Transition-Metal-Catalyzed Direct Addition of Aryl C–H Bonds to Unsaturated Electrophiles

Chemical Record

Volumn , Issue , 2016, Pages 1178-1190

  Shi, Xian Ying ^a   Han, Wen Jing ^a   Li, Chao Jun ^b  

^a Key Laboratory of Applied Surface and Colloid Chemistry (Ministry of Education)   (China)

^b MCGILL UNIVERSITY   (Canada)

Author keywords

1,2 addition; conjugate addition; C H activation; homogeneous catalysis; tandem reactions

Indexed keywords

EID: 84974822378     PISSN: 15278999     EISSN: 15280691     Source Type: Journal    
DOI: 10.1002/tcr.201500250     Document Type: Article

References (239)

1. For reviews on C–H functionalization, see:
2. V. Ritleng, C. Sirlin, M. Pfeffer, Chem. Rev. 2002, 102, 1731–1769;
3. C. Jia, T. Kitamura, Y. Fujiwara, Acc. Chem. Res. 2001, 34, 633–639;
4. X. Chen, K. M. Engle, D. H. Wang, J. Q. Yu, Angew. Chem. 2009, 121, 5196–5207.
5. Angew. Chem. Int. Ed. 2009, 48, 5094–5115;
6. M. S. Sigman, E. W. Werner, Acc. Chem. Res. 2012, 45, 874–884;
7. B. G. Hashiguchi, S. M. Bischof, M. M. Konnick, R. A. Periana, Acc. Chem. Res. 2012, 45, 885–898;
8. S. R. Neufeldt, M. S. Sanford, Acc. Chem. Res. 2012, 45, 936–946;
9. O. Daugulis, H.-Q. Do, D. Shabashov, Acc. Chem. Res. 2009, 42, 1074–1086;
10. K. M. Engle, T.-S. Mei, M. Wasa, J.-Q. Yu, Acc. Chem. Res. 2012, 45, 788–802;
11. K. Gao, N. Yoshikai, Acc. Chem. Res. 2014, 47, 1208–1219;
12. X.-F. Wu, Chem. Eur. J. 2015, 21, 12252–12265;
13. C. I. Herrerías, X. Yao, Z. Li, C.-J. Li, Chem. Rev. 2007, 107, 2546–2562;
14. P. B. Arockiam, C. Bruneau, P. H. Dixneuf, Chem. Rev. 2012, 112, 5879–5918;
15. F. Bellina, R. Rossi, Chem. Rev. 2010, 110, 1082–1146;
16. P. L. Arnold, M. W. McMullon, J. Rieb, F. E. Kühn, Angew. Chem. 2015, 127, 84–103.
17. Angew. Chem. Int. Ed. 2015, 54, 82–100;
18. D.-G. Yu, B.-J. Li, Z.-J. Shi, Tetrahedron 2012, 68, 5130–5136;
19. R. He, Z.-T. Huang, Q.-Y. Zheng, C. Wang, Tetrahedron Lett. 2014, 55, 5705–5713;
20. S. A. Girard, T. Knauber, C.-J. Li, Angew. Chem. 2014, 126, 76–103.
21. Angew. Chem. Int. Ed. 2014, 53, 74–100;
22. J. Yang, Org. Biomol. Chem. 2015, 13, 1930–1941;
23. B. Li, P. H. Dixneuf, Chem. Soc. Rev. 2013, 42, 5744–5767;
24. V. S. Thirunavukkarasu, S. I. Kozhushkov, L. Ackermann, Chem. Commun. 2014, 50, 29–39;
25. C. Copéret, Chem. Rev. 2010, 110, 656–680;
26. S. H. Cho, J. Y. Kim, J. Kwak, S. Chang, Chem. Soc. Rev. 2011, 40, 5068–5083;
27. J. Wencel-Delord, T. Dröge, F. Liu, F. Glorius, Chem. Soc. Rev. 2011, 40, 4740–4761;
28. C. S. Yeung, V. M. Dong, Chem. Rev. 2011, 111, 1215–1292.
29. S. Murai, F. Kakiuchi, S. Sekine, Y. Tanaka, A. Kamatani, M. Sonoda, N. Chatani, Nature 1993, 366, 529–531;
30. N. Chatani, T. Uemura, T. Asaumi, Y. Ie, F. Kakiuchi, S. Murai, Can. J. Chem. 2005, 83, 755–763;
31. F. Kakiuchi, M. Matsumoto, K. Tsuchiya, K. Igi, T. Hayamizu, N. Chatani, S. Murai, J. Organomet. Chem. 2003, 686, 134–144;
32. F. Kakiuchi, M. Matsumoto, K. Tsuchiya, K. Igi, T. Asaumi, N. Chatani, T. Matsuo, F. Kakiuchi, S. Murai, J. Org. Chem. 2003, 68, 7538–7540;
33. F. Kakiuchi, S. Kan, K. Igi, N. Chatani, S. Murai, J. Am. Chem. Soc. 2003, 125, 1698–1699;
34. N. Chatani, S. Yorimitsu, T. Asaumi, F. Kakiuchi, S. Murai, J. Org. Chem. 2002, 67, 7557–7560;
35. N. Chatani, A. Kamitani, S. Murai, J. Org. Chem. 2002, 67, 7014–7018;
36. Y. Fukumoto, K. Sawada, M. Hagihara, N. Chatani, S. Murai, Angew. Chem. 2002, 114, 2903–2905.
37. Angew. Chem. Int. Ed. 2002, 41, 2779–2781;
38. Y. Fukumoto, T. Dohi, H. Masaoka, N. Chatani, S. Murai, Organometallics 2002, 21, 3845–3847;
39. F. Kakiuchi, S. Murai, Acc. Chem. Res. 2002, 35, 826–834;
40. N. Chatani, T. Asaumi, S. Yorimitsu, T. Ikeda, F. Kakiuchi, S. Murai, J. Am. Chem. Soc. 2001, 123, 10935–10941;
41. N. Chatani, T. Asaumi, T. Ikeda, S. Yorimitsu, Y. Ishii, F. Kakiuchi, S. Murai, J. Am. Chem. Soc. 2000, 122, 12882–12883;
