How to lose a bond in two ways - The diradical/zwitterion dichotomy in cycloaromatization reactions

European Journal of Organic Chemistry

Volumn , Issue 13, 2013, Pages 2505-2527

  Peterson, Paul W ^a   Mohamed, Rana K ^a   Alabugin, Igor V ^a  

^a FLORIDA STATE UNIVERSITY   (United States)

Author keywords

Cycloaromatization; Radicals; Reaction mechanisms; Zwitterions

Indexed keywords

EID: 84876517807     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201201656     Document Type: Article

References (212)

1. R. R. Jones, R. G. Bergman, J. Am. Chem. Soc. 1972, 94, 660.
2. R. G. Bergman, Acc. Chem. Res. 1973, 6, 25.
3. A. G. Myers, E. Y. Kuo, N. S. Finney, J. Am. Chem. Soc. 1989, 111, 8057.
4. A. G. Myers, P. S. Dragovich, E. Y. Kuo, J. Am. Chem. Soc. 1992, 114, 9369.
5. R. Nagata, H. Yamanaka, E. Okazaki, I. Saito, Tetrahedron Lett. 1989, 30, 4995.
6. R. Nagata, H. Yamanaka, E. Murahashi, I. Saito, Tetrahedron Lett. 1990, 31, 2907.
7. A. G. Myers, P. S. Dragovich, J. Am. Chem. Soc. 1989, 111, 9130.
8. K. C. Nicolaou, A. L. Smith, E. W. Yue, Proc. Natl. Acad. Sci. USA 1993, 90, 5881.
9. I. A. Maretina, B. A. Trofimov, Russ. Chem. Rev. 2006, 75, 825.
10. A. Polukhtine, G. Karpov, D. R. Pandithavidana, A. Kuzmin, V. V. Popik, Aust. J. Chem. 2010, 63, 1099.
11. M. Jean, S. Tomasi, P. van de Weghe, Org. Biomol. Chem. 2012, 10, 7453.
12. M. C. Joshi, D. S. Rawat, Chem. Biodiversity 2012, 9, 459.
13. U. Galm, M. H. Hager, S. G. V. Lanen, J. Ju, J. S. Thorson, B. Shen, Chem. Rev. 2005, 105, 739.
14. R. Nagata, H. Yamanaka, E. Okazaki, I. Saito, Tetrahedron Lett. 1989, 30, 4995.
15. I. Suzuki, A. Shigenaga, A. Manabe, H. Nemoto, M. Shibuya, Tetrahedron 2003, 59, 5691.
16. J. W. Grissom, G. U. Gunawardena, D. Klingberg, D. Huang, Tetrahedron 1996, 52, 6453.
17. R. Gleiter, D. Kratz, Angew. Chem. 1993, 105, 884;
18. Angew. Chem. Int. Ed. Engl. 1993, 32, 842.
19. J. A. John, J. M. Tour, J. Am. Chem. Soc. 1994, 116, 5011.
20. J. A. John, J. M. Tour, Tetrahedron 1997, 53, 15515.
21. H. V. Shah, D. A. Babb, D. W. Smith Jr., Polymer 2000, 41, 4415.
22. X. Chen, L. M. Tolbert, D. W. Hess, C. Henderson, Macromolecules 2001, 34, 4104.
23. J. P. Johnson, D. A. Bringley, E. E. Wilson, K. D. Lewis, L. W. Beck, A. J. Matzger, J. Am. Chem. Soc. 2003, 125, 14708.
24. D. Smith Jr, H. V. Shah, K. P. Perera, U. M. W. Perpall, D. A. Babb, S. J. Martin, Adv. Funct. Mater. 2007, 17, 1237.
