V.; Koppel, I. A.; Kolomeitsev, A. A. J. Org. Chem. 2008, 73, 2607.
51. (b) Kremlev, M. M.; Tyrra, W.; Mushta, A. I.; Naumann, D.; Yagupolskii, Y. L. J. Fluorine Chem. 2010, 131, 212.
52. (a) Dubinina, G. G.; Furutachi, H.; Vicic, D. A. J. Am. Chem. Soc. 2008, 130, 8600.
53. (b) Dubinina, G. G.; Ogikubo, J.; Vicic, D. A. Organometallics 2008, 27, 6233.
54. Carr, G. E.; Chambers, R. D.; Holmes, T. F. J. Chem. Soc., Perkin Trans. 1 1988, 921.
55. For selected reviews, see: (a) Hassan, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359.
56. (b) Ley, S.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400.
57. (c) Beletskaya, I. P.; Cheprakov, A. V. Coord. Chem. Rev. 2004, 248, 2337.
58. (d) Evano, G.; Blanchard, N.; Toumi, M. Chem. Rev. 2008, 108, 3054.
59. (d) Monnier, F.; Taillefer, M. Angew. Chem., Int. Ed. 2009, 48, 6954.
60. (e) Rao, H.; Fu, H. Synlett 2011, 745.
61. Copper-Mediated Cross-Coupling Reactions; Evano, G., Blanchard, N., Eds.; John Wiley & Sons: Hoboken, NJ, 2014.
62. For most recent critical reviews of mechanisms of Cu-mediated/ catalyzed coupling reactions of aryl halides, see: (a) Beletskaya, I. P.; Cheprakov, A. V. Organometallics 2012, 31, 7753.
63. Lefèvre, G.; Franc, G.; Tlili, A.; Adamo, C.; Taillefer, M.; Ciofini, I.; Jutand, A. Organometallics 2012, 31, 7694.
64. (c) Sperotto, E.; van Klink, G. P. M.; van Koten, G.; de Vries, J. G. Dalton Trans. 2010, 39, 10338.
65. (a) Jones, G. O.; Liu, P.; Houk, K. N.; Buchwald, S. L. J. Am. Chem. Soc. 210, 132, 6205.
66. (b) Yu, H.-Z.; Jiang, Y.-Y.; Fu, Y.; Liu, L. J. Am. Chem. Soc. 2010, 132, 18078.
67. (a) Zanardi, A.; Novikov, M. A.; Martin, E.; Benet-Buchholz, J.; Grushin, V. V. J. Am. Chem. Soc. 2011, 133, 20901.
68. (b) Mazloomi, Z.; Bansode, A.; Benavente, P.; Lishchynskyi, A.; Urakawa, A.; Grushin, V. V. Org. Process Res. Dev. 2014, 18, 1020.
69. Grushin, V. V. Chim. Oggi 2014, 32, 81.
70. Konovalov, A. I.; Benet-Buchholz, J.; Martin, E.; Grushin, V. V. Angew. Chem., Int. Ed. 2013, 52, 11637.
71. Novák, P.; Lishchynskyi, A.; Grushin, V. V. Angew. Chem., Int. Ed. 2012, 51, 7767.
72. Novák, P.; Lishchynskyi, A.; Grushin, V. V. J. Am. Chem. Soc. 2012, 134, 16167.
73. Lishchynskyi, A.; Novikov, M. A.; Martin, E.; Escudero-Adán, E. C.; Novák, P.; Grushin, V. V. J. Org. Chem. 2013, 78, 11126.
74. Lishchynskyi, A.; Berthon, G.; Grushin, V. V. Chem. Commun. 2014, 50, 10237.
75. For related transformations involving C2F5H-derived CuC2F5, see: Lishchynskyi, A.; Grushin, V. V. J. Am. Chem. Soc. 2013, 135, 12584.
76. (a) Bunnett, J. F. Acc. Chem. Res. 1978, 11, 413.
77. RN1 Mechanism; American Chemical Society: Washington, DC, 1983.
78. (c) Bowman, W. R.; Heaney, H.; Smith, P. H. G. Tetrahedron Lett. 1984, 25, 5821.
