Development of direct aromatic coupling reactions by transition-metal catalysis

Bulletin of the Chemical Society of Japan

Volumn 87, Issue 7, 2014, Pages 751-764

  Miura, Masahiro ^a   Satoh, Tetsuya ^a   Hirano, Koji ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIZATION; CATALYSIS; TRANSITION METALS;

AROMATIC COUPLING; AROMATIC SUBSTRATES; CONVENTIONAL METHODS; COUPLING REACTION; CROSS COUPLING REACTIONS; ORGANIC FINE CHEMICALS; TRANSFORMATION REACTIONS; TRANSITION-METAL CATALYSIS;

AROMATIC COMPOUNDS;

EID: 84904433566     PISSN: 00092673     EISSN: 13480634     Source Type: Journal    
DOI: 10.1246/bcsj.20140099     Document Type: Article

References (186)

1. Metal-Catalyzed Cross-Coupling Reactions and More, ed. by A. de Meijere, S. Bräse, M. Oestreich, Wiley-VCH, Weinheim, 2014. doi:10.1002/ 9783527655588
2. J. Tsuji, Palladium Reagents and Catalysts: New Perspectives for the 21st Century, Wiley, Chichester, 2004. doi:10.1002/0470021209.
3. C. C. C. Johansson Seechurn, M. O. Kitching, T. J. Colacot, V. Snieckus, Angew. Chem., Int. Ed. 2012, 51, 5062
4. J.-P. Corbet, G. Mignani, Chem. Rev. 2006, 106, 2651.
5. J. Hassan,M. Sévignon,C. Gozzi,E. Schulz,M. Lemaire Chem. Rev. 2002, 102, 1359
6. C. E. I. Knappke, A. J. von Wangelin, Chem. Soc. Rev. 2011, 40, 4948
7. M. Catellani, E. Motti, N. Della Ca', R. Ferraccioli, Eur. J. Org. Chem. 2007, 4153.
8. G. Bringmann, M. Breuning, S. Tasler, Synthesis 1999, 525.
9. For reviews from our group, see: a) M. Miura, M. Nomura, in Cross-Coupling Reactions: A Practical Guide in Topics in Current Chemistry, ed. by N. Miyaura, Springer, 2002, Vol. 219, p. 211. doi:10.1007/3-540-45313-X-6
10. M. Miura, T. Satoh, in Palladium in Organic Synthesis in Topics in Organometallic Chemistry, ed. by J. Tsuji, Springer, 2005, Vol. 14, p. 55. doi:10.1007/b104129
11. T. Satoh, M. Miura, Chem. Lett. 2007, 36, 200
12. M. Miura, T. Satoh, in Modern Arylation Methods, ed. by L. Ackermann, Wiley-VCH, Weinheim, 2009, pp. 335361. doi:10.1002/9783527627325.ch10
13. T. Satoh, M. Miura, Chem.®Eur. J. 2010, 16, 11212.
14. T. Satoh, M. Miura, Synthesis 2010, 3395
15. K. Hirano, M. Miura, Synlett 2011, 294
16. K. Hirano, M. Miura, Chem. Commun. 2012, 48, 10704
17. T. Satoh, M. Miura, in Transition-Metal-Mediated Aromatic Construction, ed. by K. Tanaka, Wiley, New Jersey, 2013, pp. 683718. doi:10. 1002/9781118629871.ch25
18. K. Hirano, M.Miura, in Sustainable Catalysis: Challenges and Practices for the Pharmaceutical and Fine Chemical Industries, ed. by P. J. Dunn, K. K. (Mimi) Hii, M. J. Krische, M. T.Williams, JohnWiley & Sons, Inc., Hoboken, 2013, pp. 233267. doi:10.1002/9781118354520.ch11
19. K. Hirano, M. Miura, Top. Catal. 2014, 57, 878.
20. For selected recent reviews on transition-metal-catalyzed CH functionalization, see: a) D. A. Colby, A. S. Tsai, R. G. Bergman, J. A. Ellman, Acc. Chem. Res. 2012, 45, 814