42. N. Chatani, T. Fukuyama, H. Tatamidani, F. Kakiuchi, S. Murai, J. Org. Chem. 2000, 65, 4039–4047;
43. Y. Ie, N. Chatani, T. Ogo, D. R. Marshall, T. Fukuyama, F. Kakiuchi, S. Murai, J. Org. Chem. 2000, 65, 1475–1488.
44. For examples, see:
45. O. Daugulis, J. Roane, L. D. Tran, Acc. Chem. Res. 2015, 48, 1053–1064;
46. O. Daugulis, H.-Q. Do, D. Shabashov, Acc. Chem. Res. 2009, 42, 1074–1086.
47. For examples, see:
48. S. Warratz, C. Kornhaaß, A. Cajaraville, B. Niepötter, D. Stalke, L. Ackermann, Angew. Chem. 2015, 127, 5604–5608.
49. S. Warratz, C. Kornhaaß, A. Cajaraville, B. Niepötter, D. Stalke, L. Ackermann, Angew. Chem. 2015, 127, 5604–5608.
50. Angew. Chem. Int. Ed. 2015, 54, 5513–5517;
51. J. Li, L. Ackermann, Chem. Eur. J. 2015, 20, 5718–5722;
52. J. Li, L. Ackermann, Angew. Chem. 2015, 127, 3706–3709.
53. Angew. Chem. Int. Ed. 2015, 54, 3635–3638;
54. F. Yang, K. Rauch, K. Kettelhoit, L. Ackermann, Angew. Chem. 2014, 126, 11467– 11470.
55. Angew. Chem. Int. Ed. 2014, 53, 11285–11288.
56. L. Ackermann, A. V. Lygin, N. Hofmann, Angew. Chem. 2011, 123, 6503–6506.
57. Angew. Chem. Int. Ed. 2011, 50, 6379–6382.
58. L. Ackermann, N. Hofmann, R. Vicente, Org. Lett. 2011, 13, 1875–1877.
59. For examples, see:
60. K. M. Engle, N. Dastbaravardeh, P. S. Thuy-Boun, D. H. Wang, A. C. Sather, J.-Q. Yu, Org. Synth. 2015, 92, 58–75;
61. G. Li, L. Wan, G. Zhang, D. Leow, J. Spangler, J.-Q. Yu, J. Am. Chem. Soc. 2015, 137, 4391–4397;
62. Y. Lu, H.-W. Wang, J. E. Spangler, K. Chen, P.-P. Cui, Y. Zhao, W.-Y. Sun, J.-Q. Yu, Chem. Sci. 2015, 6, 1923– 1927;
63. D. Zhu, G. Yang, J. He, L. Chu, G. Chen, W. Gong, K. Chen, M. D. Eastgate, J.-Q. Yu, Angew. Chem. 2015, 127, 2327– 2340.