79. (d) van Leeuwen, M.; McKillop, A. J. Chem. Soc., Perkin Trans. 1 1993, 2433.
80. Giese, B.; Kopping, B.; Göbel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. 1996, 48, 301.
81. (a) Johnston, L. J.; Lusztyk, J.; Wayner, D. D. M.; Abeywickreyma, A. N.; Beckwith, A. L. J.; Scaiano, J. C.; Ingold, K. U. J. Am. Chem. Soc. 1985, 107, 4594.
82. (b) Abeywickrema, A. N.; Beckwith, A. L. J. Chem. Commun. 1986, 464.
83. (c) Abeywickrema, A. N.; Beckwith, A. L. J.; Gerba, S. J. Org. Chem. 1987, 52, 4072.
84. (d) Annunziata, A.; Galli, C.; Marinelli, M.; Pau, T. Eur. J. Org. Chem. 2001, 1323.
85. (a) Creutz, S. E.; Lotito, K. J.; Fu, G. C.; Peters, J. C. Science 2012, 338, 647.
86. (b) Uyeda, C.; Tan, Y.; Fu, G. C.; Peters, J. C. J. Am. Chem. Soc. 2013, 135, 9548.
87. Fier, P. S.; Hartwig, J. F. J. Am. Chem. Soc. 2012, 134, 10795.
88. (a) Combes, S.; Finet, J.-P. Tetrahedron 1999, 55, 3377.
89. (b) Tye, J. W.; Weng, Z.; Johns, A. M.; Incarvito, C. D.; Hartwig, J. F. J. Am. Chem. Soc. 2008, 130, 9971.
90. (c) Tye, J. W.; Weng, Z.; Giri, R.; Hartwig, J. F. Angew. Chem., Int. Ed. 2010, 49, 2185.
91. (d) Giri, R.; Hartwig, J. F. J. Am. Chem. Soc. 2010, 132, 15860.
92. (e) Chen, C.; Weng, Z.; Hartwig, J. F. Organometallics 2012, 31, 8031.
93. (f) Huang, Z.; Hartwig, J. F. Angew. Chem., Int. Ed. 2012, 51, 1028.
94. (g) Chatterjee, T.; Ranu, B. C. J. Org. Chem. 2013, 78, 7145.
95. (h) Gurung, S. K.; Thapa, S.; Vangala, A. S.; Giri, R. Org. Lett. 2013, 15, 5378.
96. (i) Chen, C.; Ouyang, L.; Lin, Q.; Liu, Y.; Hou, C.; Yuan, Y.; Weng, Z. Chem. - Eur. J. 2014, 20, 657.
97. (j) Chen, C.; Hou, C.; Wang, Y.; Hor, T. S. A.; Weng, Z. Org. Lett. 2014, 16, 524.
98. (a) Exner, O.; Böhm, S. Curr. Org. Chem. 2006, 10, 763.
99. (b) Exner, O.; Böhm, S. Phys. Chem. Chem. Phys. 2004, 6, 3864.
100. (c) Exner, O.; Bö hm, S. Org. Biomol. Chem. 2005, 3, 1838.
101. (d) Exner, O.; Böhm, S. Collect. Czech. Chem. Commun. 2006, 71, 1239.
102. Žáček, P.; Dransfeld, A.; Exner, O.; Schraml, J. Magn. Reson. Chem. 2006, 44, 1073.
103. Hansch, H.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165.
104. Williams, A. L.; Kinney, R. E.; Bridger, R. F. J. Org. Chem. 1967, 32, 2501.
105. Litvak, V. V.; Shein, S. M. Zh. Org. Khim. 1974, 10, 550.
106. Litvak, V. V.; Shein, S. M. Zh. Org. Khim. 1974, 10, 2360.
107. Aronskaya, N. Yu.; Bezuglyi, V. D. Zh. Org. Khim. 1974, 10, 268.
108. Stanko, V. I.; Iroshnikova, N. G. Zh. Obshch. Khim. 1979, 49, 2076.
109. (a) Couture, C.; Paine, A. J. Can. J. Chem. 1985, 63, 111.
110. (b) Paine, A. J. J. Am. Chem. Soc. 1987, 109, 1496.