21. K. M. Engle,T.-S. Mei,M. Wasa,J.-Q. Yu, Acc. Chem. Res. 2012, 45, 788
22. J. Yamaguchi, A. D. Yamaguchi, K. Itami, Angew. Chem., Int. Ed. 2012, 51, 8960
23. E. A.Mitchell, A. Peschiulli, N. Lefevre, L. Meerpoel, B. U. W. Maes, Chem.®Eur. J. 2012, 18, 10092.
24. S. H. Cho,J. Y. Kim,J. Kwak,S. Chang Chem. Soc. Rev. 2011 40, 5068.
25. J. Wencel-Delord, T. Dröge, F. Liu, F. Glorius, Chem. Soc. Rev. 2011, 40, 4740
26. Y. Kuninobu, K. Takai, Chem. Rev. 2011, 111, 1938
27. L. Ackermann, Chem. Rev. 2011, 111, 1315.
28. T.W. Lyons,M. S. Sanford Chem. Rev. 2010 110, 1147
29. D. A. Colby, R. G. Bergman, J. A. Ellman, Chem. Rev. 2010, 110, 624.
30. C.-L. Sun,B.-J. Li,Z.-J. Shi Chem. Commun. 2010 46, 677.
31. l) L. Ackermann, R. Vicente, A. R. Kapdi, Angew. Chem., Int. Ed. 2009, 48, 9792.
32. X. Chen, K. M. Engle, D.-H. Wang, J.-Q. Yu, Angew. Chem., Int. Ed. 2009, 48, 5094.
33. O. Daugulis, H.-Q. Do, D. Shabashov, Acc. Chem. Res. 2009, 42, 1074.
34. F. Kakiuchi, T. Kochi, Synthesis 2008, 3013.
35. Y. J. Park, J.-W. Park, C.-H. Jun, Acc. Chem. Res. 2008, 41, 222.
36. I. V. Seregin, V. Gevorgyan, Chem. Soc. Rev. 2007, 36, 1173.
37. E. M. Beccalli, G. Broggini, M. Martinelli, S. Sottocornola, Chem. Rev. 2007, 107, 5318.
38. D. Alberico, M. E. Scott, M. Lautens, Chem. Rev. 2007, 107, 174.
39. K. Godula, D. Sames, Science 2006, 312, 67.
40. For reviews on dehydrogenative coupling reactions, see: a) S. A. Girard, T. Knauber, C.-J. Li, Angew. Chem., Int. Ed. 2014, 53, 74
41. Y. Wu, J. Wang, F. Mao, F. Y. Kwong, Chem.®Asian J. 2014, 9, 26
42. J. Le Bras, J. Muzart, Chem. Rev. 2011, 111, 1170.
43. C. S. Yeung, V. M. Dong, Chem. Rev. 2011, 111, 1215
44. C. Liu, H. Zhang,W. Shi, A. Lei, Chem. Rev. 2011, 111, 1780.
45. B. Karimi, H. Behzadnia, D. Elhamifar, P. F. Akhavan, F. K. Esfahani, A. Zamani, Synthesis 2010, 1399
46. C.-J. Li, Acc. Chem. Res. 2009, 42, 335.
47. For reviews on rhodium catalysis, see: a) Ref. 4d D. A. Colby,A. S. Tsai,R. G. Bergman,J. A. Ellman Acc. Chem. Res. 2012, 45, 814
48. F. W. Patureau, J. Wencel-Delord, F. Glorius, Aldrichimica Acta 2012, 45, 31
49. G. Song, F. Wang, X. Li, Chem. Soc. Rev. 2012, 41, 3651
50. S. Chiba, Chem. Lett. 2012, 41, 1554.
51. For reviews on ruthenium catalysis, see: a) P. B. Arockiam, C. Bruneau, P. H. Dixneuf, Chem. Rev. 2012, 112, 5879
52. B. Li,P. H. Dixneuf Chem. Soc. Rev. 2013 42, 5744
53. L. Ackermann, Acc. Chem. Res. 2014, 47, 281
54. V. S. Thirunavukkarasu, S. I. Kozhushkov, L. Ackermann, Chem. Commun. 2014, 50, 29.
55. For reviews on copper catalysis, see: a) R. I. McDonald, G. Liu, S. S. Stahl, Chem. Rev. 2011, 111, 2981
56. S. E. Allen,R. R. Walvoord,R. Padilla-Salinas,M. C. Kozlowski Chem. Rev. 2013, 113,6234
57. Ref. 5. For nickel catalysis:. J. Yamaguchi, K. Muto, K. Amaike, T. Yamamoto, K. Itami, J. Synth. Org. Chem., Jpn. 2013, 71, 576