64. Angew. Chem. Int. Ed. 2015, 54, 2497–2500;
65. E. J. Yoo, S. Ma, T.-S. Mei, K. S. L. Chan, J.-Q. Yu, J. Am. Chem. Soc. 2011, 133, 7652–7655;
66. X. Wang, L. Truesdale, J.-Q. Yu, J. Am. Chem. Soc. 2010, 132, 3648–3649;
67. R. Giri, J. K. Lam, J-.Q. Yu, J. Am. Chem. Soc. 2010, 132, 686–693;
68. M. Wasa, B. T. Worrell, J.-Q. Yu, Angew. Chem. 2010, 122, 1297–1299.
69. Angew. Chem. Int. Ed. 2010, 49, 1275–1277;
70. D.-H. Wang, T.-S. Mei, J.-Q. Yu, J. Am. Chem. Soc. 2008, 130, 17676–17677.
71. For examples, see:
72. X. Wang, D.-G. Yu, F. Glorius, Angew. Chem. 2015, 127, 10419–10422;
73. Angew. Chem. Int. Ed. 2015, 54, 10280–10283.
74. N. Schröder, F. Lied, F. Glorius, J. Am. Chem. Soc. 2015, 137, 1448–1451;
75. D. Zhao, J. H. Kim, L. Stegemann, C. A. Strassert, F. Glorius, Angew. Chem. 2015, 127, 4591–4594.
76. Angew. Chem. Int. Ed. 2015, 54, 4508–4511;
77. D. Zhao, S. Vásquez-Céspedes, F. Glorius, Angew. Chem. 2015, 127, 1677–1681.
78. Angew. Chem. Int. Ed. 2015, 54, 1657–1661;
79. D.-G. Yu, T. Gensch, F. de Azambuja, S. Vásquez-Céspedes, F. Glorius, J. Am. Chem. Soc. 2014, 136, 17722–17725;
80. H. Wang, N. Schröder, F. Glorius, Angew. Chem. 2013, 125, 5495–5499; Angew. Chem. Int. Ed. 2013, 52, 5386–5389.
81. Angew. Chem. Int. Ed. 2013, 52, 5386–5389.
82. For examples, see:
83. A. S. Tsai, M. E. Tauchert, R. G. Bergman, J. A. Ellman, J. Am. Chem. Soc. 2011, 133, 1248–1250;
84. M. Brasse, J. Cámpora, J. A. Ellman, R. G. Bergman, J. Am. Chem. Soc. 2013, 135, 6427–6430;
85. Y. Lian, R. G. Bergman, L. D. Lavis, J. A. Ellman, J. Am. Chem. Soc. 2013, 135, 7122–7125;
86. J. R. Hummel, J. A. Ellman, J. Am. Chem. Soc. 2015, 137, 490–498.
87. For examples, see:
88. J. J. Topczewski, M. S. Sanford, Chem. Sci. 2014, 6, 70–76;
89. L. J. Allen, P. J. Cabrera, M. Lee, M. S. Sanford, J. Am. Chem. Soc. 2014, 136, 5607–5610;
90. A. M. Wagner, A. J. Hickman, M. S. Sanford, J. Am. Chem. Soc. 2013, 135, 15710–15713;
91. I. A. Sanhueza, A. M. Wagner, M. S. Sanford, F. Schoenebeck, Chem. Sci. 2013, 4, 2767–2775;
92. A. Maleckis, J. W. Kampf, M. S. Sanford, J. Am. Chem. Soc. 2013, 135, 6618–6625;
93. K. J. Stowers, A. Kubota, M. S. Sanford, Chem. Sci. 2012, 3, 3192–3195;
94. J. M. Racowski, N. D. Ball, M. S. Sanford, J. Am. Chem. Soc. 2011, 133, 18022–18025.
95. For examples, see:
96. R. Zhu, J. Wei, Z. Shi, Chem. Sci. 2013, 4, 3706–3711;
97. F. Pan, Z.-Q. Lei, H. Wang, H. Li, J. Sun, Z.-J. Shi, Angew. Chem. 2013, 125, 2117–2121.
98. Angew. Chem. Int. Ed. 2013, 52, 2063–2067;
99. K. Chen, H. Li, Z.-Q. Lei, Y. Li, W.-H. Ye, L.-S. Zhang, J. Sun, Z.-J. Shi, Angew. Chem. 2012, 124, 9989–9993.
100. Angew. Chem. Int. Ed. 2012, 51, 9851–9855;
101. B.-J. Li, H.-Y. Wang, Q.-L. Zhu, Z.-J. Shi, Angew. Chem. 2012, 124, 4014–4018.
102. Angew. Chem. Int. Ed. 2012, 51, 3948–3952.