111. Strieter, E. R.; Bhayana, B.; Buchwald, S. L. J. Am. Chem. Soc. 2009, 131, 78.
112. Ji, P.; Atherton, J. H.; Page, M. I. J. Org. Chem. 2012, 77, 7471.
113. Foà, M.; Cassar, L. J. Chem. Soc., Dalton Trans. 1975, 2572.
114. (a) Ullmann, F. Ber. Dtsch. Chem. Ges. 1903, 36, 2382.
115. (b) Ullmann, F. Ber. Dtsch. Chem. Ges. 1904, 37, 853.
116. (a) Vorozhtsov, N. N., Jr.; Kobelev, V. A. Zh. Obshch. Khim. 1939, 9, 1043.
117. (b) Goldberg, A. A. J. Chem. Soc. 1952, 4368.
118. (c) Mayer, W.; Fikentscher, R. Chem. Ber. 1958, 91, 1536.
119. (c) Vainshtein, F. M.; Tomilenko, E. I.; Shilov, E. A. Doklady Akad. Nauk SSSR 1966, 170, 1077.
120. (d) Vainshtein, F. M.; Tomilenko, E. I.; Shilov, E. A. Kinet. Katal. 1969, 10, 777.
121. (e) Lisitsyn, V. N.; Shestakov, V. A.; Sycheva, E. D. Zh. Vses. Khim. O-va. im. D. I. Mendeleeva 1969, 14, 117.
122. (f) Castro, C. E.; Havlin, R.; Honwad, V. K.; Malte, A.; Moje, S. J. Am. Chem. Soc. 1969, 91, 6464.
123. (g) Drozd, V. N.; Trifonova, O. I. Zh. Org. Khim. 1970, 6, 2493.
124. (h) Bruggink, A.; McKillop, A. Tetrahedron 1975, 31, 2607.
125. For reviews, see: (a) Bunnett, J. F.; Zahler, R. E. Chem. Rev. 1951, 49, 273.
126. (b) Fanta, P. E. Chem. Rev. 1964, 64, 613.
127. (c) Shein, S. M.; Litvak, V. V. Zh. Vses. Khim. O-va. im. D. I. Mendeleeva 1976, 21, 274.
128. (d) Lindley, J. Tetrahedron 1984, 40, 1433.
129. (a) Clark, J. H.; McClinton, M. A.; Blade, R. J. J. Chem. Soc., Chem. Commun. 1988, 638.
130. (b) Clark, J. H.; Denness, J. E.; McClinton, M. A.; Wynd, A. J. J. Fluorine Chem. 1990, 50, 411.
131. See, for example: (a) Strieter, E. R.; Blackmond, D. G.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4120.
132. (b) Zhang, S.-L.; Liu, L.; Fu, Y.; Guo, Q.-X. Organometallics 2007, 26, 4546.
133. (c) Kaddouri, H.; Vicente, V.; Quali, A.; Quazzani, F.; Taillefer, M. Angew. Chem., Int. Ed. 2009, 48, 333.
134. (d) Strieter, E. R.; Bhayana, B.; Buchwald, S. L. J. Am. Chem. Soc. 2009, 131, 78.
135. (e) Zhang, S.-L.; Ding, Y. Organometallics 2011, 30, 633.
136. (f) Liu, X.; Zhang, S.-L.; Ding, Y. Dalton Trans. 2012, 41, 5897.
137. (g) Zhang, S.; Zhu, Z.; Ding, Y. Dalton Trans. 2012, 41, 13832.
138. Yoke, J. T., III; Weiss, J. F.; Tollin, G. Inorg. Chem. 1963, 2, 1210.
139. See, for example: (a) Cioslowski, J.; Liu, G.; Moncrieff, D. J. Phys. Chem. A 1997, 101, 957.
140. (b) Taskinen, E. Struct. Chem. 2000, 11, 293.
141. (c) Al-Muhtaseb, A. H.; Altarawneh, M. Comput. Theor. Chem. 2011, 966, 38.
142. (d) Altarawneh, I.; Altarawneh, M.; Rawadieh, S. Can. J. Chem. 2013, 91, 999.