58. J. Yamaguchi, K. Muto, K. Itami, Eur. J. Org. Chem. 2013, 19
59. Y. Aihara, N. Chatani, J. Am. Chem. Soc. 2014, 136, 898. For cobalt catalysis.
60. K. Gao, N. Yoshikai, Acc. Chem. Res. 2014, 47, 1208
61. H. Ikemoto, T. Yoshino, K. Sakata, S. Matsunaga, M. Kanai, J. Am. Chem. Soc. 2014, 136, 5424.
62. For iron catalysis: i) T. Matsubara, S. Asako, L. Ilies, E. Nakamura, J. Am. Chem. Soc. 2014, 136, 646.
63. L. Cassar, J. Organomet. Chem. 1975, 93, 253
64. H. A. Dieck, R. F. Heck, J. Organomet. Chem. 1975, 93, 259
65. K. Sonogashira, Y. Tohda, N. Hagihara, Tetrahedron Lett. 1975, 16, 4467. For a recent review, see:.
66. . For a recent review, see:. T. A. Shaub, M. Kivala, in Metal-Catalyzed Cross-Coupling Reactions and More, ed. by A. de Meijere, S. Bräse, M. Oestreich, Wiley-VCH, Weinheim, 2014, pp. 665762. doi:10.1002/9783527655588.ch9.
67. T. Mizoroki, K. Mori, A. Ozaki, Bull. Chem. Soc. Jpn. 1971, 44, 581
68. R. F. Heck, J. P. Nolley, Jr., J. Org. Chem. 1972, 37, 2320. For a recent review, see:
69. . For a recent review, see: S. Bräse, A. de Meijere, in Metal-Catalyzed Cross-Coupling Reactions and More, ed. by A. de Meijere, S. Bräse, M. Oestreich, Wiley-VCH, Weinheim, 2014, pp. 533664. doi:10.1002/9783527655588.ch8.
70. T. Satoh, T. Itaya, M. Miura, M. Nomura, Chem. Lett. 1996, 823.
71. D. E. Ames, D. Bull, Tetrahedron 1982, 38, 383
72. D. E. Ames, A. Opalko, Tetrahedron 1984, 40, 1919.
73. S. J. Tremont, H. U. Rahman, J. Am. Chem. Soc. 1984, 106, 5759
74. J. S. McCallum, J. R. Gasdaska, L. S. Liebeskind, Tetrahedron Lett. 1989, 30, 4085.
75. T. Satoh, Y. Kawamura, M. Miura, M. Nomura, Angew. Chem., Int. Ed. Engl. 1997, 36, 1740
76. T. Satoh, J.-I. Inoh, Y. Kawamura, Y. Kawamura, M. Miura, M. Nomura, Bull. Chem. Soc. Jpn. 1998, 71, 2239.
77. S. Pascual, P. de Mendoza, A. A. C. Braga, F. Maseras, A. M. Echavarren, Tetrahedron 2008, 64, 6021
78. D. Lapointe, K. Fagnou, Chem. Lett. 2010, 39, 1118.
79. For rhodium-catalyzed arylation of phenols, see: a) R. B. Bedford, S. J. Coles, M. B. Hursthouse, M. E. Limmert, Angew. Chem., Int. Ed. 2003, 42, 112
80. S. Oi, S.-I. Watanabe, S. Fukita, Y. Inoue, Tetrahedron Lett. 2003, 44, 8665.
81. Y. Kawamura,T. Satoh,M. Miura,M. Nomura Chem. Lett. 1999, 961
82. Y. Kawamura, T. Satoh, M. Miura, M. Nomura, Chem. Lett. 1998, 931.
83. Y. Terao, H. Wakui, T. Satoh, M. Miura, M. Nomura, J. Am. Chem. Soc. 2001, 123, 10407
84. Y. Terao, H. Wakui, M. Nomoto, T. Satoh, M. Miura, M. Nomura, J. Org. Chem. 2003, 68, 5236.
85. T. Nishimura, S. Uemura, Synlett 2004, 201
86. T. Satoh, M. Miura, in Palladium in Organic Synthesis in Topics in Organometallic Chemistry, ed. by J. Tsuji, Springer, 2005, Vol. 14, p. 1. doi:10.1007/b104133
