Recent advances in the C-H-functionalization of the distal positions in pyridines and quinolines

Tetrahedron

Volumn 71, Issue 46, 2015, Pages 8683-8716

  Stephens, David E ^a   Larionov, Oleg V ^a  

^a UNIVERSITY OF TEXAS AT SAN ANTONIO   (United States)

Author keywords

Borylation; C C bond formation; C H functionalization; N Heterocycles; Pyridines; Quinolines; Site selectivity; Transition metal catalysis

Indexed keywords

CARBON; FUNCTIONAL GROUP; HETEROCYCLIC COMPOUND; HYDROGEN; PYRIDINE DERIVATIVE; QUINOLINE DERIVATIVE; TRANSITION ELEMENT;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDROGEN BOND; PRIORITY JOURNAL;

EID: 84943820529     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2015.08.034     Document Type: Review

References (248)

1. L. Ackermann, R. Vicente, and A.R. Kapdi Angew. Chem. 121 2009 9976 10011
2. Angew. Chem., Int. Ed. 2009, 48, 9792-9826
3. O. Daugulis, H.-Q. Do, and D. Shabashov Acc. Chem. Res. 42 2009 1074 1086
4. I.A.I. Mkhalid, J.H. Barnard, T.B. Marder, J.M. Murphy, and J.F. Hartwig Chem. Rev. 110 2010 890 931
5. K.M. Engle, T.-S. Mei, M. Wasa, and J.-Q. Yu Acc. Chem. Res. 45 2011 788 802
6. Y. Nakao Synthesis 20 2011 3209 3219
7. J. Yamaguchi, A.D. Yamaguchi, and K. Itami Angew. Chem., Int. Ed. 51 2012 8960 9009
8. Y.-J. Liu, H. Xu, W.-J. Kong, M. Shang, H.-X. Dai, and J.-Q. Yu Nature 515 2014 389 393
9. G. Yan, A.J. Borah, and M. Yang Adv. Synth. Catal. 356 2014 2375 2394
10. H. Bonin, M. Sauthier, and F.-X. Felpin Adv. Synth. Catal. 356 2014 645 671
11. R. Rossi, F. Bellina, M. Lessi, and C. Manzini Adv. Synth. Catal. 356 2014 17 117
12. T. Iwai, and M. Sawamura ACS Catal. 5 2015 5031 5040
13. A.J. Vetter, C. Flaschenriem, and W.D. Jones J. Am. Chem. Soc. 127 2005 12315 12322
14. E.M. Beck, N.P. Grimster, R. Hatley, and M.J. Gaunt J. Am. Chem. Soc. 128 2006 2528 2529
15. S.R. Neufeldt, and M.S. Sanford Acc. Chem. Res. 45 2012 936 946
16. A.M. Wagner, A.J. Hickman, and M.S. Sanford J. Am. Chem. Soc. 135 2013 15710 15713
17. A.G. Green, P. Liu, C.A. Merlic, and K.N. Houk J. Am. Chem. Soc. 136 2014 4575 4583
18. P. Wen, Y. Li, K. Zhou, C. Ma, X. Lan, C. Ma, and G. Huang Adv. Synth. Catal. 354 2012 2135 2140
19. B. Liu, Y. Huang, J. Lan, F. Songa, and J. You Chem. Sci. 4 2013 2163 2167
20. L.C. Campeau, S. Rousseaux, and K. Fagnou J. Am. Chem. Soc. 127 2005 18020 18021
21. J.-P. Leclerc, and K. Fagnou Angew. Chem. 118 2006 7945 7950
22. Angew. Chem., Int. Ed. 2006, 45, 7781-7786
23. S.H. Cho, S. Hwang, and S. Chang J. Am. Chem. Soc. 130 2008 9254 9256
24. A. Larivee, J.J. Mousseau, and A.B. Charette J. Am. Chem. Soc. 130 2008 52 54
25. L.C. Campeau, D.R. Stuart, J.-P. Leclerc, M. Bertrand-Laperle, E. Villemure, H.Y. Sun, S. Lasserre, N. Guimond, M. Lecavallier, and K. Fagnou J. Am. Chem. Soc. 131 2009 3291 3306