143. Algarra, A. G.; Grushin, V. V.; Macgregor, S. A. Organometallics 2012, 31, 1467.
144. See also: (a) Goodman, J.; Grushin, V. V.; Larichev, R. B.; Macgregor, S. A.; Marshall, W. J.; Roe, D. C. J. Am. Chem. Soc. 2009, 131, 4236.
145. (b) Goodman, J.; Grushin, V. V.; Larichev, R. B.; Macgregor, S. A.; Marshall, W. J.; Roe, D. C. J. Am. Chem. Soc. 2010, 132, 12013.
146. (a) Miller, J. Aromatic Nucleophilic Substitution; Elsevier: London, 1968.
147. (b) Terrier, F. Nucleophilic Aromatic Displacement: The Influence of the Nitro Group; VCH: New York, 1991.
148. (a) Miller, J. Aust. J. Chem. 1956, 9, 61.
149. (b) Miller, J.; Wan, K.-Y. J. Chem. Soc. 1963, 3492.
150. (a) Ueda, H.; Sakabe, N.; Tanaka, J.; Furusaki, A. Nature 1967, 215, 956.
151. (b) Ueda, H.; Sakabe, N.; Tanaka, J.; Furusaki, A. Bull. Chem. Soc. Jpn. 1968, 41, 2866.
152. (c) Destro, R.; Gramaccioli, C. M.; Simonetta, M. Acta Crystallogr. 1968, B24, 1369.
153. (d) Messmer, G. G.; Palenik, G. J. Acta Crystallogr. 1971, B27, 314.
154. (e) Gitis, S. S.; Kaminskaya, E. G.; Ivanova, A. I.; Grigor'eva, N. V.; Margolis, N. V.; Kaminskii, A. Ya. J. Struct. Chem. 1976, 17, 578.
155. (f) Kaminskaya, E. G.; Gitis, S. S.; Ivanova, A. I.; Margolis, N. V.; Kaminskii, A. Ya.; Grigor 'eva, N. V. J. Struct. Chem. 1977, 18, 309.
156. (g) Destro, R.; Pilati, T.; Simonetta, M. Acta Crystallogr. 1979, B35, 733.
157. (h) Lowe-Ma, C. K. Acta Crystallogr. 1986, C27, 38.
158. (i) Niclas, H. J.; Kind, J.; Ramm, M. J. Prakt. Chem. 1991, 333, 909.
159. (j) Terrier, F.; Lelievre, J.; Chatrousse, A. P.; Boubaker, T.; Bachet, B.; Cousson, A. J. Chem. Soc., Perkin Trans. 2 1992, 361.
160. (k) Borbulevych, O. Y.; Kovalevsky, A. Y.; Shishkin, O. V.; Atroschenko, Y. M.; Alifanova, E. N.; Gitis, S. S.; Kaminsky, A. Y.; Tarasova, E. Y. Monatsh. Chem. 1998, 129, 467.
161. (l) Alifanova, E. N.; Kaminskii, A. Ya.; Bel 'skii, V. K.; Kalnin'sh, K. K.; Tarasova, E. Yu.; Gitis, S. S. Russ. J. Gen. Chem. 1998, 68, 1621.
162. (m) Borbulevych, O. Ya.; Antipin, M. Yu.; Olekhnovich, L. P. Acta Crystallogr. 1999, C55, 2177.
163. (n) Borbulevych, O. Ya.; Shishkin, O. V.; Budarina, Z. N.; Antipin, M. Yu.; Olekhnovich, L. P. Acta Crystallogr. 1999, C55, 1915.
164. (o) Borbulevych, O. Ya.; Shishkin, O. V.; Knyazev, V. N. Acta Crystallogr. 1999, C55, 1704.
165. (p) Borbulevych, O. Ya.; Shishkin, O. V.; Knyazev, V. N. Acta Crystallogr. 1999, C55, 1918.
166. (q) Borbulevych, O. Y.; Antipin, M. Y.; Shishkin, O. V.; Knyazev, V. N. J. Mol. Struct. 2000, 520, 141.
167. (r) Borbulevych, O. Ya.; Antipin, M. Yu.; Shishkin, O. V.; Knyazev, V. N. Russ. Chem. Bull. 2000, 49, 452.
