Practical aerobic oxidations of alcohols and amines with homogeneous copper/TEMPO and related catalyst systems

Angewandte Chemie - International Edition

Volumn 53, Issue 34, 2014, Pages 8824-8838

  Ryland, Bradford L ^a   Stahl, Shannon S ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

aerobic oxidation; alcohols; amines; copper; nitroxyl radicals

Indexed keywords

ALCOHOLS; AMINES; CATALYSTS; COPPER;

AEROBIC OXIDATIONS; AMBIENT AIR; CATALYST SYSTEM; CHEMO-SELECTIVITY; NITROXYL RADICAL; ORGANIC MOLECULES; PRACTICAL METHOD; ROOM TEMPERATURE;

OXIDATION;

ALCOHOL DERIVATIVE; AMINE; AMINE OXIDE; COPPER; TEMPO;

AIR; CATALYSIS; CHEMISTRY; OXIDATION REDUCTION REACTION;

AIR; ALCOHOLS; AMINES; CATALYSIS; COPPER; CYCLIC N-OXIDES; OXIDATION-REDUCTION;

EID: 84906069534     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201403110     Document Type: Review

References (188)

1. G. Tojo, M. Fernández, Oxidation of Alcohols to Aldehydes and Ketones (Ed.:, G. Tojo,), Springer, New York, 2010
2. G. Tojo, M. Fernández, Oxidation of Primary Alcohols to Carboxylic Acids (Ed.:, G. Tojo,), Springer, New York, 2010.
3. I. W. C. E. Arends, R. A. Sheldon, Modern Oxidation Methods (Ed.:, J.-E. Bäckvall,), Wiley-VCH, Weinheim, 2004, pp. 83-118
4. T. Mallat, A. Baiker, Chem. Rev. 2004, 104, 3037-3058
5. I. E. Markõ, P. R. Giles, M. Tsukazaki, I. Chellé-Regnaut, A. Gautier, R. Dumeunier, F. Philippart, K. Doda, J.-L. Mutonkole, S. M. Brown, C. J. Urch, Adv. Inorg. Chem. 2004, 56, 211-240
6. B.-Z. Zhan, A. Thompson, Tetrahedron 2004, 60, 2917-2935
7. M. J. Schultz, M. S. Sigman, Tetrahedron 2006, 62, 8227-8241
8. T. Matsumoto, M. Ueno, N. Wang, S. Kobayashi, Chem. Asian J. 2008, 3, 196-214
9. C. Parmeggiani, F. Cardona, Green Chem. 2012, 14, 547-564.
10. For a recent comprehensive review of copper-catalyzed aerobic oxidation reactions in organic chemistry, see:, S. E. Allen, R. R. Walvoord, R. Padilla-Salinas, M. C. Kozlowski, Chem. Rev. 2013, 113, 6234-6458.
11. C. Jallabert, C. Lapinte, H. Riviere, J. Mol. Catal. 1982, 14, 75-86
12. X. Liu, A. Qiu, D. T. Sawyer, J. Am. Chem. Soc. 1993, 115, 3239-3243
13. P. Capdevielle, D. Sparfel, J. Baranne-Lafont, N. K. Cuong, M. Maumy, J. Chem. Res. 1993, 10-11.
14. E. G. Rozantsev, V. D. Sholle, Synthesis 1971, 401-414
15. R. A. Sheldon, I. W. C. E. Arends, Adv. Synth. Catal. 2004, 346, 1051-1071
16. T. Vogler, A. Studer, Synthesis 2008, 1979-1993