26. J. Wu, X. Cui, L. Chen, G. Jiang, and Y. Wu J. Am. Chem. Soc. 131 2009 13888 13889
27. H.-Y. Sun, S.I. Gorelsky, D.R. Stuart, L.-C. Campeau, and K. Fagnou J. Org. Chem. 75 2010 8180 8189
28. L. Ackermann, and S. Fenner Chem. Commun. 2011 430 432
29. B. Xiao, Z.-J. Liu, L. Liu, and Y. Fu J. Am. Chem. Soc. 135 2013 616 619
30. W. Liu, Y. Li, Y. Wang, and C. Kuang Org. Lett. 15 2013 4682 4685
31. E. Kaneko, Y. Matsumoto, and K. Kamikawa Chem. - Eur. J. 19 2013 11837 11841
32. N.J. Willis, and J.M. Smith RSC Adv. 4 2014 11059 11063
33. W. Liu, X. Yu, Y. Liab, and C. Kuang Chem. Commun. 2014 9291 9294
34. Q. Gao, D.-W. Gu, and S.-L. You ACS Catal. 4 2014 2741 2745
35. R. Suresh, S. Muthusubramanian, R.S. Kumaran, and G. Manickam Asian J. Org. Chem. 3 2014 604 611
36. E. Kianmehr, M. Rezaeefard, M. Rezazadeh Khalkhali, and K.M. Khan RSC Adv. 4 2014 13764 13767
37. H.-Q. Do, R.M. Kashif Khan, and O. Daugulis J. Am. Chem. Soc. 130 2008 15185 15192
38. Q. Xiao, L. Ling, F. Ye, R. Tan, L. Tian, Y. Zhang, Y. Li, and J. Wang J. Org. Chem. 78 2013 3879 3885
39. Z.Y. Wu, H.Y. Song, X.L. Cui, C. Pi, W.W. Du, and Y.J. Wu Org. Lett. 15 2013 1270 1273
40. Y. Shen, J. Chen, M. Liu, J.-C. Ding, W. Gao, X. Huang, and H. Wu Chem. Commun. 2014 4292 4295
41. O.V. Larionov, D. Stephens, A. Mfuh, and G. Chavez Org. Lett. 16 2014 864 867
42. Y. Nakao, K.S. Kanyiva, and T. Hiyama J. Am. Chem. Soc. 130 2008 2448 2449
43. K.S. Kanyiva, Y. Nakao, and T. Hiyama Agnew. Chem., Int. Ed. 46 2007 8872 8874
44. J.C. Lewis, R.G. Bergman, and J.A. Ellman J. Am. Chem. Soc. 129 2007 5332 5333
45. D. Xue, Z.-H. Jia, C.-J. Zhao, Y.-Y. Zhang, C. Wang, and J. Xiao Chem. - Eur. J. 20 2014 2960 2965
46. A. Sugimori, and T. Yamada Bull. Chem. Soc. Jpn. 59 1986 3911 3915
47. L.P. Ivanova, Yu B. Zelechonov, V.V. Zorin, D.L. Rakhmanyulov, and A.A. Kasatkina Zh. Obshch. Khim. 64 1994 333 335
48. F. Minisci, E. Vismara, and F. Fontana J. Org. Chem. 54 1989 5224 5227
49. I.B. Seiple, S. Su, R.A. Rodriguez, R. Gianatassio, Y. Fujiwara, A.L. Sobel, and P.S. Baran J. Am. Chem. Soc. 132 2010 13194 13196
50. Y. Fujiwara, J.A. Dixon, R.A. Rodriguez, R.D. Baxter, D.D. Dixon, M.R. Collins, D.G. Blackmond, and P.S. Baran J. Am. Chem. Soc. 134 2012 1494 1497
51. B.S. Shaibu, R.K. Kawade, and R.-S. Liu Org. Biomol. Chem. 10 2012 6834 6839
52. K. Matcha, and A.P. Antonchick Angew. Chem. 125 2013 8143 8147
53. Angew. Chem., Int. Ed. 2013, 52, 2082-2086
54. P.S. Fier, and J.F. Hartwig Science 342 2013 956 960
55. D.E. Stephens, G. Chavez, M. Valdes, M. Dovalina, H.D. Arman, and O.V. Larionov Org. Biomol. Chem. 12 2014 6190 6199
56. G. Mingat, P. MacLellan, M. Laars, and J. Clayden Org. Lett. 16 2014 1252 1255
