Ru-Catalyzed C-H Arylation of Fluoroarenes with Aryl Halides

Journal of the American Chemical Society

Volumn 138, Issue 10, 2016, Pages 3596-3606

  Simonetti, Marco ^a,b   Perry, Gregory J P ^a   Cambeiro, Xacobe C ^a   Juliá Hernández, Francisco ^b   Arokianathar, Jude N ^b   Larrosa, Igor ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

^b QUEEN MARY UNIVERSITY OF LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84961262519     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.6b01615     Document Type: Article

References (115)

1. Bringmann, G.; Günther, C.; Ochse, M.; Schupp, O.; Tasler, S. Biaryls in Nature: A Multi-Facetted Class of Stereochemically, Biosynthetically, and Pharmacologically Intriguing Secondary Metabolites. In Progress in the Chemistry of Organic Natural Products; Herz, W., Falk, H., Kirby, G. W., Moore, R. E., Eds.; Springer: Vienna, Austria, 2001; Vol. 82, pp 1-249.
2. Hassan, J.; Sévignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359-1470 10.1021/cr000664r
3. Horton, D. A.; Bourne, G. T.; Smythe, M. L. Chem. Rev. 2003, 103, 893-930 10.1021/cr020033s
4. Bringmann, G.; Price Mortimer, A. J.; Keller, P. A.; Gresser, M. J.; Garner, J.; Breuning, M. Angew. Chem., Int. Ed. 2005, 44, 5384-5427 10.1002/anie.200462661
5. de Meijere, A.; Diederich, F. Metal-Catalyzed Cross-Coupling Reactions; Wiley-VCH: Weinheim, Germany, 2004.
6. Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259-281 10.1002/anie.199502591
7. Labinger, J. A.; Bercaw, J. E. Nature 2002, 417, 507-514 10.1038/417507a
8. Wencel-Delord, J.; Glorius, F. Nat. Chem. 2013, 5, 369-375 10.1038/nchem.1607
9. Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174-238 10.1021/cr0509760
10. Ackermann, L.; Vicente, R.; Kapdi, A. R. Angew. Chem., Int. Ed. 2009, 48, 9792-9826 10.1002/anie.200902996
11. Gutekunst, W. R.; Baran, P. S. Chem. Soc. Rev. 2011, 40, 1976-1991 10.1039/c0cs00182a
12. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147-1169 10.1021/cr900184e
13. Mkhalid, I. A. I.; Barnard, J. H.; Marder, T. B.; Murphy, J. M.; Hartwig, J. F. Chem. Rev. 2010, 110, 890-931 10.1021/cr900206p
14. Boorman, T. C.; Larrosa, I. Chem. Soc. Rev. 2011, 40, 1910-1925 10.1039/C0CS00098A
15. Wencel-Delord, J.; Droge, T.; Liu, F.; Glorius, F. Chem. Soc. Rev. 2011, 40, 4740-4761 10.1039/c1cs15083a
16. Arockiam, P. B.; Bruneau, C.; Dixneuf, P. H. Chem. Rev. 2012, 112, 5879-5918 10.1021/cr300153j
17. Engle, K. M.; Mei, T.-S.; Wasa, M.; Yu, J.-Q. Acc. Chem. Res. 2012, 45, 788-802 10.1021/ar200185g
18. Girard, S. A.; Knauber, T.; Li, C. J. Angew. Chem., Int. Ed. 2014, 53, 74-100 10.1002/anie.201304268