17. H. Karoui, F. L. Moigne, O. Ouari, P. Tordo, Stable Radicals (Ed.:, R. G. Hicks,), Wiley, Hoboken, 2010, pp. 173-229
18. L. Tebben, A. Studer, Angew. Chem. 2011, 123, 5138-5174
19. Angew. Chem. Int. Ed. 2011, 50, 5034-5068
20. S. Wertz, A. Studer, Green Chem. 2013, 15, 3116-3134
21. Q. Cao, L. M. Dornan, L. Rogan, N. L. Hughes, M. J. Muldoon, Chem. Commun. 2014, 50, 4524-4543.
22. M. Yamaguchi, T. Takata, T. Endo, Tetrahedron Lett. 1988, 29, 5671-5672
23. M. Yamaguchi, T. Miyazawa, T. Takata, T. Endo, Pure Appl. Chem. 1990, 62, 217-222
24. A. E. J. de Nooy, A. C. Besemer, H. van Bekkum, Synthesis 1996, 1153-1174
25. J. M. Bobbitt, J. Org. Chem. 1998, 63, 9367-9374
26. N. Merbouh, J. M. Bobbitt, C. Brückner, J. Org. Chem. 2004, 69, 5116-5119.
27. P. L. Anelli, C. Biffi, F. Montanari, S. Quici, J. Org. Chem. 1987, 52, 2559-2562.
28. M. Shibuya, M. Tomizawa, I. Suzuki, Y. Iwabuchi, J. Am. Chem. Soc. 2006, 128, 8412-8413
29. M. Tomizawa, M. Shibuya, Y. Iwabuchi, Org. Lett. 2009, 11, 1829-1831
30. M. Shibuya, M. Tomizawa, Y. Sasano, Y. Iwabuchi, J. Org. Chem. 2009, 74, 4619-4622
31. M. Hayashi, M. Shibuya, Y. Iwabuchi, J. Org. Chem. 2012, 77, 3005-3009
32. M. Shibuya, R. s. Doi, T. Shibuta, S.-i. Uesugi, Y. Iwabuchi, Org. Lett. 2012, 14, 5006-5009.
33. See Ref. [12] and the following references
34. B. Graetz, S. Rychnovsky, W.-H. Leu, P. Farmer, R. Lin, Tetrahedron: Asymmetry 2005, 16, 3584-3598
35. Y. Demizu, H. Shiigi, T. Oda, Y. Matsumura, O. Onomura, Tetrahedron Lett. 2008, 49, 48-52.
36. J. M. Bobbitt, C. Brückner, N. Merbouh, Org. React. 2010, 74, 103-424.
37. R. Liu, X. Liang, C. Dong, X. Hu, J. Am. Chem. Soc. 2004, 126, 4112-4113
38. R. Liu, C. Dong, X. Liang, X. Wang, X. Hu, J. Org. Chem. 2005, 70, 729-731
39. Y. Xie, W. Mo, D. Xu, Z. Shen, N. Sun, B. Hu, X. Hu, J. Org. Chem. 2007, 72, 4288-4291
40. B. Karimi, A. Biglari, J. H. Clark, V. Budarin, Angew. Chem. 2007, 119, 7348-7351
41. Angew. Chem. Int. Ed. 2007, 46, 7210-7213
42. X. Wang, R. Liu, Y. Jin, X. Liang, Chem. Eur. J. 2008, 14, 2679-2685
43. X. He, Z. Shen, W. Mo, N. Sun, B. Hu, X. Hu, Adv. Synth. Catal. 2009, 351, 89-92
44. C.-X. Miao, L.-N. He, J.-Q. Wang, J.-L. Wang, Adv. Synth. Catal. 2009, 351, 2209-2216
45. C.-X. Miao, L.-N. He, J.-L. Wang, F. Wu, J. Org. Chem. 2010, 75, 257-260
46. Y. Kuang, H. Rokubuichi, Y. Nabae, T. Hayakawa, M.-a. Kakimoto, Adv. Synth. Catal. 2010, 352, 2635-2642
47. C. Qiu, L. Jin, Z. Huang, Z. Tang, A. Lei, Z. Shen, N. Sun, W. Mo, B. Hu, X. Hu, ChemCatChem 2012, 4, 76-80