25. J. D. Rule, J. S. Moore, Macromolecules 2005, 38, 7266.
26. K. K. Wang, Chem. Rev. 1996, 96, 207.
27. X. Yang, Z. Li, J. Zhi, J. Ma, A. Hu, Langmuir 2010, 26, 11244.
28. B. Zhu, J. Ma, Z. Li, J. Hou, X. Cheng, G. Qian, P. Liu, A. Hu, J. Mater. Chem. 2011, 21.
29. Z. Li, D. Song, J. Zhi, A. J. Hu, Phys. Chem. C 2011, 115, 15829.
30. M. Prall, A. Wittkopp, P. A. Schreiner, J. Phys. Chem. A 2001, 105, 9265.
31. C. Vavilala, N. Byrne, C. M. Kraml, D. M. Ho, R. A. Pascal, J. Am. Chem. Soc. 2008, 130, 13549.
32. B. Engels, C. Lennartz, M. Hanrath, M. Schmittel, M. Strittmatter, Angew. Chem. 1998, 110, 2067;
33. Angew. Chem. Int. Ed. 1998, 37, 1960.
34. M. Schmittel, S. Kiau, T. Siebert, M. Strittmatter, Tetrahedron Lett. 1996, 37, 7691.
35. M. Schmittel, M. Keller, S. Kiau, M. Strittmatter, Chem. Eur. J. 1997, 3, 807.
36. M. Schmittel, M. Strittmer, S. Kiau, Tetrahedron Lett. 1995, 36, 4975.
37. M. Kar, A. Basak, Chem. Rev. 2007, 107, 2861.
38. I. V. Alabugin, S. V. Kovalenko, J. Am. Chem. Soc. 2002, 124, 9052.
39. I. V. Alabugin, M. Manoharan, J. Am. Chem. Soc. 2003, 125, 4495.
40. H. Hopf, H. Musso, Angew. Chem. 1969, 81, 704;
41. Angew. Chem. Int. Ed. Engl. 1969, 8, 680.
42. H. Hopf, A. Kruger, P. R. Schreiner, Chem. Eur. J. 2001, 7, 4386.
43. S. Braverman, D. Segev, J. Am. Chem. Soc. 1974, 96, 1245.
44. P. J. Garratt, S. B. Neoh, J. Am. Chem. Soc. 1975, 97, 3255.
45. Y. Zafrani, H. E. Gottlieb, M. Sprecher, S. Braverman, J. Org. Chem. 2005, 70, 10166.
46. R. W. Sullivan, V. M. Coghlan, S. A. Munk, M. W. Reed, H. W. Moore, J. Org. Chem. 1994, 59, 2276.
47. H. Li, H. Yang, J. L. Petersen, K. K. Wang, J. Org. Chem. 2004, 69, 4500.
48. M. Schmittel, J.-P. Steffen, B. Engels, C. Lennartz, M. Hanrath, Angew. Chem. 1998, 110, 2531;
49. Angew. Chem. Int. Ed. 1998, 37, 2371.
50. M. Schmittel, J. P. Steffen, M. A. Wencesla Ángel, B. Engels, C. Lennartz, M. Hanrath, Angew. Chem. 1998, 110, 1633;
51. Angew. Chem. Int. Ed. 1998, 37, 1562.
52. B. Engels, M. Hanrath, J. Am. Chem. Soc. 1998, 120, 6356.
53. A. Navarro-Vazquez, M. Prall, P. R. Schreiner, Org. Lett. 2004, 6, 2981.
54. J. M. Galbraith, P. R. Schreiner, N. R. Harris, W. Wei, A. Wittkopp, S. Shaik, Chem. Eur. J. 2000, 6, 1446, other cycloaromatization reactions can be considered interrupted [2+2] cycloadditions; for an extended MO analysis of Bergman cyclization reactions, see
55. I. V. Alabugin, M. Manoharan, J. Phys. Chem. A 2003, 107, 3363.
56. A. Basak, S. Mandal, S. S. Bag, Chem. Rev. 2003, 103, 4077.
57. M. Klein, T. Walenzyk, B. König, Collect. Czech. Chem. Commun. 2004, 69, 945.
58. D. S. Rawat, J. M. Zaleski, Synlett 2004, 393.
59. P. R. Schreiner, A. Navarro-Vazquez, M. Prall, Acc. Chem. Res. 2005, 38, 29.
60. I. V. Alabugin, B. Breiner, M. Manoharan, Adv. Phys. Org. Chem. 2007, 42, 1.
61. G. B. Jones, K. C. Russell, CRC Handbook of Organic Photochemistry and Photobiology, 2nd ed., CRC Press, Boca Raton, FL, 2004, pp. 29/1-29/21.