19. Kakiuchi, F.; Kochi, T.; Murai, S. Synlett 2014, 25, 2390-2414 10.1055/s-0034-1379210
20. Tani, S.; Uehara, T. N.; Yamaguchi, J.; Itami, K. Chem. Sci. 2014, 5, 123-135 10.1039/C3SC52199K
21. Zhang, X.-S.; Chen, K.; Shi, Z.-J. Chem. Sci. 2014, 5, 2146-2159 10.1039/c3sc53115e
22. Juliá-Hernández, F.; Simonetti, M.; Larrosa, I. Angew. Chem., Int. Ed. 2013, 52, 11458-11460 10.1002/anie.201306425
23. Schranck, J.; Tlili, A.; Beller, M. Angew. Chem., Int. Ed. 2014, 53, 9426-9428 10.1002/anie.201405714
24. Yu, D.-G.; de Azambuja, F.; Glorius, F. Angew. Chem., Int. Ed. 2014, 53, 7710-7712 10.1002/anie.201403894
25. Trost, B. M.; Toste, F. D.; Pinkerton, A. B. Chem. Rev. 2001, 101, 2067-2096 10.1021/cr000666b
26. De Sarkar, S.; Liu, W.; Kozhushkov, S. I.; Ackermann, L. Adv. Synth. Catal. 2014, 356, 1461-1479 10.1002/adsc.201400110
27. Palladium and Ruthenium, Monthly Average Prices between 21st July 2012 and 21st Jul 2015. Johnson Matthey Precious Metals Management Home Page. http://www.platinum.matthey.com/prices/price-charts (accessed Jul 21, 2015).
28. Lewis, L. N.; Smith, J. F. J. Am. Chem. Soc. 1986, 108, 2728-2735 10.1021/ja00270a036
29. Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature 1993, 366, 529-531 10.1038/366529a0
30. Kakiuchi, F.; Yamamoto, Y.; Chatani, N.; Murai, S. Chem. Lett. 1995, 681-682 10.1246/cl.1995.681
31. Kakiuchi, F.; Murai, S. Acc. Chem. Res. 2002, 35, 826-834 10.1021/ar960318p
32. Kakiuchi, F.; Matsumoto, M.; Sonoda, M.; Fukuyama, T.; Chatani, N.; Murai, S.; Furukawa, N.; Seki, Y. Chem. Lett. 2000, 750-751 10.1246/cl.2000.750
33. Kakiuchi, F.; Igi, K.; Matsumoto, M.; Chatani, N.; Murai, S. Chem. Lett. 2001, 422-423 10.1246/cl.2001.422
34. Kakiuchi, F.; Kan, S.; Igi, K.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 2003, 125, 1698-1699 10.1021/ja029273f
35. Kakiuchi, F.; Matsuura, Y.; Kan, S.; Chatani, N. J. Am. Chem. Soc. 2005, 127, 5936-5945 10.1021/ja043334n
36. Oi, S.; Fukita, S.; Hirata, N.; Watanuki, N.; Miyano, S.; Inoue, Y. Org. Lett. 2001, 3, 2579-2581 10.1021/ol016257z
37. Oi, S.; Ogino, Y.; Fukita, S.; Inoue, Y. Org. Lett. 2002, 4, 1783-1785 10.1021/ol025851l
38. Ackermann, L. Org. Lett. 2005, 7, 3123-3125 10.1021/ol051216e
39. Ackermann, L.; Althammer, A.; Born, R. Angew. Chem., Int. Ed. 2006, 45, 2619-2622 10.1002/anie.200504450
40. Ackermann, L.; Novák, P.; Vicente, R.; Hofmann, N. Angew. Chem., Int. Ed. 2009, 48, 6045-6048 10.1002/anie.200902458
41. Özdemir, I.; Demir, S.; Çetinkaya, B.; Gourlaouen, C.; Maseras, F.; Bruneau, C.; Dixneuf, P. H. J. Am. Chem. Soc. 2008, 130, 1156-1157 10.1021/ja710276x
42. Gorelsky, S. I.; Lapointe, D.; Fagnou, K. J. Am. Chem. Soc. 2008, 130, 10848-10849 10.1021/ja802533u