48. A. Rahimi, A. Azarpira, H. Kim, J. Ralph, S. S. Stahl, J. Am. Chem. Soc. 2013, 135, 6415-6418
49. C. Aellig, D. Scholz, S. Conrad, I. Hermans, Green Chem. 2013, 15, 1975-1980.
50. M. Shibuya, Y. Osada, Y. Sasano, M. Tomizawa, Y. Iwabuchi, J. Am. Chem. Soc. 2011, 133, 6497-6500
51. M. B. Lauber, S. S. Stahl, ACS Catal. 2013, 3, 2612-2616.
52. A. Cecchetto, F. Fontana, F. Minisci, F. Recupero, Tetrahedron Lett. 2001, 42, 6651-6653.
53. N. Wang, R. Liu, J. Chen, X. Liang, Chem. Commun. 2005, 5322-5324
54. X. Wang, X. Liang, Chin. J. Catal. 2008, 29, 935-939
55. S. Ma, J. Liu, S. Li, B. Chen, J. Cheng, J. Kuang, Y. Liu, B. Wan, Y. Wang, J. Ye, Q. Yu, W. Yuan, S. Yu, Adv. Synth. Catal. 2011, 353, 1005-1017
56. C.-X. Miao, J.-Q. Wang, B. Yu, W.-G. Cheng, J. Sun, S. Chanfreau, L.-N. He, S.-J. Zhang, Chem. Commun. 2011, 47, 2697-2699
57. L. Wang, J. Li, Y. Lv, G. Zhao, S. Gao, Appl. Organomet. Chem. 2012, 26, 37-43.
58. Y. Jing, J. Jiang, B. Yan, S. Lu, J. Jiao, H. Xue, G. Yang, G. Zheng, Adv. Synth. Catal. 2011, 353, 1146-1152
59. Y. Guan, G. Zhou, W. Yang, Heterocycl. Commun. 2014, 20, 11-13.
60. Y. Yan, X. Tong, K. Wang, X. Bai, Catal. Commun. 2014, 43, 112-115.
61. R. Ben-Daniel, P. Alsters, R. Neumann, J. Org. Chem. 2001, 66, 8650-8653.
62. M. Fabbrini, C. Galli, P. Gentili, D. Macchitella, Tetrahedron Lett. 2001, 42, 7551-7553
63. F. dAcunzo, C. Galli, B. Masci, Eur. J. Biochem. 2002, 269, 5330-5335
64. F. dAcunzo, P. Baiocco, M. Fabbrini, C. Galli, P. Gentili, Eur. J. Org. Chem. 2002, 4195-4201
65. I. W. C. E. Arends, Y.-X. Li, R. Ausan, R. A. Sheldon, Tetrahedron 2006, 62, 6659-6665
66. S. Liebminger, M. Siebenhofer, G. Guebitz, Bioresour. Technol. 2009, 100, 4541-4545
67. S. A. Tromp, I. Matijoytė, R. A. Sheldon, I. W. C. E. Arends, G. Mul, M. T. Kreutzer, J. A. Moulijn, S. de Vries, ChemCatChem 2010, 2, 827-833
68. A. Díaz-Rodríguez, I. Lavandera, S. Kanbak-Aksu, R. A. Sheldon, V. Gotor, V. Gotor-Fernández, Adv. Synth. Catal. 2012, 354, 3405-3408.
69. G.-J. ten Brink, I. W. C. E. Arends, R. A. Sheldon, Science 2000, 287, 1636-1639
70. A. Dijksman, A. Marino-González, A. Mairata i Payeras, I. W. C. E. Arends, R. A. Sheldon, J. Am. Chem. Soc. 2001, 123, 6826-6833
71. T. Matsumoto, M. Ueno, J. Kobayashi, H. Miyamura, Y. Mori, S. Kobayashi, Adv. Synth. Catal. 2007, 349, 531-534.
72. W. Brackmann, C. Gaasbeek, Recl. Trav. Chim. Pays-Bas 1966, 85, 221-241
