Recent advances in transition metal-catalyzed methylation reactions

Advanced Synthesis and Catalysis

Volumn 357, Issue 7, 2015, Pages 1333-1350

  Yan, Guobing ^a   Borah, Arun Jyoti ^a   Wang, Lianggui ^a   Yang, Minghua ^a  

^a LISHUI UNIVERSITY   (China)

Author keywords

cross coupling; methylation; transition metal catalysts

Indexed keywords

EID: 85027925315     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201400984     Document Type: Review

References (129)

1. P. K. Chiang, R. K. Gordon, J. Tal, G. C. Zeng, B. P. Doctor, K. Pardhasaradhi, P. P. McCann, FASEB J. 1996, 10, 471-480
2. E. J. Barreiro, A. E. Kümmerle, C. A. M. Fraga, Chem. Rev. 2011, 111, 5215-5246
3. Q. Zhang, W. A. van der Donk, W. Liu, Acc. Chem. Res. 2012, 45, 555-564
4. H. Schönherr, T. Cernak, Angew. Chem. 2013, 125, 12480-12492
5. Angew. Chem. Int. Ed. 2013, 52, 12256-12267
6. J. Chatterjee, F. Rechenmacher, H. Kessler, Angew. Chem. 2013, 125, 268-283
7. Angew. Chem. Int. Ed. 2013, 52, 254-269.
8. L. Friedman, Org. Synth. 1963, 43, 80
9. L. Friedman, D. L. Fishel, H. Shechter, J. Org. Chem. 1965, 30, 1453-1457
10. A. Potthast, T. Rosenau, C.-L. Chen, J. S. Gratzl, J. Org. Chem. 1995, 60, 4320-4321
11. Z. Diwu, C. Beachdel, D. H. Klaubert, Tetrahedron Lett. 1998, 39, 4987-4990
12. K. Shimada, T. Nanae, S. Aoyagi, Y. Takikawa, C. Kabuto, Tetrahedron Lett. 2001, 42, 6167-6169
13. N. Hirai, N. Sawatari, N. Nakamura, S. Sakaguchi, Y. Ishii, J. Org. Chem. 2003, 68, 6587-6890
14. S. Das, T. Bhowmick, T. Punnyamurthy, D. Dey, J. Nath, M. K. Chaudhuri, Tetrahedron Lett. 2003, 44, 4915-4917.
15. R. A. W. Johnstone, M. E. Rose, Tetrahedron 1979, 35, 2169-2173
16. A. R. Ahmad, L. K. Mehta, J. Parrick, Tetrahedron 1995, 51, 12899-12910
17. A. Basak, M. K. Nayak, A. K. Chakraborti, Tetrahedron Lett. 1998, 39, 4883-4886
18. W.-C. Shieh, S. Dell, O. Repič, Org. Lett. 2001, 3, 4279-4281.
19. N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483
20. C. Liu, H. Zhang, W. Shi, A. Lei, Chem. Rev. 2011, 111, 1780-1824
21. I. P. Beletskaya, V. P. Ananikov, Chem. Rev. 2011, 111, 1596-1636
22. Q. Xiao, Y. Zhang, J. Wang, Acc. Chem. Res. 2013, 46, 236-247.
23. K. Endo, T. Shibata, Synthesis 2012, 44, 1427-1452.
24. D. Ma, Q. Cai, Acc. Chem. Res. 2008, 41, 1450-1460
25. J. F. Hartwig, Acc. Chem. Res. 2008, 41, 1534-1544
26. F. Bellina, R. Rossi, Chem. Rev. 2010, 110, 1082-1146.
27. V. Farina, in: Comprehensive Organometallic Chemistry II, (Eds.:, E. W. Abel, F. G. A. Stone, G. Wilkinson, L. S. Hegedus,), Elsevier, Oxford, 1995; Vol. 12, Chapter 3.4.
28. W. Baidossi, A. Rosenfeld, B. C. Wassermann, S. Schutte, H. Schumann, J. Blum, Synthesis 1996, 1127-1130