57. S.I. Gorelsky, D. Laponite, and K. Fagnou J. Am. Chem. Soc. 130 2008 10848 10849
58. S. Potavathri, K.C. Pereira, S.I. Gorelsky, A. Pike, A.P. LeBris, and B. DeBoef J. Am. Chem. Soc. 132 2010 14676 14681
59. S.I. Gorelsky, D. Laponite, and K. Fagnou J. Org. Chem. 77 2012 658 668
60. S.I. Gorelsky Organometallics 31 2012 794 797
61. A. Petit, J. Flygare, A.T. Miller, G. Winkel, and D.H. Ess Org. Lett. 14 2012 3680 3683
62. S.I. Gorelsky Coord. Chem. Rev. 257 2013 153 164
63. J.P. Michael Nat. Prod. Rep. 24 2007 223 246
64. J. Polanski, A. Kurczyk, A. Bak, and R. Musiol Curr. Med. Chem. 19 2012 1921 1945
65. Y.Y. Zhang, T. Han, Q.L. Ming, L.S. Wu, K. Rahman, and L.P. Qin Nat. Prod. Commun. 7 2012 963 968
66. W.A. Denny, B.F. Cain, G.J. Atwell, C. Hansch, A. Panthananickal, and A. Leo J. Med. Chem. 25 1982 276 315
67. A.B. Burgin, O.T. Magnusson, J. Singh, P. Witte, B.L. Staker, J.M. Bjornsson, M. Thorsteinsdottir, S. Hrafnsdottir, T. Hagen, A.S. Kiselyov, L.J. Stewart, and M.E. Gurney Nat. Biotechnol. 28 2010 63 70
68. P. Ashok, S. Ganguly, and S. Murugesan Drug Discov. Today 19 2014 1781 1791
69. A.M. Mfuh, and O.V. Larionov Curr. Med. Chem. 2015 10.2174/0929867322666150619104007
70. G. Yang, Y. Si, and Z. Su Org. Biomol. Chem. 10 2012 8418 8425
71. G. Hughes, and M.R. Bryce J. Mater. Chem. 15 2005 94 107
72. M. Nakajima, M. Saito, M. Shiro, and S.-I. Hashimoto J. Am. Chem. Soc. 120 1998 6419 6420
73. M. Saito, M. Nakajima, and S.-I. Hashimoto Chem. Commun. 2000 1851 1852
74. S.E. Denmark, and Y. Fan J. Am. Chem. Soc. 124 2002 4233 4235
75. X.H. Bei, D.C. Swenson, and R.F. Jordan Organometallics 16 1997 3282 3302
76. R. Fu, M.E. O'Reilly, R.J. Nielsen, W.A. Goddard, and T.B. Gunnoe Chem. - Eur. J. 21 2015 1286 1293
77. J. Takagi, K. Sato, J.F. Hartwig, T. Ishiyama, and N. Miyaura Tetrahedron Lett. 43 2002 5649 5651
78. P. Harrison, J. Morris, P.G. Steel, and T.B. Marder Synlett 2009 147 150
79. P. Harrison, J. Morris, T.B. Marder, and P.G. Steel Org. Lett. 11 2009 3586 3589
80. G.A. Chotana, M.A. Rak, and M.R. Smith III J. Am. Chem. Soc. 127 2005 10539 10544
81. J.M. Murphy, X. Liao, and J.F. Hartwig J. Am. Chem. Soc. 129 2007 15434 15435
82. N.D.P. Cosford, L. Bleicher, A. Herbaut, J.S. McCallum, J.-M. Vernier, H. Dawson, J.P. Whitten, P. Adams, L. Chavez-Noriega, L.D. Correa, J.H. Crona, L.S. Mahaffy, F. Menzaghi, T.S. Rao, R. Reid, A.I. Sacaan, E. Santori, K.A. Stauderman, K. Whelan, G.K. Lloyd, and I.A. McDonald J. Med. Chem. 39 1996 3235 3237
83. F.F. Wagner, and D.L. Comins J. Org. Chem. 71 2006 8673 8675
84. M.A. Larsen, and J.F. Hartwig J. Am. Chem. Soc. 136 2014 4287 4299
85. M. Wasa, B.T. Worrell, and J.-Q. Yu Angew. Chem. 122 2010 1297 1299