73. W. Brackmann, C. Gaasbeek, Recl. Trav. Chim. Pays-Bas 1966, 85, 242-256
74. W. Brackmann, C. Gaasbeek, Recl. Trav. Chim. Pays-Bas 1966, 85, 257-267.
75. M. F. Semmelhack, C. R. Schmid, D. A. Cortes, C. S. Chou, J. Am. Chem. Soc. 1984, 106, 3374-3376.
76. D. Geißlmeir, W. G. Jary, H. Falk, Monatsh. Chem. 2005, 136, 1591-1599
77. N. Jiang, A. J. Ragauskas, J. Org. Chem. 2006, 71, 7087-7090
78. S. Striegler, Tetrahedron 2006, 62, 9109-9114
79. N. Jiang, D. Vinci, C. L. Liotta, C. A. Eckert, A. J. Ragauskas, Ind. Eng. Chem. Res. 2008, 47, 627-631
80. Y. Guo, J. Zhao, J. Xu, W. Wang, F. Tian, G. Yang, M. Song, J. Nat. Gas Chem. 2007, 16, 210-212
81. J. Salinas Uber, Y. Vogels, D. van den Helder, I. Mutikainen, U. Turpeinen, W. T. Fu, O. Roubeau, P. Gamez, J. Reedijk, Eur. J. Inorg. Chem. 2007, 4197-4206
82. P. J. Figiel, M. Leskelä, T. Repo, Adv. Synth. Catal. 2007, 349, 1173-1179
83. S. Mannam, S. K. Alamsetti, G. Sekar, Adv. Synth. Catal. 2007, 349, 2253-2258
84. A. Gassama, N. Hoffmann, Adv. Synth. Catal. 2008, 350, 35-39
85. Z. Lu, J. S. Costa, O. Roubeau, I. Mutikainen, U. Turpeinen, S. J. Teat, P. Gamez, J. Reedijk, Dalton Trans. 2008, 3567-3573
86. N. Jiang, A. J. Ragauskas, ChemSusChem 2008, 1, 823-825
87. P. J. Figiel, A. Sibaouih, J. U. Ahmad, M. Nieger, M. T. Räisänen, M. Leskelä, T. Repo, Adv. Synth. Catal. 2009, 351, 2625-2632
88. J. U. Ahmad, P. J. Figiel, M. T. Räisänen, M. Leskelä, T. Repo, Appl. Catal. A 2009, 371, 17-21
89. Z. Lu, T. Ladrak, O. Roubeau, J. van der Toorn, S. J. Teat, C. Massera, P. Gamez, J. Reedijk, Dalton Trans. 2009, 3559-3570
90. P. J. Figiel, A. M. Kirillov, Y. Y. Karabach, M. N. Kopylovich, A. J. L. Pombeiro, J. Mol. Catal. A 2009, 305, 178-182
91. C. J. Gartshore, D. W. Lupton, Adv. Synth. Catal. 2010, 352, 3321-3328
92. M. M. Hossain, S.-G. Shyu, Adv. Synth. Catal. 2010, 352, 3061-3068
93. S. Striegler, N. A. Dunaway, M. G. Gichinga, L. K. Milton, Tetrahedron 2010, 66, 7927-7932
94. Q. Wang, Y. Zhang, G. Zheng, Z. Tian, G. Yang, Catal. Commun. 2011, 14, 92-95
95. M. N. Kopylovich, Y. Y. Karabach, M. F. C. G. da Silva, P. J. Figiel, J. Lasri, A. J. L. Pombeiro, Chem. Eur. J. 2012, 18, 899-914
96. I. Gamba, I. Mutikainen, E. Bouwman, J. Reedijk, S. Bonnet, Eur. J. Inorg. Chem. 2013, 115-123
97. X. Liu, Q. Xia, Y. Zhang, C. Chen, W. Chen, J. Org. Chem. 2013, 78, 8531-8536.
98. I. A. Ansari, R. Gree, Org. Lett. 2002, 4, 1507-1509
99. N. Jiang, A. J. Ragauskas, Org. Lett. 2005, 7, 3689-3692