103. R.-J. Tang, C.-P. Luo, L. Yang, C.-J. Li, Adv. Synth. Catal . 2013, 355, 869–873;
104. M. Sun, L.-K. Hou, X.-X. Chen, X.-J. Yang, W. Sun, Y.-S. Zang, Adv. Synth. Catal. 2014, 356, 3789–3793;
105. K. Padala, M. Jeganmohan, Chem. Eur. J. 2014, 20, 4092–4097;
106. R. B. Dateer, S. Chang, J. Am. Chem. Soc. 2015, 137, 4908–4911;
107. H. Hwang, J. Kim, J. Jeong, S. Chang, J. Am. Chem. Soc. 2014, 136, 10770–10776;
108. J. Kim, S. Chang, Angew. Chem. 2014, 126, 2235–2239.
109. Angew. Chem. Int. Ed. 2014, 53, 2203–2207;
110. J. Ryu, J. Kwak, K. Shin, D. Lee, S. Chang, J. Am. Chem. Soc. 2013, 135, 12861–12868;
111. K. Shin, Y. Baek, S. Chang, Angew. Chem. 2013, 125, 8189–8194.
112. Angew. Chem. Int. Ed. 2013, 52, 8031–8036;
113. J. Y. Kim, S. H. Park, J. Ryu, S. H. Cho, S. H. Kim, S. Chang, J. Am. Chem. Soc. 2012, 134, 9110–9113;
114. J. Kwak, Y. Ohk, Y. Jung, S. Chang, J. Am. Chem. Soc. 2012, 134, 17778–17788;
115. J. Ryu, K. Shin, S. H. Park, J. Y. Kim, S. Chang, Angew. Chem. 2012, 124, 10042– 10046.
116. Angew. Chem. Int. Ed. 2012, 51, 9904–9908;
117. Q. A. Chen, D. K. Kim, V. M. Dong, J. Am. Chem. Soc. 2014, 136, 3772–3775;
118. K. G. M. Kou, D. N. Le, V. M. Dong, J. Am. Chem. Soc. 2014, 136, 9471–9476;
119. S. K. Murphy, A. Bruch, V. M. Dong, Chem. Sci. 2015, 6, 174–179;
120. Q. A. Chen, F. A. Cruz, V. M. Dong, J. Am. Chem. Soc. 2015, 137, 3157–3160;
121. M. von Delius, C. M. Le, V. M. Dong, J. Am. Chem. Soc. 2012, 134, 15022–15032.
122. For reviews on directing-group-assisted C–H functionalization, see:
123. D. A. Colby, R. G. Bergman, J. A. Ellman, Chem. Rev. 2010, 110, 624–655;
124. M. C. Willis, Chem. Rev. 2010, 110, 725–748;
125. T. W. Lyons, M. S. Sanford, Chem. Rev. 2010, 110, 1147–1169;
126. D. A. Colby, A. S. Tsai, R. G. Bergman, J. A. Ellman, Acc. Chem. Res. 2012, 45, 814–825;
127. T. Brückl, R. D. Baxter, Y. Ishihara, P. S. Baran, Acc. Chem. Res. 2012, 45, 826–839;
128. C. Zhu, R. Wang, J. R. Falck, Chem. Asian J. 2012, 7, 1502–1514;
129. L. Ackermann, Chem. Rev. 2011, 111, 1315–1345;
130. G. Shi, Y. Zhang, Adv. Synth. Catal. 2014, 356, 1419–1442;
131. S. D. Sarkar, W. Liu, S. I. Kozhushkov, L. Ackermann, Adv. Synth. Catal. 2014, 356, 1461–1479;
132. K. Wang, F. Hu, Y. Zhang, J. Wang, Sci. China: Chem. 2015, 58, 1252–1265.
133. D. Zhao, Z. Shi, F. Glorius, Angew. Chem . 2013, 125, 12652–12656.
134. Angew. Chem. Int. Ed. 2013, 52, 12426–12429;
135. L. Ackermann, A. V. Lygin, Org. Lett. 2012, 14, 764–767;
136. G. Liu, Y. Shen, Z. Zhou, X. Lu, Angew. Chem. 2013, 125, 6149–6153.
137. Angew. Chem. Int. Ed. 2013, 52, 6033–6037;
138. J. R. Huckins, E. A. Bercot, O. R. Thiel, T.-L. Hwang, M. M. Bio, J. Am. Chem. Soc. 2013, 135, 14492–14495;
139. L. Ackermann, J. Pospech, K. Graczyk, K. Rauch, Org. Lett. 2012, 14, 930–933;
140. N. Guimond, C. Gouliaras, K. Fagnou, J. Am. Chem. Soc. 2010, 132, 6908–6909;