87. M. Murakami, M. Makino, S. Ashida, T. Matsuda, Bull. Chem. Soc. Jpn. 2006, 79, 1315.
88. M. Palucki, S. L. Buchwald J. Am. Chem. Soc. 1997, 119, 11108
89. B. C. Hamann, J. F. Hartwig, J. Am. Chem. Soc. 1997, 119, 12382.
90. T. Satoh,Y. Kametani,Y. Terao,M. Miura,M. Nomura, Tetrahedron Lett. 1999, 40, 5345
91. Y. Kametani, T. Satoh, M. Miura, M. Nomura, Tetrahedron Lett. 2000, 41, 2655.
92. R. Giri, S. Thapa, A. Kafle, Adv. Synth. Catal. 2014, 356, 1395.
93. S. Oi, S. Fukita, N. Hirata, N. Watanuki, S. Miyano, Y. Inoue, Org. Lett. 2001, 3, 2579
94. S. Oi, Y. Ogino, S. Fukita, Y. Inoue, Org. Lett. 2002, 4, 1783
95. S. Oi, R. Funayama, T. Hattori, Y. Inoue, Tetrahedron 2008, 64, 6051
96. S. Oi, H. Sasamoto, R. Funayama, Y. Inoue, Chem. Lett. 2008, 37, 994
97. S. Oi, S. Fukita, Y. Inoue, Chem. Commun. 1998, 2439.
98. F. Kakiuchi,S. Kan, K. Igi,N. Chatani,S. Murai J. Am. Chem. Soc. 2003, 125, 1698
99. F. Kakiuchi, Y. Matsuura, S. Kan, N. Chatani, J. Am. Chem. Soc. 2005, 127, 5936.
100. S. Miyamura, H. Tsurugi, T. Satoh, M. Miura, J. Organomet. Chem. 2008, 693, 2438
101. K. Ueura, T. Satoh, M. Miura, Org. Lett. 2005, 7, 2229.
102. A. Ohta, Y. Akita, T. Ohkuwa, M. Chiba, R. Fukunaga, A. Miyafuji, T. Nakata, N. Tani, Y. Aoyagi, Heterocycles 1990, 31, 1951
103. N. Nakamura, Y. Tajima, K. Sakai, Heterocycles 1982, 17, 235. See also.
104. C. Gozzi, L. Lavenot, K. Ilg, V. Penalva, M. Lemaire, Tetrahedron Lett. 1997, 38, 8867.
105. S. Pivsa-Art, T. Satoh, Y. Kawamura, M. Miura, M. Nomura, Bull. Chem. Soc. Jpn. 1998, 71, 467.
106. For recent reviews on direct arylation of heteroarenes, see: a) Ref. 3j Ref. 4q R. Rossi, F. Bellina, M. Lessi, C. Manzini, Adv. Synth. Catal. 2014, 356, 17
107. J. Roger, A. L. Gottumukkala, H. Doucet, ChemCatChem 2010, 2, 20.
108. A. Mishra,C.-Q. Ma,P. Bäuerle Chem. Rev. 2009, 109, 1141
109. K. Takimiya, S. Shinamura, I. Osaka, E. Miyazaki, Adv. Mater. 2011, 23, 4347
110. C. Wang, H. Dong, W. Hu, Y. Liu, D. Zhu, Chem. Rev. 2012, 112, 2208
111. J. Mei, Y. Diao, A. L. Appleton, L. Fang, Z. Bao, J. Am. Chem. Soc. 2013, 135, 6724.
112. A. Yokooji, T. Satoh, M. Miura, M. Nomura, Tetrahedron 2004, 60, 6757.
113. H. Watanabe, J. Kumagai, H. Tsurugi, T. Satoh, M. Miura, Chem. Lett. 2007, 36, 1336.
114. T. Okazawa, T. Satoh, M. Miura, M. Nomura J. Am. Chem. Soc. 2002, 124, 5286
115. M. Nakano, T. Satoh, M. Miura, J. Org. Chem. 2006, 71, 8309.
116. M. Nakano, H. Tsurugi, T. Satoh, M. Miura, Org. Lett. 2008, 10, 1851.
117. Q. Wang, R. Takita, Y. Kikuzaki, F. Ozawa J. Am. Chem. Soc. 2010 132, 11420
118. P. Berrouard, A. Najari, A. Pron, D. Gendron, P.-O. Morin, J.-R. Pouliot, J. Veilleux, M. Leclerc, Angew. Chem., Int. Ed. 2012, 51, 2068