86. Angew. Chem., Int. Ed. 2010, 49, 1275-1277
87. T.E. Hurst, T.K. Macklin, M. Becker, E. Hartmann, W. Kügel, J.-C. Parisienne-La Salle, A.S. Batsanov, T.B. Marder, and V. Snieckus Chem. - Eur. J. 16 2010 8155 8161
88. E.J.-G. Anctil, and V. Snieckus A. de Meijere, F. Diederich, Metal-catalyzed Cross-coupling Reactions 2004 Wiley-VCH Weinheim, Germany 761 814
89. M.C. Whisler, S. MacNeil, V. Snieckus, and P. Beak Angew. Chem. 116 2004 2256 2276
90. Angew. Chem., Int. Ed. 2004, 43, 2206-2225
91. C.G. Hartung, and V. Snieckus D. Astruc, Modern Arene Chemistry 2002 Wiley-VCH Weinheim, Germany 330 367
92. V. Snieckus Chem. Rev. 90 1990 879 933
93. see M. Alessi, A.L. Larkin, K.A. Ogilvie, L.A. Green, S. Lai, S. Lopez, and V. Snieckus J. Org. Chem. 72 2007 1588 1594
94. D.F. Fischer, and R. Sarpong J. Am. Chem. Soc. 132 2010 5926 5927
95. T. Ishiyama, J. Takagi, K. Ishida, N. Miyaura, N.R. Anastasi, and J.F. Hartwig J. Am. Chem. Soc. 124 2001 390 391
96. J.-Y. Cho, M.K. Tse, D. Holmes, R.E. Maleczka, and M.R. Smith III Science 295 2002 305 308
97. B.-J. Li, and Z.-J. Shi Chem. Sci. 2 2011 488 493
98. M. Ye, G.-L. Gao, and J.-Q. Yu J. Am. Chem. Soc. 133 2011 6964 6967
99. see: X. Cong, H. Tang, C. Wu, and X. Zeng Organometallics 32 2013 6565 6575
100. J.V. Quagliano, and L. Schubert Chem. Rev. 50 1952 201 260
101. B.J. Coe, and S.J. Glenwright Coord. Chem. Rev. 203 2000 5 80
102. P. Guo, J.M. Joo, S. Rakshit, and D. Sames J. Am. Chem. Soc. 133 2011 16338 16341
103. M. Ye, G.-L. Gao, A.J.F. Edmunds, P.A. Worthington, J.A. Morris, and J.-Q. Yu J. Am. Chem. Soc. 133 2011 19090 19093
104. see: F. Dai, Q. Gui, J. Liu, Z. Yang, X. Chen, R. Guo, and Z. Tan Chem. Commun. 2013 4634 4636
105. M. Gómez, J. Granell, and M. Martinez Organometallics 16 1997 2539 2546
106. M. Gómez, J. Granell, and M. Martinez Chem. Soc., Dalton Trans. 1998 3737 3744
107. D.L. Davies, S.M.A. Donald, and S.A. Macgregor J. Am. Chem. Soc. 127 2005 13754 13755
108. K.M. Engle, D.-H. Wang, and J.-Q. Yu J. Am. Chem. Soc. 132 2010 1413-14151
109. M.-Y. Chang, R.-T. Hsu, H.-P. Chen, and P.-J. Lin Heterocycles 68 2006 1173 1183
110. M. Macchia, L. Cervetto, G.C. Demontis, B. Longoni, F. Minutolo, E. Orlandini, G. Ortore, C. Papi, A. Sbrana, and B. Macchia J. Med. Chem. 46 2003 161 168
111. M. Amat, M. Cantó, N. Llor, C. Escolano, E. Molins, E. Espinosa, and J. Bosch J. Org. Chem. 67 2002 5343 5351
112. Y. Alhara, and N. Chatani Chem. Sci. 4 2013 664 670
113. J. Zhou, B. Li, and B.-F. Shi Org. Lett. 15 2013 3460 3463
114. F.W. Patureau, and F.J. Glorius J. Am. Chem. Soc. 132 2010 9982 9983
115. see: Alemparte-Gallardo, C.; Barros-Aguirre, D.; Cacho-Izquierdo, M.; Fiandor-Roman, J. M.; Remuinan-Blanco, M. J. WO. Patent No. 2009/141399b, 2009.