141. T. K. Hyster, T. Rovis, J. Am. Chem. Soc. 2010, 132, 10565–10569;
142. R. M. Martin, R. G. Bergman, J. A. Ellman, J. Org. Chem. 2012, 77, 2501–2507.
143. L. Yang, C. A. Correia, C.-J. Li, Adv. Synth. Catal . 2011, 353, 1269–1273;
144. L. Yang, C. A. Correia, C.-J. Li, Org. Biomol. Chem. 2011, 9, 7176–7179.
145. J. Li, L. Ackermann, Angew. Chem . 2015, 127, 8671–8674.
146. Angew. Chem. Int. Ed. 2015, 54, 8551–8554;
147. J. R. Hummel, J. A. Ellman, Org. Lett. 2015, 17, 2400–2403;
148. X. Geng, C. Wang, Org. Biomol. Chem. 2015, 13, 7619–7623;
149. T. Jeong, S. Han, N. K. Mishra, S. Sharma, S.-Y. Lee, J. S. Oh, J. H. Kwak, Y. H. Jung, I. S. Kim, J. Org. Chem. 2015, 80, 7243–7250;
150. A. Correa, R. Martin, J. Am. Chem. Soc. 2014, 136, 7253–7256;
151. W. Hou, B. Zhou, Y. Yang, H. Feng, Y. Li, Org. Lett. 2013, 15, 1814–1817;
152. S. Takebayashi, T. Shizuno, T. Otani, T. Shibata, Beilstein J. Org. Chem. 2012, 8, 1844–1848;
153. Y. Kuninobu, Y. Tokunaga, A. Kawata, K. Takai, J. Am. Chem. Soc. 2006, 128, 202–209;
154. K. Muralirajan, K. Parthasarathy, C.-H. Cheng, Org. Lett. 2012, 14, 4262–4265;
155. K. D. Hesp, R. G. Bergman, J. A. Ellman, J. Am. Chem. Soc. 2011, 133, 11430–11433;
156. B. Zhou, W. Hou, Y. Yang, Y. Li, Chem. Eur. J. 2013, 19, 4701–4706.
157. C.-J. Li, Acc. Chem. Res . 2010, 43, 581–590;
158. C.-J. Li, Acc. Chem. Res. 2002, 35, 533–538;
159. F. Zhou, C.-J. Li, Nat. Commun. 2014, 5, 4254–4260.
160. C. Wei, C.-J. Li, Green Chem . 2002, 4, 39–41.
161. Y. Fukumoto, K. Sawada, M. Hagihara, N. Chatani, S. Murai, Angew. Chem . 2002, 114, 2903–2905.
162. Angew. Chem. Int. Ed. 2002, 41, 2779–2781.
163. Y. Kuninobu, Y. Nishina, T. Takeuchi, K. Takai, Angew. Chem . 2007, 119, 6638–6640.
164. Angew. Chem. Int. Ed. 2007, 46, 6518–6520;
165. Y. Kuninobu, D. Asanoma, K. Takai, Synlett 2010, 2883–2886.
166. N. Kuhl, M. N. Hopkinson, J. Wencel-Delord, F. Glorius, Angew. Chem . 2012, 124, 10382–10401.
167. Angew. Chem. Int. Ed. 2012, 51, 10236–10254;
168. B.-J. Li, Z.-J. Shi, Chem. Sci. 2011, 2, 488–493;
169. X.-S. Zhang, K. Chen, Z.-J. Shi, Chem. Sci. 2014, 5, 2146–2159.
170. C.-J. Li, Y. Meng, J. Am. Chem. Soc . 2000, 122, 9538–9539.
171. X.-Y. Shi, C.-J. Li, Adv. Synth. Catal . 2012, 354, 2933–2938.
172. D. E. Games, Aromat. Heteroaromat. Chem . 1974, 2, 447–471;
173. R. D. H. Murray, Aromat. Heteroaromat. Chem. 1976, 4, 414–441;
174. S. Ghosh, I. Banerjee, S. Baul, Tetrahedron 1999, 55, 11537–11546;
175. Z. Ye, P. Qian, G. Lv, F. Luo, J. Cheng, J. Org. Chem. 2010, 75, 6043–6045.
176. S. Hayat, A. Rahman, M. I. Choudhary, K. M. Khan, E. Bayer, Tetrahedron Lett . 2001, 42, 1647–1649;
177. J. D. Hall, N. W. Duncan-Gould, N. A. Siddiqi, J. N. Kelly, L. A. Hoeferlin, S. J. Morrison, J. K. Wyatt, Bioorg. Med. Chem. 2005, 13, 1409–1413;