29. J. Blum, D. Gelman, W. Baidossi, E. Shakh, A. Rosenfeld, Z. Aizenshtat, J. Org. Chem. 1997, 62, 8681-8686
30. J. Blum, O. Berlin, D. Milstein, Y. Ben-David, B. C. Wassermann, S. Schutte, H. Schumann, Synthesis 2000, 571-575
31. D. Gelman, H. Schumann, J. Blum, Tetrahedron Lett. 2000, 41, 7555-7558.
32. T. Cooper, A. Novak, L. D. Humphreys, M. D. Walker, S. Woodward, Adv. Synth. Catal. 2006, 348, 686-690.
33. B. Guillamet, F. Trécourt, G. Quéguiner, J. Org. Chem. 2002, 67, 8991-8994
34. J. Terao, A. Ikumi, H. Kuniyasu, N. Kambe, J. Am. Chem. Soc. 2003, 125, 5646-5647
35. Y. M. Kim, S. Yu, J. Am. Chem. Soc. 2003, 125, 1696-1697
36. K. Mikami, T. Miyamoto, M. Hatano, Chem. Commun. 2004, 2082-2083
37. L. Ackermann, R. Born, J. H. Spatz, D. Meyer, Angew. Chem. 2005, 117, 7382-7386
38. Angew. Chem. Int. Ed. 2005, 44, 7216-7219
39. T. Schaub, M. Backes, U. Radius, J. Am. Chem. Soc. 2006, 128, 15964-15965
40. T. J. Korn, M. A. Schade, S. Wirth, P. Knochel, Org. Lett. 2006, 8, 725-728.
41. T. Wang, B. J. Alfonso, J. A. Love, Org. Lett. 2007, 9, 5629-5631
42. T. Wang, J. A. Love, Organometallics 2008, 27, 3290-3296
43. H. L. Buckley, T. Wang, O. Tran, J. A. Love, Organometallics 2009, 28, 2356-2359
44. H. L. Buckley, A. D. Sun, J. A. Love, Organometallics 2009, 28, 6622-6624.
45. C. Bolm, J. Legros, J. L. Paih, L. Zani, Chem. Rev. 2004, 104, 6217-6254
46. B. D. Sherry, A. Fürstner, Acc. Chem. Res. 2008, 41, 1500-1511.
47. D. G. Yu, B. J. Li, Z. J. Shi, Acc. Chem. Res. 2010, 43, 1486-1495.
48. T. Agrawal, S. P. Cook, Org. Lett. 2014, 16, 5080-5083.
49. D. Srimani, G. Leitus, Y. Ben-David, D. Milstein, Angew. Chem. 2014, 126, 11272-11275
50. Angew. Chem. Int. Ed. 2014, 53, 11092-11095.
51. C. L. Sun, A. Fürstner, Angew. Chem. 2013, 125, 13309-13313
52. Angew. Chem. Int. Ed. 2013, 52, 13071-13075.
53. J. M. Herbert, Tetrahedron Lett. 2004, 45, 817-819.
54. J.-C. Shi, X. Zeng, E.-I. Negishi, Org. Lett. 2003, 5, 1825-1828
55. X. Zeng, Q. Hu, M. Qian, E.-I. Negishi, J. Am. Chem. Soc. 2003, 125, 13636-13637.
56. J. A. Marshall, D. Zou, Tetrahedron Lett. 2000, 41, 1347-1350
57. J. A. Marshall, E. A. V. Devender, J. Org. Chem. 2001, 66, 8037-8041
58. M. F. Jacobsen, J. E. Moses, R. M. Adlington, J. E. Baldwin, Org. Lett. 2005, 7, 2473-2476
59. Y. C. Jung, C. H. Yoon, E. Turos, K. S. Yoo, K. W. Jung, J. Org. Chem. 2007, 72, 10114-10122
60. J. Ramharter, J. Mulzer, Org. Lett. 2009, 11, 1151-1153
61. J.-C. Han, L.-Z. Liu, Y.-Y. Chang, G.-Z. Yue, J. Guo, L.-Y. Zhou, C.-C. Li, Z. Yang, J. Org. Chem. 2013, 78, 5492-5504.
62. P. B. Arockiam, C. Bruneau, P. H. Dixneuf, Chem. Rev. 2012, 112, 5879-5918
63. S. R. Neufeldt, M. S. Sanford, Acc. Chem. Res. 2012, 45, 936-946