100. L. Lin, L. Ji, Y. Wei, Catal. Commun. 2008, 9, 1379-1382
101. L. Lin, M. Juanjuan, J. Liuyan, W. Yunyang, J. Mol. Catal. A 2008, 291, 1-4
102. L. L. Liu, J. J. Ma, J. Y. Xia, L. D. Li, C. Li, X. B. Zhang, J. Y. Gong, Z. W. Tong, Catal. Commun. 2011, 12, 323-326.
103. B. Betzemeier, M. Cavazzini, S. Quici, P. Knochel, Tetrahedron Lett. 2000, 41, 4343-4346
104. G. Ragagnin, B. Betzemeier, S. Quici, P. Knochel, Tetrahedron 2002, 58, 3985-3991
105. M. Contel, C. Izuel, M. Laguna, P. R. Villuendas, P. J. Alonso, R. H. Fish, Chem. Eur. J. 2003, 9, 4168-4178
106. M. Contel, P. R. Villuendas, J. Fernandez-Gallardo, P. J. Alonso, J.-M. Vincent, R. H. Fish, Inorg. Chem. 2005, 44, 9771-9778.
107. A. Dijksman, I. W. C. E. Arends, R. A. Sheldon, Synlett 2001, 102-104
108. C. W. Y. Chung, P. H. Toy, J. Comb. Chem. 2007, 9, 115-120.
109. M. Herbert, F. Montilla, A. Galindo, Dalton Trans. 2010, 39, 900-907
110. Z. Hu, F. M. Kerton, Appl. Catal. A 2012, 413, 332-339
111. G. Zhang, X. Han, Y. Luan, Y. Wang, X. Wen, L. Xu, C. Ding, J. Gao, RSC Adv. 2013, 3, 19255-19258.
112. M. N. Kopylovich, K. T. Mahmudov, M. Haukka, P. J. Figiel, A. Mizar, J. A. L. da Silva, A. J. L. Pombeiro, Eur. J. Inorg. Chem. 2011, 4175-4181
113. A. Dhakshinamoorthy, M. Alvaro, H. Garcia, ACS Catal. 2011, 1, 48-53.
114. S. Velusamy, A. Srinivasan, T. Punniyamurthy, Tetrahedron Lett. 2006, 47, 923-926.
115. P. Gamez, I. W. C. E. Arends, J. Reedijk, R. A. Sheldon, Chem. Commun. 2003, 2414-2415
116. P. Gamez, I. W. C. E. Arends, R. A. Sheldon, J. Reedijk, Adv. Synth. Catal. 2004, 346, 805-811.
117. E. T. T. Kumpulainen, A. M. P. Koskinen, Chem. Eur. J. 2009, 15, 10901-10911.
118. J. M. Hoover, S. S. Stahl, J. Am. Chem. Soc. 2011, 133, 16901-16910
119. J. M. Hoover, J. E. Steves, S. S. Stahl, Nat. Protoc. 2012, 7, 1161-1167
120. J. M. Hoover, S. S. Stahl, Org. Synth. 2013, 90, 240-250.
121. This protocol has been adapted in an undergraduate teaching laboratory:, N. J. Hill, J. M. Hoover, S. S. Stahl, J. Chem. Educ. 2013, 90, 102-105.
122. Nonappa, U. Maitra, Eur. J. Org. Chem. 2007, 3331-3336.
123. G. Mehta, B. A. Bhat, T. H. S. Kumara, Tetrahedron Lett. 2010, 51, 4069-4072.
124. X.-H. Ho, H.-J. Oh, H.-Y. Jang, Eur. J. Org. Chem. 2012, 5655-5659.
125. D. Könning, W. Hiller, M. Chistmann, Org. Lett. 2012, 14, 5258-5261.
126. J. Brioche, G. Masson, J. Zhu, Org. Lett. 2010, 12, 1432-1435.