178. R. Pedrosa, S. Sayalero, M. Vicente, Tetrahedron 2006, 62, 10400–10407;
179. N. O. Mahmoodi, M. Salehpour, J. Heterocycl. Chem. 2003, 40, 875–878;
180. H. Zhang, S. Zhang, L. Liu, G. Luo, W. Duan, W. Wang, J. Org. Chem. 2010, 75, 368–374.
181. C. J. Li, B. M. Trost, Proc. Natl. Acad. Sci. U.S.A . 2008, 105, 13197–13202.
182. X.-Y. Shi, R. Andrea, K. Soumen, C.-J. Li, Adv. Synth. Catal . 2014, 356, 723–728.
183. X. Collin, J. Robert, G. Wielgosz, G. Le Baut, C. Bobin-Dubigeon, N. Grimaud, J. Petit, Eur. J. Med. Chem . 2001, 36, 639–649;
184. H. Teisseire, G. Vernet, Pestic. Biochem. Physiol. 2001, 69, 112–117;
185. F. B. Miguel, D. Gema, S. Beatriz, R. Cynthia, R. Simmon, B. Teresa, Eur. J. Med. Chem. 2002, 37, 541–551;
186. A. A. Abdel-Hafez, Arch. Pharmacal Res. 2004, 27, 495–501;
187. C. Shinji, T. Nakamura, S. Maeda, M. Yoshida, Y. Hashimoto, H. Miyachi, Bioorg. Med. Chem. Lett. 2005, 15, 4427–4431;