64. J. F. Hartwig, Acc. Chem. Res. 2012, 45, 864-873
65. G. Song, F. Wang, X. Li, Chem. Soc. Rev. 2012, 41, 3651-3678
66. T. A. Ramirez, B. Zhao, Y. Shi, Chem. Soc. Rev. 2012, 41, 931-942
67. G. Yan, A. J. Borah, M. Yang, Adv. Synth. Catal. 2014, 356, 2375-2394.
68. S. J. Tremont, H. U. Rahman, J. Am. Chem. Soc. 1984, 106, 5759-5760
69. J. S. McCallum, J. R. Gasdaska, L. S. Liebeskind, S. J. Tremont, Tetrahedron Lett. 1989, 30, 4085-4168.
70. C. Verrier, C. Hoarau, F. Marsais, Org. Biomol. Chem. 2009, 7, 647-650
71. M. J. Jang, S. W. Youn, Bull. Korean Chem. Soc. 2011, 32, 2865-2866
72. Z. Zhao, G. Chen, Org. Lett. 2011, 13, 4850-4853.
73. X. Chen, J. Li, X. Hao, C. E. Goodhue, J.-Q. Yu, J. Am. Chem. Soc. 2006, 128, 78-79.
74. X. Chen, C. E. Goodhue, J.-Q. Yu, J. Am. Chem. Soc. 2006, 128, 12634-12635
75. R. Giri, N. Maugel, J.-J. Li, D.-H. Wang, S. P. Breazzano, L. B. Saunders, J.-Q. Yu, J. Am. Chem. Soc. 2007, 129, 3510-3511
76. H.-X. Dai, A. F. Stepan, M. S. Plummer, Y.-H. Zhang, J.-Q. Yu, J. Am. Chem. Soc. 2011, 133, 7222-7228
77. P. S. Thuy-Boun, G. Villa, D. Dang, P. Richardson, S. Su, J.-Q. Yu, J. Am. Chem. Soc. 2013, 135, 17508-17513
78. J. A. Romero-Revilla, A. García-Rubia, R. G. Arrayas, M. A. Fernandez-Ibanez, J. C. Carretero, J. Org. Chem. 2011, 76, 9525-9530
79. S. R. Neufeldt, C. K. Seigerman, M. S. Sanford, Org. Lett. 2013, 15, 2302-2305.
80. Q. Chen, L. Ilies, N. Yoshikai, E. Nakamura, Org. Lett. 2011, 13, 3232-3234.
81. Y. Zhang, J. Feng, C.-J. Li, J. Am. Chem. Soc. 2008, 130, 2900-2901.
82. B. Yao, R.-J. Song, Y. Liu, Y.-X. Xie, J.-H. Li, M.-K. Wang, R.-Y. Tang, X.-G. Zhang, C.-L. Deng, Adv. Synth. Catal. 2012, 354, 1890-1896.
83. F. Pan, Z.-Q. Lei, H. Wang, H. Li, J. Sun, Z.-J. Shi, Angew. Chem. 2013, 125, 2117-2121
84. Angew. Chem. Int. Ed. 2013, 52, 2063-2067.
85. G. Yan, X. Wu, M. Yang, Org. Biomol. Chem. 2013, 11, 5558-5578.
86. Y. Li, T. Yan, K. Junge, M. Beller, Angew. Chem. 2014, 126, 10644-10648
87. Angew. Chem. Int. Ed. 2014, 53, 10476-10480.
88. D. Wang, M. Wasa, R. Giri, J.-Q. Yu, J. Am. Chem. Soc. 2008, 130, 7190-7191.
89. D. Shabashov, O. Daugulis, J. Am. Chem. Soc. 2010, 132, 3965-3972.
90. S. Y. Zhang, G. He, W. A. Nack, Y. Zhao, Q. Li, G. Chen, J. Am. Chem. Soc. 2013, 135, 2124-2127
91. S. Y. Zhang, Q. Li, G. He, W. A. Nack, G. Chen, J. Am. Chem. Soc. 2013, 135, 12135-12141.
92. D. A. Nagib, M. E. Scott, D. W. C. MacMillan, J. Am. Chem. Soc. 2009, 131, 10875-10877
93. P. V. Pham, D. A. Nagib, D. W. C. MacMillan, Angew. Chem. 2011, 123, 6243-6246
94. Angew. Chem. Int. Ed. 2011, 50, 6119-6122.
95. Y. Li, D. Xue, W. Lu, C. Wang, Z.-T. Liu, J. Xiao, Org. Lett. 2014, 16, 66-69.