116. see: M.A. Seefeld, W.H. Miller, K.A. Newlander, W.J. Burgess, W.E. DeWolf Jr., P.A. Elkins, M.S. Head, D.R. Jakas, C.A. Janson, P.M. Keller, P.J. Manley, T.D. Moore, D.J. Payne, S. Pearson, B.J. Polizzi, X. Qiu, S.F. Rittenhouse, I.N. Uzinskas, N.G. Wallis, and W.F. Huffman J. Med. Chem. 46 2003 1627 1635
117. M. Nishino, K. Hirano, T. Satoh, and M. Miura Angew. Chem. 125 2013 13213 13217
118. Angew. Chem., Int. Ed. 2013, 52, 4457-4461
119. see: S. Ranjit, R. Lee, D. Heryadi, C. Shen, J. Wu, P. Zhang, K.-W. Huang, and X. Liu J. Org. Chem. 76 2011 8999 9007
120. T. Truong, K. Klimovica, and O. Daugulis J. Am. Chem. Soc. 135 2013 9342 9345
121. J. Roane, and O. Daugulis Org. Lett. 15 2013 5842 5845
122. L.D. Tran, J. Roane, and O. Daugulis Angew. Chem. 125 2013 6159 6162
123. Angew. Chem., Int. Ed. 2013, 52, 6043-6046
124. Y. Shang, X. Jie, H. Zhao, P. Hu, and W. Su Org. Lett. 16 2013 416 419
125. N. Guimond, C. Gouliaras, and K. Fagnou J. Am. Chem. Soc. 132 2010 6908 6909
126. D.R. Stuart, P. Alsabeh, M. Kuhn, and K. Fagnou J. Am. Chem. Soc. 132 2010 18326 18339
127. A.S. Tsai, M.E. Tauchert, R.G. Bergman, and J.A. Ellman J. Am. Chem. Soc. 133 2011 1248 1250
128. Z.-C. Qian, J. Zhou, B. Li, F. Hu, and B.-F. Shi Org. Biomol. Chem. 12 2014 3594 3597
129. K.S. Kanyiva, Y. Nakao, and T. Hiyama Angew. Chem. 119 2007 9028 9030
130. Angew. Chem., Int. Ed. 2007, 46, 8872-8874
131. C.-C. Tsai, W.-C. Shih, C.-H. Fang, C.-Y. Li, T.-G. Ong, and G.P.A. Yap J. Am. Chem. Soc. 132 2010 11887 11889
132. Y. Nakao, Y. Yamada, N. Kashihara, and T. Hiyama J. Am. Chem. Soc. 132 2010 13666 13668
133. J. Zhou, B. Li, Z.-C. Qian, and B.-F. Shi Adv. Synth. Catal. 356 2014 1038 1046
134. C. Cheng, and J.F. Hartwig Science 343 2014 853 857
135. C. Cheng, and J.F. Hartwig J. Am. Chem. Soc. 137 2015 592 595
136. L.-B. Zhang, X.-Q. Hao, S.-K. Zhang, K. Liu, B. Ren, J.-F. Gong, J.-L. Niu, and M.-P. Song J. Org. Chem. 79 2014 10399 10409
137. X.-Q. Hao, L.-J. Chen, B. Ren, L.-Y. Li, X.-Y. Yang, J.-F. Gong, J.-L. Niu, and M.-P. Song Org. Lett. 16 2014 1104 1107
138. M. Shang, S.-Z. Sun, H.-X. Dai, and J.-Q. Yu J. Am. Chem. Soc. 136 2014 3354 3357
139. see: D. Shabashov, and O. Daugulis J. Am. Chem. Soc. 132 2010 3965 3972
140. R. Giri, N.L. Maugel, B.M. Foxman, and J.-Q. Yu Organometallics 27 2008 1667 1670
141. M. Shang, H.-L. Wang, S.-Z. Sun, H.-X. Dai, and J.-Q. Yu J. Am. Chem. Soc. 136 2014 11590 11593
142. M. Shang, S.-Z. Sun, H.-L. Wang, B.N. Laforteza, H.-X. Dai, and J.-Q. Yu Angew. Chem. 126 2014 10607 10610
143. Angew. Chem., Int. Ed. 2014, 53, 10439-10442
144. M. Shang, S.-Z. Sun, H.-X. Dai, and J.-Q. Yu Org. Lett. 16 2014 5666 5669
145. D. Katayev, K.F. Pfister, T. Wendling, and L.J. Gooßen Chem. - Eur. J. 20 2014 9902 9905
146. O. Daugulis, and V.G. Zaitsev Angew. Chem. 117 2005 4114 4116
147. Angew. Chem., Int. Ed. 2005, 44, 4046-4048