62. I. V. Alabugin, W.-Y. Yang, R. Pal, CRC Handbook of Organic Photochemistry and Photobiology (Eds:, A. Griesbeck, M. Oelgemöller, F. E Ghetti), Taylor & Francis, Boca Raton, FL, 2012.
63. B. Breiner, K. Kaya, S. Roy, W.-Y. Yang, I. V. Alabugin, Org. Biomol. Chem. 2012, 10, 3974.
64. M. Schmittel, C. Vavilala, M. E. Cinara, J. Phys. Org. Chem. 2012, 25, 182.
65. H. Sugiyama, K. Yamashita, M. Nishi, I. Saito, Tetrahedron Lett. 1992, 33, 515.
66. H. Sugiyama, K. Yamashita, T. Fujiwara, I. Saito, Tetrahedron 1994, 50, 1311.
67. M. Shibuya, M. Wakayama, Y. Naoe, T. Kawakami, K. Ishigaki, H. Nemoto, H. Shimizu, Y. Nagao, Tetrahedron Lett. 1996, 37, 865.
68. W. T. Borden, Encyclopedia of Computational Chemistry (Ed.:, P. von R. Schleyer,), Wiley-Interscience, New York, 1998, pp. 708-722.
69. W. T. Borden, H. Iwamura, J. A. Berson, Acc. Chem. Res. 1994, 27, 109.
70. C. R. Flynn, J. Michl, J. Am. Chem. Soc. 1974, 96, 3280.
71. J. Michl, V. Bonačic̈-Koutecký, Tetrahedron 1988, 44, 7559.
72. V. Bonačicc̈-Koutecký, V. Koutecký, J. J. Michl, Angew. Chem. 1987, 99, 216;
73. Angew. Chem. Int. Ed. Engl. 1987, 26, 170.
74. L. Salem, C. Rowland, Angew. Chem. 1972, 84, 86;
75. Angew. Chem. Int. Ed. Engl. 1972, 11, 92.
76. R. A. Moss, Acc. Chem. Res. 1989, 22, 15.
77. A. J. Arduengo III, Acc. Chem. Res. 1999, 32, 913.
78. T. Tezuka, O. Kikuchi, K. N. Houk, M.-N. Paddon-Row, C. M. Santiago, N. G. Rondan, J. C. Williams Jr, G. W. Gandour, J. Am. Chem. Soc. 1981, 103, 1367.
79. V. Bonacic-Koutecky, P. Bruckmann, P. Hiberty, J. Koutecky, C. Leforestier, L. Salem, Angew. Chem. 1975, 87, 599;
80. Angew. Chem. Int. Ed. Engl. 1975, 14, 575.
81. W. Domcke, A. Viel, R. P. Krawczyk, U. Manthe, Angew. Chem. 2003, 115, 3556;
82. Angew. Chem. Int. Ed. 2003, 42, 3434.
83. L. Salem, Science 1976, 191, 822 also see work on twisted intramolecular charge-transfer (TICT) excited states
84. Z. R. Grabowski, K. Rotkiewicz, W. Rettig, Chem. Rev. 2003, 103, 3899.
85. J. Dobkowski, J. Wojcik, W. Kozminski, R. Kolos, J. Waluk, J. Michl, J. Am. Chem. Soc. 2002, 124, 2406.
86. K. A. Zachariasse, S. I. Druzhinin, W. Bosch, R. Machinek, J. Am. Chem. Soc. 2004, 126, 1705.
87. R. Hoffmann, A. Imamura, W. J. Hehre, J. Am. Chem. Soc. 1968, 90, 1499.
88. R. Hoffmann, Acc. Chem. Res. 1971, 4, 1.
89. R. Gleiter, W. Schafer, Acc. Chem. Res. 1990, 23, 369.
90. F. C. Pickard IV, R. L. Shepherd, A. E. Gillis, M. E. Dunn, S. Feldgus, K. N. Kirschner, G. C. Shields, M. Manoharan, I. V. Alabugin, J. Phys. Chem. A 2006, 110, 2517.
91. Squires and co-workers proposed a spin-polarization mechanism for such coupling, see:, P. G. Wenthold, S. G. Wierschke, J. J. Nash, R. R. Squires, J. Am. Chem. Soc. 1994, 116, 7378.