188. U. Sharma, P. Kumar, N. Kumar, B. Singh, Mini-Rev. Med. Chem. 2010, 10, 678–704.
189. T. Han, C. F. Chen, J. Org. Chem . 2007, 72, 7287–7293;
190. A. A. M. Abdel-Aziz, Eur. J. Med. Chem. 2007, 42, 614–626;
191. Z.-G. Le, Z.-C. Chen, Y. Hu, Q.-G. Zheng, J. Heterocycl. Chem. 2005, 42, 735–737;
192. C. J. Perry, Z. Parveen, J. Chem. Soc., Perkin Trans. 2 2001, 512–521.
193. X.-F. Dong, J. Fan, X.-Y. Shi, K.-Y. Liu, P.-M. Wang, J.-F. Wei, J. Organomet. Chem . 2015, 779, 55–61.
194. L. Ackermann, Acc. Chem. Res . 2014, 47, 281–295.
195. B. Li, K. Devaraj, C. Darcel, P. H. Dixneuf, Green Chem. 2012, 14, 2706–2709.
196. M. Deponti, S. I. Kozhushkov, D. S. Yufit, L. Ackermann, Org. Biomol. Chem . 2013, 11, 142–148.
197. X.-Y. Shi, K.-Y. Liu, J. Fan, X.-F. Dong, J.-F. Wei, C.-J. Li, Chem. Eur. J . 2015, 21, 1900–1903.
198. A. Maehara, H. Tsurugi, T. Satoh, M. Miura, Org. Lett . 2008, 10, 1159–1162;
199. M. Satoshi, H. Koji, S. Tetsuya, Org. Lett. 2010, 12, 5776–5779;
200. J. Cornella, M. Righi, I. Larrosa, Angew. Chem. 2011, 123, 9601–9604.
201. Angew. Chem. Int. Ed. 2011, 50, 9429–9432;
202. S. Bhadra, W. I. Dzik, L. J. Gooßen, Angew. Chem. 2013, 125, 3031–3035.
203. Angew. Chem. Int. Ed. 2013, 52, 2959–2962.
204. X.-Y. Shi, X.-F. Dong, J. Fan, K.-Y. Liu, J.-F. Wei, C.-J. Li, Sci. China: Chem . 2015, 58, 1286–1291.
205. S.-G. Lim, J.-A. Ahn, C.-H. Jun, Org. Lett . 2004, 6, 4687–4690;
206. Z.-M. Sun, J. Zhang, R. S. Manan, P. Zhao, J. Am. Chem. Soc. 2010, 132, 6935–6937;
207. Y. Kuninobu, Y. Nishina, M. Shouho, K. Takai, Angew. Chem. 2006, 118, 2832–2834.
208. Angew. Chem. Int. Ed. 2006, 45, 2766–2768;
209. L. Yang, B. Qian, H. Huang, Chem. Eur. J. 2012, 18, 9511–9515;
210. J. Ryu, S. H. Cho, S. Chang, Angew. Chem. 2012, 124, 3737–3741.
211. Angew. Chem. Int. Ed. 2012, 51, 3677–3681;
212. G. Rouquet, N. Chatani, Chem. Sci. 2013, 4, 2201–2208;
213. T. Shibata, T. Shizuno, Angew. Chem. 2014, 126, 5514–5517.
214. Angew. Chem. Int. Ed. 2014, 53, 5410–5413;
215. K. Shibata, N. Chatani, Org. Lett. 2014, 16, 5148–5151;