119. M. Wakioka, N. Ichihara, Y. Kitano, F. Ozawa, Macromolecules 2014, 47, 626.
120. S. Ota, S. Minami, K. Hirano, T. Satoh, Y. Ie, S. Seki, Y. Aso, M. Miura RSC Adv. 2013 3, 12356
121. S. Minami, K. Hirano, T. Satoh, Y. Ie, Y. Aso, M. Miura, unpublished result.
122. Y. Ie, J. Huang, Y. Uetani, M. Karakawa, Y. Aso, Macromolecules 2012, 45, 4564.
123. A. Yokooji, T. Okazawa, T. Satoh, M. Miura, M. Nomura, Tetrahedron 2003, 59, 5685.
124. For a review on direct arylation of indole, see: L. Joucla, L. Djakovitch, Adv. Synth. Catal. 2009, 351, 673.
125. D. Takeda, M. Yamashita, K. Hirano, T. Satoh, M. Miura Chem. Lett. 2011 40, 1015
126. D. Takeda, K. Hirano, T. Satoh, M. Miura, Heterocycles 2014, 88, 275.
127. M. Miyasaka, A. Fukushima, T. Satoh, K. Hirano, M. Miura, Chem.®Eur. J. 2009, 15, 3674.
128. T. Yoshizumi, H. Tsurugi, T. Satoh, M. Miura Tetrahedron Lett. 2008, 49, 1598
129. T. Yoshizumi, T. Satoh, K. Hirano, D. Matsuo, A. Orita, J. Otera, M. Miura, Tetrahedron Lett. 2009, 50, 3273
130. T. Kawano, T. Yoshizumi, K. Hirano, T. Satoh, M. Miura, Org. Lett. 2009, 11, 3072.
131. H.-Q. Do, O. Daugulis, J. Am. Chem. Soc. 2007, 129, 12404.
132. H. Hachiya, K. Hirano, T. Satoh, M. Miura, Org. Lett. 2009, 11, 1737.
133. J. Canivet, J. Yamaguchi, I. Ban, K. Itami, Org. Lett. 2009, 11, 1733.
134. H. Hachiya, K. Hirano, T. Satoh, M. Miura, Angew. Chem., Int. Ed. 2010, 49, 2202
135. H. Hachiya, K. Hirano, T. Satoh, M. Miura, ChemCatChem 2010, 2, 1403.
136. M. Kitahara, N. Umeda, K. Hirano, T. Satoh, M. Miura, J. Am. Chem. Soc. 2011, 133, 2160.
137. M. Nishino, K. Hirano, T. Satoh, M. Miura, Angew. Chem., Int. Ed. 2012, 51, 6993.
138. V. G. Zaitsev, D. Shabashov, O. Daugulis, J. Am. Chem. Soc. 2005, 127, 13154.
139. For a review of double coordination-assisted catalytic reactions, see: G. Rouquet, N. Chatani, Angew. Chem., Int. Ed. 2013, 52, 11726.
140. M. Nishino, K. Hirano, T. Satoh, M. Miura, Angew. Chem., Int. Ed. 2013, 52, 4457.
141. R. Odani, K. Hirano, T. Satoh, M. Miura, J. Org. Chem. 2013, 78, 11045.
142. For related copper-mediated reactions, see: a) S. Fan, Z. Chen, X. Zhan, Org. Lett. 2012, 14, 4950
143. Z. Mao, Z. Wang, Z. Xu, F. Huang, Z. Yu, R. Wang Org. Lett. 2012, 14, 3854
144. X. Qin, B. Feng, J. Dong, X. Li, Y. Xue, J. Lan, J. You, J. Org. Chem. 2012, 77, 7677.
145. Y. Oda, N. Matsuyama, K. Hirano, T. Satoh, M. Miura, Synthesis 2012, 44, 1515.
146. K. Hiroya, S. Itoh, T. Sakamoto, J. Org. Chem. 2004, 69, 1126.
147. K. Okuro, M. Furuune, M. Enna, M. Miura, M. Nomura, J. Org. Chem. 1993, 58, 4716.
148. R. D. Stephens, C. E. Castro, J. Org. Chem. 1963, 28, 3313.
149. T. Kawano, N. Matsuyama, K. Hirano, T. Satoh, M. Miura, J. Org. Chem. 2010, 75, 1764.
150. A. S. Dudnik, V. Gevorgyan, Angew. Chem., Int. Ed. 2010, 49, 2096.
151. N. Matsuyama, K. Hirano, T. Satoh, M. Miura, Org. Lett. 2009, 11, 4156.
152. For related alkynylation reactions, see: a) B. P. Berciano, S. Lebrequier, F. Besseliévre, S. Piguel, Org. Lett. 2010, 12, 4038.