127. C. Li, S. Bardhan, E. A. Pace, M.-C. Liang, T. D. Gilmore, J. A. Porco, Jr., Org. Lett. 2002, 4, 3267-3270
128. C. Li, J. A. Porco, J. Org. Chem. 2005, 70, 6053-6065
129. A. S. Kleinke, C. Li, N. Rabasso, J. A. Porco, Jr., Org. Lett. 2006, 8, 2847-2850.
130. G. Mehta, K. Islam, Org. Lett. 2004, 6, 807-811
131. G. Mehta, S. C. Pan, Org. Lett. 2004, 6, 811-813
132. G. Mehta, S. Roy, Org. Lett. 2004, 6, 2389-2392
133. G. Mehta, S. C. Pan, Org. Lett. 2004, 6, 3985-3988
134. G. Mehta, S. S. Ramesh, Tetrahedron Lett. 2004, 45, 1985-1987
135. G. Mehta, K. Islam, Tetrahedron Lett. 2004, 45, 7683-7687
136. G. Mehta, S. C. Pan, Tetrahedron Lett. 2005, 46, 3045-3048
137. G. Mehta, S. Roy, Tetrahedron Lett. 2008, 49, 1458-1460
138. G. Mehta, Y. C. S. Kumar, T. B. Khan, Tetrahedron Lett. 2010, 51, 5112-5115.
139. G. H. Knaus, J. Paust, (BASF, DE). DE Patent Application 3,705,785, February 24, 1987
140. W. R. Kobertz, J. M. Essigmann, J. Am. Chem. Soc. 1996, 118, 7101-7107
141. H. Ernst, H. Klaus, (Keil&Weinkauf, USA). US Patent Application 10,094,819, March 12, 2002
142. S. Kuwahara, S. Imada, Tetrahedron Lett. 2005, 46, 547-549
143. A. Fürstner, C. Aïssa, C. Chevrier, F. Teplý, C. Nevado, M. Tremblay, Angew. Chem. 2006, 118, 5964-5969
144. Angew. Chem. Int. Ed. 2006, 45, 5832-5837.
145. M. R. Brooks, D. A. Crowl, J. Loss Prev. Process Ind. 2007, 20, 144-150.
146. J. F. Greene, J. M. Hoover, D. S. Mannel, T. W. Root, S. S. Stahl, Org. Process Res. Dev. 2013, 17, 1247-1251.
147. X. Ye, M. D. Johnson, T. Diao, M. H. Yates, S. S. Stahl, Green Chem. 2010, 12, 1180-1186.
148. J. M. Hoover, B. L. Ryland, S. S. Stahl, ACS Catal. 2013, 3, 2599-2605.
149. A. Dijksman, I. W. C. E. Arends, R. A. Sheldon, Org. Biomol. Chem. 2003, 1, 3232-3237.
150. J. W. Whittaker, Chem. Rev. 2003, 103, 2347-2364.
151. Y. Wang, J. L. DuBois, B. Hedman, K. O. Hodgson, T. D. P. Stack, Science 1998, 279, 537-540.
152. A. Caneschi, A. Grand, J. Laugier, P. Rey, R. Subra, J. Am. Chem. Soc. 1988, 110, 2307-2309
153. J. Laugier, J. M. Latour, A. Caneschi, P. Rey, Inorg. Chem. 1991, 30, 4474-4477
154. M. H. Dickman, R. J. Doedens, Inorg. Chem. 1981, 20, 2677-2681.
155. C. Michel, P. Belanzoni, P. Gamez, J. Reedijk, E. J. Baerends, Inorg. Chem. 2009, 48, 11909-11920
156. L. Cheng, J. Wang, M. Wang, Z. Wu, Dalton Trans. 2010, 39, 5377-5387
157. L. Cheng, J. Wang, M. Wang, Z. Wu, Inorg. Chem. 2010, 49, 9392-9399
158. P. Belanzoni, C. Michel, E. J. Baerends, Inorg. Chem. 2011, 50, 11896-11904.