92. V. Richter, Ber. Dtsch. Chem. Ges. 1883, 16, 677.
93. S. F. Vasilevsky, E. V. Tretyakov, H. D. Verkruijsse, Synth. Commun. 1994, 24, 1733.
94. S. F. Vasilevsky, E. V. Tretyakov, Liebigs Ann. 1995, 775.
95. E. V. Tretyakov, S. F. Vasilevsky, Mend. Commun. 1996, 190.
96. E. V. Tretyakov, D. W. Knight, S. F. Vasilevsky, J. Chem. Soc. Perkin Trans. 1 1999, 3721.
97. O. N. Vinogradova, V. N. Sorokoumov, S. F. Vasilevsky, I. A. Balova, Tetrahedron Lett. 2007, 48, 4907.
98. C. Vavilala, N. Byrne, C. M. Krami, D. M. Ho, R. A. Pascal Jr., J. Am. Chem. Soc. 2008, 130, 13549.
99. A. A. Stepanov, L. M. Gornostaev, S. F. Vasilevsky, E. V. Arnold, V. I. Mamatyuk, D. S. Fadeev, B. Gold, I. V. Alabugin, J. Org. Chem. 2011, 76, 8737.
100. B. Godoi, R. F. Schumacher, G. Zeni, Chem. Rev. 2011, 111, 2937 for a general discussion of electronic effects in alkyne cyclization reactions, see
101. K. Gilmore, I. V. Alabugin, Chem. Rev. 2011, 111, 6513.
102. I. Alabugin, K. Gilmore, M. Manoharan, J. Am. Chem. Soc. 2011, 133, 12608.
103. P. E. Peterson, R. J. Kamat, J. Am. Chem. Soc. 1969, 91, 4521.
104. M. Hanack, Acc. Chem. Res. 1976, 9, 364.
105. M. Hanack, Angew. Chem. 1978, 90, 346;
106. Angew. Chem. Int. Ed. Engl. 1978, 17, 333.
107. W. S. Johnson, L. R. Hughes, J. L. Carlson, J. Am. Chem. Soc. 1979, 101, 1281.
108. M. Hanack, C. J. Collins, H. Stutz, B. M. Benjamin, J. Am. Chem. Soc. 1981, 103, 2356.
109. C. J. Collins, M. Hanack, H. Stutz, G. Auchter, W. Schoberth, J. Org. Chem. 1983, 48, 5260.
110. Y. Apeloig, J. B. Collins, D. Cremer, T. Bally, E. Haselbach, J. A. Pople, J. Chandrasekhar, P. v. R. Schleyer, J. Org. Chem. 1980, 45, 3496.
111. W. Franke, H. Schwarz, J. Org. Chem. 1981, 46, 2806.
112. A. Cunje, C. F. Rodriquez, M. H. Lien, A. C. Hopkinson, J. Org. Chem. 1996, 61, 5212.
113. T. Jin, M. Himuro, Y. Yamamoto, Angew. Chem. 2009, 121, 6007;
114. Angew. Chem. Int. Ed. 2009, 48, 5893.
115. J. J. Jaber, K. Mitsui, S. D. Rychnovsky, J. Org. Chem. 2001, 66, 4679.
116. A. Balog, D. P. Curran, J. Org. Chem. 1995, 60, 337;
117. for a recent review on Prins-type cyclization reactions, see:, C. Olier, M. Kaafarani, S. Gastaldi, M. P. Bertrand, Tetrahedron 2010, 66, 413, and references cited therein.
118. L. E. Overman, M. J. Sharp, J. Am. Chem. Soc. 1988, 110, 612.
119. For an overview of hydrogen shifts accompanied by aromatization, see:, I. V. Alabugin, M. Manoharan, B. Breiner, F. Lewis, J. Am. Chem. Soc. 2003, 125, 9329.