216. Y. Kommagalla, K. Srinivas, C. V. Ramana, Chem. Eur. J. 2014, 20, 7884–7889;
217. B. Zhou, P. Ma, H. Chen, C. Wang, Chem. Commun. 2014, 50, 14558–14561;
218. P. Duan, X. Lan, Y. Chen, S.-S. Qian, J. J. Li, L. Lu, Y. Lu, B. Chen, M. Hong, J. Zhao, Chem. Commun. 2014, 50, 12135–12138;
219. S. Pan, N. Ryu, T. Shibata, Adv. Synth. Catal. 2014, 356, 929–933.
220. X.-Y. Shi, C.-J. Li, Org. Lett . 2013, 15, 1476–1479.
221. G. Majetich, J. M. Shimkus, J. Nat. Prod . 2010, 73, 284–298;
222. N. J. Clegg, S. Paruthiyil, D. C. Leitman, T. S. Scanlan, J. Med. Chem. 2005, 48, 5989–6003;
223. E. Alcald, N. Mesquida, S. López-Pérez, J. Frigola, R. Mercè, J. Med. Chem. 2009, 52, 675–690;
224. H. G. Alt, A. Koppl, Chem. Rev. 2000, 100, 1205–1221;
225. H. Tye, S. G. Mueller, J. Prestle, S. Scheuerer, M. Schindler, B. Nosse, N. Prevost, C. J. Brown, A. Heifetz, C. Moeller, Bioorg. Med. Chem. Lett. 2011, 21, 34–37;
226. N. Nebra, N. Saffon, L. Maron, B. Martin-Vaca, D. Bourissou, Inorg. Chem. 2011, 50, 6378–6383;
227. D.-F. Chen, C.-Y. Zhang, S.-S. Xu, H.-B. Song, B.-Q. Wang, Organometallics 2011, 30, 676–683.
228. L. Yang, H. Huang, Chem. Rev . 2015, 115, 3468–3517;
229. G. Yan, X. Wu, M. Yang, Org. Biomol. Chem. 2013, 11, 5558–5578;
230. G. Qiu, Q. Ding, J. Wu, Chem. Soc. Rev. 2013, 42, 5257–5269.
231. Y. Li, B.-J. Li, W.-H. Wang, W.-P. Huang, X.-S. Zhang, K. Chen, Z.-J. Shi, Angew. Chem. 2011, 123, 2163–2167
232. Angew. Chem. Int. Ed. 2011, 50, 2115–2119
233. Y. Li, X.-S. Zhang, Q.-L. Zhu, Z.-J. Shi, Org. Lett. 2012, 14, 4498–4501;
234. Y. Li, X.-S. Zhang, K. Chen, K.-H. He, F. Pan, B.-J. Li, Z.-J. Shi, Org. Lett. 2012, 14, 636–639;
235. A. Wangweerawong, J. R. Hummel, R. G. Bergman, J. A. Ellman, J. Org. Chem. 2016, 81, 1547–1557
236. J. A. Boerth, J. A. Ellman, Chem. Sci. 2016, 7, 1474–1479
237. A. Wangweerawong, R. G. Bergman, J. A. Ellman, J. Am. Chem. Soc. 2014, 136, 8520–8523
238. K. D. Hesp, R. G. Bergman, J. A. Ellman, Org. Lett. 2012, 14, 2304–2307
239. M. E. Tauchert, C. D. Incarvito, A. L. Rheingold, R. G. Bergman, J. A. Ellman, J. Am. Chem. Soc. 2012, 134, 1482–1485