148. see: L.J. Gooßen, N. Rodriguez, F. Manjolinho, and P.P. Lange Adv. Synth. Catal. 352 2010 2913 2917
149. see: L. Zhang, Z. Liu, H. Li, G. Fang, B.-D. Barry, T.A. Belay, X. Bi, and Q. Liu Org. Lett. 13 2011 6536 6539
150. X. Ribas, D.A. Jackson, B. Donnadie, J. Mahía, T. Parella, R. Xifra, B. Hedman, K.O. Hodgson, A. Llobet, and T.D.P. Stack Angew. Chem. 114 2002 3117 3120
151. Angew. Chem., Int. Ed. 2002, 130, 2991-2994
152. A.E. King, L.M. Huffman, A. Casitas, M. Costas, X. Ribas, and S.S. Stahl J. Am. Chem. Soc. 132 2010 12068 12073
153. L.M. Huffman, and S.S. Stahl J. Am. Chem. Soc. 130 2008 9196 9197
154. A.M. Suess, M.Z. Ertem, C.J. Cramer, and S.S. Stahl J. Am. Chem. Soc. 135 2013 9797 9804
155. X. Li, Y.-H. Liu, W.-J. Gu, B. Li, F.-J. Chen, and B.-F. Shi Org. Lett. 16 2014 3904 3907
156. Z.-L. Wang, L. Zhao, and M.-X. Wang Org. Lett. 13 2011 6560 6563
157. Y.-J. Liu, Y.-H. Liu, X.-S. Yin, W.-J. Gu, and B.-F. Shi Chem. - Eur. J. 21 2015 205 209
158. X.-S. Yin, Y.-C. Li, J. Yan, W.-J. Gu, and B.-F. Shi Org. Chem. Front. 2 2015 119 123
159. R. Grigg, and V. Savic Tetrahedron Lett. 38 1997 5737 5740
160. J.-Y. Cho, C.N. Iverson, and M.R. Smith III J. Am. Chem. Soc. 122 2000 12868 12869
161. R.E. Maleczka, F. Shi, D. Holmes, and M.R. Smith III J. Am. Chem. Soc. 125 2003 7792 7793
162. T. Tagata, and M. Nishida Adv. Synth. Catal. 346 2004 1655 1660
163. see: H. Tajuddin, L. Shukla, A.C. Maxwell, T.B. Marder, and P.G. Steel Org. Lett. 12 2010 5700 5703
164. I.A.I. Mkhalid, D.N. Coventry, D. Albesa-Jove, A.S. Batsanov, J.A.K. Howard, R.N. Perutz, and T.B. Marder Angew. Chem. 118 2006 503 505
165. Angew. Chem., Int. Ed. 2006, 45, 489-491
166. S.M. Preshlock, D.L. Plattner, P.E. Maligres, S.W. Krska, R.E. Maleczka, and M.R. Smith III Angew. Chem. 125 2013 13153 13157
167. Angew. Chem., Int. Ed. 2013, 52, 12915-12919
168. P.C. Roosen, V.A. Kallepalli, B. Chattopadhyay, D.A. Singleton, R.E. Maleczka Jr., and M.R. Smith III J. Am. Chem. Soc. 134 2012 11350 11353
169. M. Lafrance, D. Shore, and K. Fagnou Org. Lett. 8 2006 5097 5100
170. M. Lafrance, C.N. Rowley, T.K. Woo, and K. Fagnou J. Am. Chem. Soc. 128 2006 8754 8756
171. H.-Q. Do, and O. Daugulis J. Am. Chem. Soc. 130 2008 1128 1129
172. Y. Wie, J. Kann, M. Wang, W. Su, and M. Hong Org. Lett. 11 2009 3346 3349
173. X. Zhang, S. Fan, C.-Y. He, X. Wan, Q.-Q. Min, J. Yang, and Z.-X. Jiang J. Am. Chem. Soc. 132 2010 4506 4507
174. C.-Y. He, S. Fan, and X. Zhang J. Am. Chem. Soc. 132 2010 12850 12852
175. Y. Wei, H. Zaho, J. Kan, W. Su, and M. Hong J. Am. Chem. Soc. 132 2010 2522 2523
176. Y. Wei, and W. Su J. Am. Chem. Soc. 132 2010 16377 16379
177. H.-Q. Do, and O. Daugulis J. Am. Chem. Soc. 133 2011 13577 13586
178. K. Oshima, T. Ohmura, and M. Suginome J. Am. Chem. Soc. 133 2011 7324 7327
179. see: T. Sagawa, Y. Asano, and F. Ozawa Organometallics 21 2002 5879 5886