120. A. Poloukhtine, V. Rassadin, A. Kuzmin, V. V. Popik, J. Org. Chem. 2010, 75, 5953.
121. S. R. Brunette, M. A. Lipton, J. Org. Chem. 2000, 65, 5114.
122. M. K. Waddell, T. Bekele, M. Lipton, J. Org. Chem. 2006, 71, 8372.
123. A. Arcadi, O. A. Attanasi, B. Guidi, E. Rossi, S. Santeusanio, Eur. J. Org. Chem. 1999, 11, 3117.
124. M.-J. Wu, L.-J. Chang, L.-M. Wei, C.-F. Lin, Tetrahedron 1999, 55, 13193.
125. L. Liu, Y. Wang, C. Peng, J. Zhao, Q. Zhu, Tetrahedron Lett. 2009, 50, 6715.
126. J.-M. Tang, T.-A. Liu, R.-S. Liu, J. Org. Chem. 2008, 73, 8479.
127. S. F. Vasilevsky, T. F. Mikhailovskaya, V. I. Mamatyuk, G. E. Salnikov, G. A. Bogdanchikov, M. Manoharan, I. V. Alabugin, J. Org. Chem. 2009, 74, 8106.
128. H. W. Whitlock Jr, P. E. Sandvick, L. E. Overman, P. B. Reichardt, J. Org. Chem. 1969, 34, 879.
129. C. L. Perrin, B. L. Rodgers, J. M. O'Connor, J. Am. Chem. Soc. 2007, 129, 4795.
130. A. G. Myers, E. Y. Kuo, N. S. Finney, J. Am. Chem. Soc. 1989, 111, 8057.
131. A. G. Myers, P. S. Dragovich, E. Y. Kuo, J. Am. Chem. Soc. 1992, 114, 9369.
132. A. V. Kuzman, V. V. Popik, Chem. Commun. 2009, 38, 5707.
133. T. S. Hughes, B. K. Carpenter, J. Chem. Soc. Perkin Trans. 2 1999, 11, 2291.
134. Configuration interaction (CI) calculations with localized molecular orbitals (LMOs) by Sakai and Nishitani suggested that the population of the two frontier natural orbitals in the product are 1.0 and 1.0e, which indicates a perfect diradical:, S. Sakai, M. Nishitani, J. Phys. Chem. A 2010, 114, 11807.
135. B. K. Carpenter, Chem. Soc. Rev. 2006, 35, 736.
136. P. Lechtken, R. Breslow, A. H. Schmidt, N. J. Turro, J. Am. Chem. Soc. 1973, 95, 3025.
137. N. J. Turro, G. Schuster, J. Poulique, R. Pettit, C. Mauldin, J. Am. Chem. Soc. 1974, 96, 6797.
138. S. Miki, H. Kagawa, Z. Yoshida, J. Phys. Org. Chem. 1992, 5, 101.
139. W. M. David, S. M. Kerwin, J. Am. Chem. Soc. 1997, 119, 1464.
140. J. Hoffner, M. J. Schottelius, D. Feichtinger, P. Chen, J. Am. Chem. Soc. 1998, 120, 376.
141. C. J. Cramer, J. Am. Chem. Soc. 1998, 120, 6261 see also
142. E. Kraka, D. Cremer, J. Am. Chem. Soc. 2000, 122, 8245.
143. C. Laroche, J. Li, C. Gonzales, W. M. David, S. M. Kerwin, Org. Biomol. Chem. 2010, 8, 1535 for earlier work, see
144. A. K. Nadipuram, S. M. Kerwin, Org. Lett. 2002, 4, 4543.
145. A. K. Nadipuram, S. M. Kerwin, Synlett 2004, 8, 1404.
146. A. K. Nadipuram, S. M. Kerwin, Tetrahedron Lett. 2006, 47, 353.
147. A. K. Nadipuram, S. M. Kerwin, Tetrahedron 2006, 62, 3798.
148. I. Suzuki, M. Wakayama, A. Shigenaga, H. Nemoto, M. Shibuya, Tetrahedron Lett. 2000, 41, 10019.
149. L. Feng, D. Kumar, D. M. Bimey, S. M. Kerwin, Org. Lett. 2004, 6, 2059.
150. P. R. Schreiner, B. Bui, Org. Lett. 2003, 5, 4871.
151. M. J. Wu, C. F. Lin, S. H. Chen, F. C. Lee, J. Chem. Soc. 1999, 20, 2875.
152. 6 in the presence of excess 1,4-cyclohexadiene at 200 °C for 30 min, see:, K. K. Wang, Z. Wang, P. D. Sattsangi, J. Org. Chem. 1996, 61, 1516.