96. L. K. M. Chan, D. L. Poole, D. Shen, M. P. Healy, T. J. Donohoe, Angew. Chem. 2014, 126, 780-784
97. Angew. Chem. Int. Ed. 2014, 53, 761-765.
98. S. Guo, Q. Wang, Y. Jiang, J.-T. Yu, J. Org. Chem. 2014, 79, 11285-11289.
99. R. Chinchilla, C. Nájera, Chem. Rev. 2007, 107, 874-922.
100. Y.-Y. Liu, X.-H. Yang, X.-C. Huang, W.-T. Wei, R.-J. Song, J.-H. Li, J. Org. Chem. 2013, 78, 10421-10426.
101. N. Rodríguez, L. J. Goossen, Chem. Soc. Rev. 2011, 40, 5030-5048.
102. G. Rong, D. Liu, L. Lu, H. Yan, Y. Zheng, J. Chen, J. Mao, Tetrahedron 2014, 70, 5033-5037.
103. S. S. Brown, J. Stutz, Chem. Soc. Rev. 2012, 41, 6405-6447
104. M. D. Tzirakis, M. Orfanopoulos, Chem. Rev. 2013, 113, 5262-5321
105. F. Dénès, C. H. Schiesser, P. Renaud, Chem. Soc. Rev. 2013, 42, 7900-7942.
106. Q. Dai, J. Yu, Y. Jiang, S. Guo, H. Yang, J. Cheng, Chem. Commun. 2014, 50, 3865-3867.
107. Q. Dai, J.-T. Yu, X. Feng, Y. Jiang, H. Yang, J. Cheng, Adv. Synth. Catal. 2014, 356, 3341-3346.
108. M. F. Ali, B. M. ElAli, J. G. Speight, Handbook of Industrial Chemistry-Organic Chemicals, McGraw-Hill, New York, 2005
109. H.-J. Arpe, S. Hawkins, Industrial Organic Chemistry, Wiley-VCH, Weinheim, 1997.
110. O. Jacquet, X. Frogneux, C. Das Neves Gomes, T. Cantat, Chem. Sci. 2013, 4, 2127-2131.
111. Y. Li, X. Fang, K. Junge, M. Beller, Angew. Chem. 2013, 125, 9747-9750
112. Angew. Chem. Int. Ed. 2013, 52, 9568-9571.
113. K. Beydoun, T. vom Stein, J. Klankermayer, W. Leitner, Angew. Chem. 2013, 125, 9733-9736
114. Angew. Chem. Int. Ed. 2013, 52, 9554-9557
115. Y. Li, I. Sorribes, T. Yan, K. Junge, M. Beller, Angew. Chem. 2013, 125, 12378-12382
116. Angew. Chem. Int. Ed. 2013, 52, 12156-12160.
117. X. Cui, X. Dai, Y. Zhang, Y. Deng, F. Shi, Chem. Sci. 2014, 5, 649-655
118. X. Cui, Y. Zhang, Y. Deng, F. Shi, Chem. Commun. 2014, 50, 13521-13524.
119. K. Beydoun, G. Ghattas, K. Thenert, J. Klankermayer, W. Leitner, Angew. Chem. 2014, 126, 11190-11194
120. Angew. Chem. Int. Ed. 2014, 53, 11010-11014.
121. S. Savourey, G. Lefèvre, J.-C. Berthet, T. Cantat, Chem. Commun. 2014, 50, 14033-14036.
122. J. Zheng, C. Darcel, J.-B. Sortais, Chem. Commun. 2014, 50, 14229-14232.
123. X. Jiang, C. Wang, Y. Wei, D. Xue, Z. Liu, J. Xiao, Chem. Eur. J. 2014, 20, 58-63.
124. Q. Xia, X. Liu, Y. Zhang, C. Chen, W. Chen, Org. Lett. 2013, 15, 3326-3329.
125. Y. Zhu, H. Yan, L. Lu, D. Liu, G. Rong, J. Mao, J. Org. Chem. 2013, 78, 9898-9905.
126. E. Blondiaux, J. Pouessel, T. Cantat, Angew. Chem. 2014, 126, 12382-12386
127. Angew. Chem. Int. Ed. 2014, 53, 12186-12190
128. S. Das, F. D. Bobbink, G. Laurenczy, P. J. Dyson, Angew. Chem. 2014, 126, 13090-13093
129. Angew. Chem. Int. Ed. 2014, 53, 12876-12879.