180. see: Onozawa, S.; Tanaka, M. Organometallics, 2001, 20, 2956-2958
181. G. Mann, K.D. John, and R.T. Baker Org. Lett. 2 2000 2105 2108
182. S. Ueno, N. Chatani, and F. Kakiuchi J. Am. Chem. Soc. 129 2007 6098 6099
183. T. Ohmura, K. Masuda, I. Takase, and M. Suginome J. Am. Chem. Soc. 131 2009 1624 1625
184. K. Masuda, T. Ohmura, and M. Suginome Organometallics 30 2011 1322 1325
185. L.D. Tran, I. Popov, and O. Daugulis J. Am. Chem. Soc. 134 2012 18237 18240
186. O. Reinaud, P. Capdevielle, and M. Maumy J. Am. Chem. Soc. Commun. 1990 566 568
187. X.-C. Wang, Y. Hu, S. Bonacorsi, Y. Hong, R. Burrell, and J.-Q. Yu J. Am. Chem. Soc. 135 2013 10326 10329
188. Y. Nakao, N. Kashihara, K.S. Kanyiva, and T. Hiyama J. Am. Chem. Soc. 130 2008 16170 16171
189. W.-Y. Huang, and J.-T. Liu J. Fluorine Chem. 71 1995 51 54
190. W.-Y. Huang, and Y. Xie Chin. J. Chem. 1990 362 369
191. W.-Y. Huang, and L. Lu Chin. J. Chem. 1992 365 372
192. W.-Y. Huang, and Y. Xie Chin. J. Chem. 1990 536 541
193. W.-Y. Huang, and J.-T. Liu Chin. J. Chem. 1991 347 348
194. T. Kino, Y. Nagase, Y. Ohtsuka, K. Yamamoto, D. Uraguchi, K. Tokuhisa, and T. Yamakawa J. Fluorine Chem. 131 2010 98 105
195. D. Uraguchi, K. Yamamoto, Y. Otsuka, K. Tokuhisa, and T. Yamakawa Appl. Catal. A Gen. 342 2008 137 143
196. F. Minisci, E. Vismara, and F. Fontana J. Org. Chem. 49 1989 345 356
197. J.M. Hoover, B.L. Ryland, and S.S. Stahl J. Am. Chem. Soc. 135 2013 2357 2367
198. X. Cong, and X. Zeng Org. Lett. 16 2014 3716 3719
199. Z. Dong, and G. Dong J. Am. Chem. Soc. 135 2013 18350 18353
200. J. Kwak, M. Kim, and S. Chang J. Am. Chem. Soc. 133 2011 3780 3783
201. S.J. Hwang, S.H. Cho, and S. Chang J. Am. Chem. Soc. 130 2008 16158 16159
202. E.J. Park, S.H. Kim, and S. Chang J. Am. Chem. Soc. 130 2008 17268 17269
203. S.H. Cho, J.Y. Kim, S.Y. Lee, and S. Chang Angew. Chem. 121 2009 9291 9294
204. Angew. Chem., Int. Ed. 2009, 48, 9172-9130
205. J.Y. Kim, S.H. Cho, J. Joseph, and S. Chang Angew. Chem. 122 2010 10095 10099
206. Angew. Chem., Int. Ed. 2010, 49, 9899-9903
207. J. Kim, and S. Chang J. Am. Chem. Soc. 132 2010 10272 10274
208. S.H. Kim, and S. Chang Org. Lett. 12 2010 1868 1871
209. A.R. Chakravarty, F.A. Cotton, D.A. Tocher, and J.H. Tocher Organometallics 4 1995 8 13
210. T. Fukuyama, N. Chatani, J. Tatsumi, F. Kakiuchi, and S. Muraji J. Am. Chem. Soc. 120 1998 11522 11523
211. S.E. Kabir, D.S. Kolwaite, E. Rosenberg, K. Hardcastle, W. Cressell, and J. Grindstaff Organometallics 14 1995 3611 3613
212. J.R. Shapley, D.E. Samkoff, C. Bueno, and M.R. Churchill Inorg. Chem. 21 1982 634 639
213. S. Konishi, S. Kawamorita, T. Iwai, P.G. Steel, T.B. Marder, and M. Sawamura Chem. - Asian. J. 9 2014 434 438
214. Y. Zhang, J. Gao, W. Li, H. Lee, B.Z. Lu, and C.H. Senanayaka J. Org. Chem. 76 2011 6394 6400
215. see: Y. Abe, H. Kayakiri, S. Satoh, T. Inoue, Y. Sawada, N. Inamura, M. Asano, I. Armori, C. Hatori, H. Sawai, T. Oku, and H. Tanka J. Med. Chem. 41 1998 4062 4079