153. O. H. W. Decker, H. W. Moore, Chem. Rev. 1986, 86, 821.
154. H. Li, J. L. Petersen, K. K. Wang, J. Org. Chem. 2003, 68, 5512.
155. M. Schmittel, J. Steffen, D. Rodrbox drawings light down and leftguez, B. Engelen, E. Neumann, M. E. Cinar, J. Org. Chem. 2008, 73, 3005.
156. This discussion will not include the large body of elegant work based on metal complexation with other functional groups of substituted enediynes. For selected examples, see:, P. J. Benites, R. C. Holmberg, D. S. Rawat, B. J. Kraft, L. J. Klein, D. G. Peters, H. H. Thorp, J. M. Zaleski, J. Am. Chem. Soc. 2003, 125, 6434.
157. P. J. Benites, R. C. Holmberg, D. S. Rawat, B. J. Kraft, L. J. Klein, D. G. Peters, H. H. Thorp, J. M. Zaleski, J. Am. Chem. Soc. 2003, 125, 6434.
158. P. J. Benites, R. C. Holmberg, D. S. Rawat, B. J. Kraft, L. J. Klein, D. G. Peters, H. H. Thorp, J. M. Zaleski, J. Am. Chem. Soc. 2003, 125, 6434
159. for reviews, see:, P. J. Benites, R. C. Holmberg, D. S. Rawat, B. J. Kraft, L. J. Klein, D. G. Peters, H. H. Thorp, J. M. Zaleski, J. Am. Chem. Soc. 2003, 125, 6434.
160. S. S. Bhattacharyya, J. M. Zaleski, Prog. Inorg. Chem. 2007, 55, 355.
161. I. V. Alabugin, K. Gilmore, P. W. Peterson, WIREs Comput. Mol. Sci. 2011, 1, 109.
162. I. V. Alabugin, M. Manoharan, T. A. Zeidan, J. Am. Chem. Soc. 2003, 125, 14014.
163. I. V. Alabugin, M. Manoharan, J. Org. Chem. 2004, 69, 9011.
164. P. H. Cheong, P. Morganelli, M. R. Luzung, K. N. Houk, F. D. Toste, J. Am. Chem. Soc. 2008, 130, 4517.
165. A. S. K. Hashmi, I. Braun, M. Rudolph, F. Rominger, Organometallics 2012, 31, 644.
166. L. Ye, Y. Wang, D. H. Aue, L. Zhang, J. Am. Chem. Soc. 2012, 134, 31.
167. A. S. K. Hashmi, I. Braun, P. Nösel, J. Schädlich, M. Wieteck, M. Rudolph, F. Rominger, Angew. Chem. 2012, 124, 4532;
168. Angew. Chem. Int. Ed. 2012, 51, 4456.
169. W. Hou, Z. Zhang, F. Kong, S. Wang, H. Wang, Z.-J. Yao, Chem. Commun. 2013, 49, 695.
170. S. Naoe, Y. Suzuki, K. Hirano, Y. Inaba, S. Oishi, N. Fujii, H. Ohno, J. Org. Chem. 2012, 77, 4907.
171. S. F. Vasilevsky, D. S. Baranov, V. I. Mamatyuk, Y. V. Gatilov, I. V. Alabugin, J. Org. Chem. 2009, 74, 6143.
172. D. S. Baranov, S. F. Vasilevsky, B. Gold, I. V. Alabugin, RSC Adv. 2011, 1, 1745.
173. K. Gilmore, M. Manoharan, J. Wu, P. v. R. Schleyer, I. V. Alabugin, J. Am. Chem. Soc. 2012, 134, 10584.
174. P. M. Byers, J. I. Rashid, R. K. Mohamed, I. V. Alabugin, Org. Lett. 2012, 14, 6032.
175. for intramolecular initiation by the "weak link" design, see:, P. M. Byers, I. V. Alabugin, J. Am. Chem. Soc. 2012, 134, 9609.