159. J. M. Hoover, B. L. Ryland, S. S. Stahl, J. Am. Chem. Soc. 2013, 135, 2357-2367.
160. J. E. Steves, S. S. Stahl, J. Am. Chem. Soc. 2013, 135, 15742-15745.
161. Y. Sasano, S. Nagasawa, M. Yamazaki, M. Shibuya, J. Park, Y. Iwabuchi, Angew. Chem. 2014, 126, 3300-3304
162. Angew. Chem. Int. Ed. 2014, 53, 3236-3240.
163. P. Capdevielle, A. Lavigne, M. Maumy, Synthesis 1989, 453-454
164. Y. Maeda, T. Nishimura, S. Uemura, Bull. Chem. Soc. Jpn. 2003, 76, 2399-2403
165. S. M. Landge, V. Atanassova, M. Thimmaiah, B. Török, Tetrahedron Lett. 2007, 48, 5161-5164
166. A. Grirrane, A. Corma, H. Garcia, J. Catal. 2009, 264, 138-144
167. C. Zhang, N. Jiao, Angew. Chem. 2010, 122, 6310-6313
168. Angew. Chem. Int. Ed. 2010, 49, 6174-6177
169. R. D. Patil, S. Adimurthy, Adv. Synth. Catal. 2011, 353, 1695-1700.
170. Z. Hu, F. M. Kerton, Org. Biomol. Chem. 2012, 10, 1618-1624.
171. T. Sonobe, K. Oisaki, M. Kanai, Chem. Sci. 2012, 3, 3249-3255.
172. J. Kim, S. S. Stahl, ACS Catal. 2013, 3, 1652-1656.
173. B. Han, X.-L. Yang, C. Wang, Y.-W. Bai, T.-C Pan, X. Chen, W. Yu, J. Org. Chem. 2012, 77, 1136-1142.
174. For an introduction to "cross-dehydrogenative coupling", see:, C.-J. Li, Acc. Chem. Res. 2009, 42, 335-344.
175. H. Tian, X. Yu, Q. Li, J. Wang, Q. Xu, Adv. Synth. Catal. 2012, 354, 2671-2677.
176. P. Capdevielle, A. Lavigne, M. Maumy, Synthesis 1989, 451-452.
177. K. Mori, K. Yamaguchi, T. Mizugaki, K. Ebitani, K. Kaneda, Chem. Commun. 2001, 461-462
178. T. Oishi, K. Yamaguchi, N. Mizuno, Angew. Chem. 2009, 121, 6404-6406
179. Angew. Chem. Int. Ed. 2009, 48, 6286-6288
180. T. Oishi, K. Yamaguchi, N. Mizuno, Top. Catal. 2010, 53, 479-486
181. T. Ishida, H. Watanabe, T. Takei, A. Hamasaki, M. Tokunaga, M. Haruta, Appl. Catal. A 2012, 425-426, 85-90
182. A. Taketoshi, X. N. Beh, J. Kuwabara, T.-a. Koizumi, T. Kanbara, Tetrahedron Lett. 2012, 53, 3573-3576.
183. C. Tao, F. Liu, Y. Zhu, W. Liu, Z. Cao, Org. Biomol. Chem. 2013, 11, 3349-3354.
184. W. Yin, C. Wang, Y. Huang, Org. Lett. 2013, 15, 1850-1853.
185. L. M. Dornan, Q. Cao, J. C. A. Flanagan, M. J. Crawford, M. J. Cook, M. J. Muldoon, Chem. Commun. 2013, 49, 6030-6032.
186. J. C. A. Flanagan, L. M. Dornan, M. G. McLaughlin, N. G. McCreanor, M. J. Cook, M. J. Muldoon, Green Chem. 2012, 14, 1281-1283.
187. J. Yu, J. Xu, M. Lu, Appl. Organomet. Chem. 2013, 27, 606-610.
188. Z. Chen, J. Chen, M. Liu, J. Ding, W. Gao, X. Huang, H. Wu, J. Org. Chem. 2013, 78, 11342-11348.