216. T. Shibata, and Y. Matsuo Adv. Synth. Catal. 356 2014 1516 1520
217. C. Coperet, H. Adolfsson, T.-A.W. Khuong, A.K. Yudin, and K.B. Sharpless J. Org. Chem. 63 1998 1740 1741
218. O.V. Larionov, D. Stephens, A.M. Mfuh, H.D. Arman, A.S. Naumova, G. Chavez, and B. Skenderi Org. Biomol. Chem. 12 2014 3026 3036
219. H. Hwang, J. Kim, and S. Chang J. Am. Chem. Soc. 136 2014 10770 10776
220. L. Mao, T. Moriuchi, H. Sakurai, H. Fujii, and T. Hirao Tetrahedron Lett. 46 2005 8419 8422
221. C.-I. Lee, J. Zhou, and O. Ozerov J. Am. Chem. Soc. 135 2013 3560 3566
222. I.E. Nifant'ev, P.V. Ivchenko, V.V. Bagrov, S.M. Nagy, L.N. Winslow, J.A. Merrick-Mack, S. Mihan, and A.V. Churakov Dalton Trans. 42 2013 1501 1511
223. E.M. Simmons, and J.F. Hartwig Angew. Chem. 124 2012 3120 3126
224. Angew. Chem., Int. Ed. 2012, 51, 3066-3072
225. C.J. Fahrni, and T.V. O'Halloran J. Am. Chem. Soc. 121 1999 11448 11458
226. M.C. Kimber, I.B. Mahadevan, S.F. Lincoln, A.D. Ward, and E.R.T. Tiekink J. Org. Chem. 65 2000 8204 8209
227. J. Jeong, P. Patel, H. Hwang, and S. Chang Org. Lett. 16 2014 4598 4601
228. C. Feng, and T.-P. Loh Angew. Chem. 126 2014 2760 2764
229. Angew. Chem. Int. Ed. 2014, 53, 2722-2726
230. F. Xie, Z. Qi, S. Yu, and X. Li J. Am. Chem. Soc. 136 2014 4780 4787
231. K.D. Collins, F. Lied, and F. Glorius Chem. Commun. 2014 4459 4461
232. C. Feng, D. Feng, and T.-P. Loh Chem. Commun. 2014 9865 9868
233. X. Zhang, Z. Qui, and X. Li Angew. Chem. 126 2014 10970 10974
234. Angew. Chem., Int. Ed. 2014, 53, 10794-10798
235. Y. Li, S. Liu, Z. Qi, X. Qi, X. Li, and Y. Lan Chem. - Eur. J. 21 2015 10131 10137
236. R. Peverati, and D.G. Truhlar J. Phys. Chem. Lett. 3 2012 117 124
237. U. Sharma, Y. Park, and S. Chang J. Org. Chem. 79 2014 9899 9906
238. D.E. Stephens, J. Lakey-Beitia, A.C. Atesin, T.A. Atesin, G. Chavez, H.D. Arman, and O.V. Larionov ACS Catal. 5 2015 167 175
239. K. Shin, S.-W. Park, and S. Chang J. Am. Chem. Soc. 137 2015 8584 8592
240. D.E. Stephens, J. Lakey-Beitia, G. Chavez, C. Illie, H.D. Arman, and O.V. Larionov Chem. Commun. 2015 9507 9510
241. N.S. Akhmadullina, N.V. Cherkashina, N.Y. Kozitsyna, I.P. Stolarov, E.V. Perova, A.E. Gekhman, S.E. Nefedov, M.N. Vargaftik, and I.I. Moiseev Inorg. Chim. Acta 362 2009 1943 1951
242. L.A. Adrio, B.N. Nguyen, G. Guilera, A.G. Livingston, and K.K. Hii Catal. Sci. Technol. 2 2012 316 323
243. S. Yu, B. Wan, and X. Li Org. Lett. 17 2015 58 61
244. C. Grohmann, H.-G. Wang, and F. Glorius Org. Lett. 15 2013 3014 3017
245. N. Schroder, J. Wencel-Delord, and F. Glorius J. Am. Chem. Soc. 134 2012 8298 8301
246. S. Yu, B. Wan, and X. Li Org. Lett. 15 2013 3706 3709
247. J. Wencel-Delord, C. Nimphius, F.W. Patureau, and F. Glorius Angew. Chem. 124 2012 2290 2294
248. Angew. Chem., Int. Ed. 2012, 51, 2247-2251