176. I. V. Alabugin, K. Gilmore, S. Patil, M. Manoharan, S. V. Kovalenko, R. J. Clark, I. Ghiviriga, J. Am. Chem. Soc. 2008, 130, 11535;
177. J. Zhao, C. O. Hughes, F. D. Toste, J. Am. Chem. Soc. 2006, 128, 7436.
178. Y. Chen, M. Chen, Y. Liu, Angew. Chem. 2012, 124, 6599;
179. Angew. Chem. Int. Ed. 2012, 51, 6493.
180. D. V. Vidhani, J. W. Cran, M. E. Krafft, M. Manoharan, I. V. Alabugin, J. Org. Chem. 2012,.
181. D. V. Vidhani, J. W. Cran, M. E. Krafft, I. V. Alabugin, Org. Biomol. Chem.
182. Q. Wang, S. Aparaj, N. G. Akhmedov, J. L. Petersen, X. Shi, Org. Lett. 2012, 14, 1334.
183. A. Odedra, C.-J. Wu, T. P. Pratap, C.-W. Huang, Y.-F. Ran, R.-S. Liu, J. Am. Chem. Soc. 2005, 127, 3406.
184. Y. Wang, M. G. Finn, J. Am. Chem. Soc. 1995, 117, 8045.
185. K. Ohe, M.-A. Kojima, K. Yohehara, S. Uemura, Angew. Chem. 1996, 108, 1959;
186. Angew. Chem. Int. Ed. Engl. 1996, 35, 1823.
187. T. Manabe, S.-I. Yanagi, K. Ohe, S. Uemura, Organometallics 1998, 17, 2942.
188. K. Ohe, Bull. Korean Chem. Soc. 2007, 28, 2153.
189. B. P. Taduri, Y. F. Ran, C. Huang, R. S. Liu, Org. Lett. 2006, 8, 883.
190. L. J. K. Boerner, M. Nath, M. Pink, J. M. Zaleski, Chem. Eur. J. 2011, 17, 9311.
191. Q. Huang, J. A. Hunter, R. C. Larock, J. Org. Chem. 2002, 67, 3437.
192. G. Dai, R. C. Larock, Org. Lett. 2001, 3, 4035.
193. K. R. Roesch, R. C. Larock, J. Org. Chem. 1998, 63, 5306.
194. Q. Ding, Z. Chen, X. Yu, Y. Peng, J. Wu, Tetrahedron Lett. 2009, 50, 340.
195. Z. Chen, X. Yang, J. Wu, Chem. Commun. 2009, 23, 3469.
196. N. Ghavtadze, R. Fröhlich, E.-U. Würthwein, Eur. J. Org. Chem. 2010, 9, 1787.
197. Z. Huo, H. Tomeba, Y. Yamamoto, Tetrahedron Lett. 2008, 49, 5531.
198. D. Fischer, H. Tomeba, N. K. Pahadi, N. T. Patil, Y. Yamamoto, Angew. Chem. 2007, 119, 4848;
199. Angew. Chem. Int. Ed. 2007, 46, 4764.
200. D. Fischer, H. Tomeba, N. K. Pahadi, N. T. Patil, Z. Huo, Y. Yamamoto, J. Am. Chem. Soc. 2008, 130, 15720.
201. Y.-N. Niu, Z.-Y. Yan, G.-L. Gau, H.-L. Wang, X.-Z. Shu, K.-G. Ji, Y.-M. Liang, J. Org. Chem. 2009, 74, 2893.
202. Z. Chen, L. Gao, S. Ye, Q. Ding, J. Wu, Chem. Commun. 2012, 48, 3975.
203. L. Gao, S. Ye, Q. Ding, Z. Chen, J. Wu, Tetrahedron 2012, 68, 2765.
204. S. Li, J. Wu, Org. Lett. 2011, 13, 712.
205. S. Li, Y. Luo, J. Wu, Org. Lett. 2011, 13, 4312.
206. Z. Chen, X. Pan, J. Wu, Synlett 2011, 964.
207. Z. Chen, J. Wu, Org. Lett. 2010, 12, 4856.
208. S. Ye, X. Yang, J. Wu, Chem. Commun. 2010, 46, 5238.
209. X. Yu, S. Ye, J. Wu, Adv. Synth. Catal. 2010, 352, 2050.
210. Z. Chen, Q. Ding, X. Yu, J. Wu, Adv. Synth. Catal. 2009, 351, 1692.
211. Z. Chen, M. Su, X. Yu, J. Wu, J. Org. Biomol. Chem. 2009, 7, 4641.
212. P. Huang, Q. Yang, Z. Chen, Q. Ding, J. Xu, Y. Peng, J. Org. Chem. 2012, 77, 8092.