153. S. H. Kim, S. Chang Org. Lett. 2010, 12, 1868.
154. S. Murata, K. Teramoto, M. Miura, M. Nomura, J. Chem. Res. (S) 1993, 434
155. S. Murata, K. Teramoto, M. Miura, M. Nomura, J. Chem. Res. (M) 1993, 2827.
156. For the reaction with a peroxide as oxidant, see: Z. Li, C.-J. Li, J. Am. Chem. Soc. 2004, 126, 11810.
157. M. Kitahara, K. Hirano, H. Tsurugi, T. Satoh, M. Miura, Chem.®Eur. J. 2010, 16, 1772.
158. N. Matsuyama, M. Kitahara, K. Hirano, T. Satoh, M. Miura, Org. Lett. 2010, 12, 2358.
159. For related dehydrogenative alkynylation reactions, see: a) Y. Wei, H. Zhao, J. Kan, W. Su, M. Hong, J. Am. Chem. Soc. 2010, 132, 2522
160. S. H. Kim, J. Yoon, S. Chang Org. Lett. 2011 13, 1474.
161. I. Moritani, Y. Fujiwara Tetrahedron Lett. 1967, 8, 1119.
162. Y. Fujiwara, I. Moritani, S. Danno, R. Asano, S. Teranishi J. Am. Chem. Soc. 1969, 91, 7166
163. Y. Fujiwara, T. Jintoku, K. Takaki, CHEMTECH 1990, 636.
164. S. Murai, F. Kakiuchi, S. Sekine, Y. Tanaka, A. Kamatani, M. Sonoda, N. Chatani, Nature 1993, 366, 529.
165. M. Miura, T. Tsuda, T. Satoh, M. Nomura, Chem. Lett. 1997, 1103.
166. M. Miura, T. Tsuda, T. Satoh, S. Pivsa-Art, M. Nomura, J. Org. Chem. 1998, 63, 5211.
167. K. Ueura, T. Satoh, M. Miura Org. Lett. 2007, 9, 1407.
168. K. Ueura, T. Satoh, M. Miura J. Org. Chem. 2007, 72, 5362.
169. S. Mochida, K. Hirano, T. Satoh, M. Miura Org. Lett. 2010 12, 5776
170. S. Mochida, K. Hirano, T. Satoh, M. Miura, J. Org. Chem. 2011, 76, 3024.
171. N. Umeda, K. Hirano, T. Satoh, M. Miura, J. Org. Chem. 2009, 74, 7094.
172. Y. Unoh, Y. Hashimoto, D. Takeda, K. Hirano, T. Satoh, M. Miura, Org. Lett. 2013, 15, 3258.
173. T. Ueyama, S. Mochida, T. Fukutani, K. Hirano, T. Satoh, M. Miura, Org. Lett. 2011, 13, 706.
174. Y. Hashimoto, T. Ueyama, T. Fukutani, K. Hirano, T. Satoh, M. Miura Chem. Lett. 2011 40, 1165
175. Y. Hashimoto, T. Ortloff, K. Hirano, T. Satoh, C. Bolm, M. Miura, Chem. Lett. 2012, 41, 151.
176. Y. Unoh, K. Hirano, T. Satoh, M. Miura, Tetrahedron 2013, 69, 4454.
177. S. Mochida, N. Umeda, K. Hirano, T. Satoh, M. Miura, Chem. Lett. 2010, 39, 744.
178. For similar reactions, see: a) N. Guimond, C. Gouliaras, K. Fagnou, J. Am. Chem. Soc. 2010, 132, 6908
179. T. K. Hyster, T. Rovis J. Am. Chem. Soc. 2010 132, 10565
180. G. Song, D. Chen, C.-L. Pan, R. H. Crabtree, X. Li, J. Org. Chem. 2010, 75, 7487.
181. J. Seo, Y. Park, I. Jeon, T. Ryu, S. Park, P. H. Lee Org. Lett. 2013 15, 3358
182. D. Zhao, C. Nimphius, M. Lindale, F. Glorius, Org. Lett. 2013, 15, 4504.
183. K. Morimoto, K. Hirano, T. Satoh, M. Miura, Org. Lett. 2010, 12, 2068.
184. T. Fukutani, N. Umeda, K. Hirano, T. Satoh, M. Miura, Chem. Commun. 2009, 5141.
185. N. Umeda, H. Tsurugi, T. Satoh, M. Miura, Angew. Chem., Int. Ed. 2008, 47, 4019
186. N. Umeda, K. Hirano, T. Satoh, N. Shibata, H. Sato, M. Miura, J. Org. Chem. 2011, 76, 13.