168. (s) Borbulevych, O. Ya.; Shishkin, O. V.; Antipin, M. Yu. J. Phys. Chem. A 2002, 106, 8109.
169. (t) Borbulevych, O. Ya. J. Chem. Cryst. 2005, 35, 777.
170. (u) Galkina, I. V.; Takhautdinova, G. L.; Tudrii, E. V.; Yusupova, L. M.; Krivolapov, D. B.; Litvinov, I. A.; Cherkasov, R. A.; Galkin, V. I. Russ. J. Org. Chem. 2013, 49, 598.
171. Thalladi, V. R.; Goud, B. S.; Hoy, V. J.; Allen, F. H.; Howard, J. A. K.; Desiraju, G. R. Chem. Commun. 1996, 401.
172. Colapietro, M.; Domenicano, A.; Marciante, C.; Portalone, G. Z. Naturforsch., B 1982, 37, 1309;
173. Acta Crystallogr., Sect. A 1981, 37, C199.
174. Maurin, J.; Krygowski, T. M. J. Mol. Struct. 1988, 172, 413.
175. Talberg, H. J. Acta Chem. Scand., Ser. A 1978, 32, 373.
176. (a) Cohen, T.; Wood, J.; Dietz, A. G., Jr. Tetrahedron Lett. 1974, 3555.
177. (b) Cohen, T.; Cristea, I. J. Org. Chem. 1975, 40, 3649.
178. (c) Cohen, T.; Cristea, I. J. Am. Chem. Soc. 1976, 98, 748.
179. Ouali, A.; Spindler, J.-F.; Jutand, A.; Taillefer, M. Adv. Synth. Catal. 2007, 349, 1906.
180. Zhang, Y.; Ding, Y. Organometallics 2011, 30, 633.
181. (a) Casitas, A.; King, A. E.; Parella, T.; Costas, M.; Stahl, S. S.; Ribas, X. Chem. Sci. 2010, 1, 326.
182. (b) Casitas, A.; Canta, M.; Costas, M.; Solà, M.; Ribas, X. J. Am. Chem. Soc. 2011, 133, 19386.
183. (c) Font, M.; Parella, T.; Costas, M.; Ribas, X. Organometallics 2012, 31, 7976.
184. see: Casitas, A.; Ribas, X. Chem. Sci. 2013, 4, 2301.
185. Dahlén, A.; Petersson, A.; Hilmersson, G. Org. Biomol. Chem. 2003, 1, 2423.
186. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, N. J.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö .; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision D.01; Gaussian, Inc., Wallingford CT, 2009.
187. (a) Grimme, S. J. Comput. Chem. 2004, 25, 1463.
188. (b) Grimme, S. J. Comput. Chem. 2006, 27, 1787.
189. Cancès, M. T.; Mennucci, B. B.; Tomasi, J. J. Chem. Phys. 1997, 107, 3032.
190. Andrae, D.; Haussermann, U.; Dolg, M.; Stoll, H.; Preuss, H. Theor. Chim. Acta 1990, 77, 123.
191. Höllwarth, A.; Böhme, M.; Dapprich, S.; Ehlers, A. W.; Gobbi, A.; Jonas, V.; Köhler, K. F.; Stegmann, R.; Veldkamp, A.; Frenking, G. Chem. Phys. Lett. 1993, 208, 237.
192. Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213.
193. Fukui, K. Acc. Chem. Res. 1981, 14, 363.
194. Schwabe, T.; Grimme, S. Phys. Chem. Chem. Phys. 2006, 8, 4398.
195. Ehlers, A. W.; Böhme, M.; Dapprich, S.; Gobbi, A.; Hö llwarth, A.; Jonas, V.; Köhler, K. F.; Stegmann, R.; Veldkamp, A.; Frenking, G. Chem. Phys. Lett. 1993, 208, 111.
196. Frisch, M. J.; Pople, J. A.; Binkley, J. S. J. Chem. Phys. 1984, 80, 3265.
197. Rappé, A. K.; Casewit, C. J.; Colwell, K. S.; Goddard, W. A.; Skiff, W. M. J. Am. Chem. Soc. 1992, 114, 10024.