43. Lapointe, D.; Fagnou, K. Chem. Lett. 2010, 39, 1118-1126 10.1246/cl.2010.1118
44. Sandtorv, A. H. Adv. Synth. Catal. 2015, 357, 2403-2435 10.1002/adsc.201500374
45. Lafrance, M.; Rowley, C. N.; Woo, T. K.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 8754-8756 10.1021/ja062509l
46. Lu, P.; Boorman, T. C.; Slawin, A. M. Z.; Larrosa, I. J. Am. Chem. Soc. 2010, 132, 5580-5581 10.1021/ja101525w
47. Ahlsten, N.; Perry, G. J. P.; Cambeiro, X. C.; Boorman, T. C.; Larrosa, I. Catal. Sci. Technol. 2013, 3, 2892-2897 10.1039/c3cy00240c
48. Cambeiro, X. C.; Boorman, T. C.; Lu, P.; Larrosa, I. Angew. Chem., Int. Ed. 2013, 52, 1781-1784 10.1002/anie.201209007
49. Cambeiro, X. C.; Ahlsten, N.; Larrosa, I. J. Am. Chem. Soc. 2015, 137, 15636-15639 10.1021/jacs.5b10593
50. Do, H.-Q.; Daugulis, O. J. Am. Chem. Soc. 2008, 130, 1128-1129 10.1021/ja077862l
51. Do, H.-Q.; Khan, R. M. K.; Daugulis, O. J. Am. Chem. Soc. 2008, 130, 15185-15192 10.1021/ja805688p
52. Davies, D. L.; Donald, S. M. A.; Macgregor, S. A. J. Am. Chem. Soc. 2005, 127, 13754-13755 10.1021/ja052047w
53. García-Cuadrado, D.; Braga, A. A. C.; Maseras, F.; Echavarren, A. M. J. Am. Chem. Soc. 2006, 128, 1066-1067 10.1021/ja056165v
54. García-Cuadrado, D.; de Mendoza, P.; Braga, A. A. C.; Maseras, F.; Echavarren, A. M. J. Am. Chem. Soc. 2007, 129, 6880-6886 10.1021/ja071034a
55. Gorelsky, S. I. Coord. Chem. Rev. 2013, 257, 153-164 10.1016/j.ccr.2012.06.016
56. Gorelsky, S. I.; Lapointe, D.; Fagnou, K. J. Org. Chem. 2012, 77, 658-668 10.1021/jo202342q
57. Ackermann, L. Acc. Chem. Res. 2014, 47, 281-295 10.1021/ar3002798
58. Ackermann, L.; Vicente, R.; Althammer, A. Org. Lett. 2008, 10, 2299-2302 10.1021/ol800773x
59. Ackermann, L.; Vicente, R.; Potukuchi, H. K.; Pirovano, V. Org. Lett. 2010, 12, 5032-5035 10.1021/ol102187e
60. Ackermann, L. Chem. Rev. 2011, 111, 1315-1345 10.1021/cr100412j
61. Lail, M.; Arrowood, B. N.; Gunnoe, T. B. J. Am. Chem. Soc. 2003, 125, 7506-7507 10.1021/ja035076k
62. Youn, S. W.; Pastine, S. J.; Sames, D. Org. Lett. 2004, 6, 581-584 10.1021/ol036385i
63. Pittard, K. A.; Lee, J. P.; Cundari, T. R.; Gunnoe, T. B.; Petersen, J. L. Organometallics 2004, 23, 5514-5523 10.1021/om049508r
64. Cadierno, V.; Francos, J.; Gimeno, J. Chem. Commun. 2010, 46, 4175-4177 10.1039/c002804e
65. Tan, S. T.; Teo, Y. C.; Fan, W. Y. J. Organomet. Chem. 2012, 708-709, 58-64 10.1016/j.jorganchem.2012.02.017
66. Nishibayashi, Y.; Yamanashi, M.; Takagi, Y.; Hidai, M. Chem. Commun. 1997, 859-860 10.1039/a701115f
67. Fernandez, I.; Hermatschweiler, R.; Breher, F.; Pregosin, P. S.; Veiros, L. F.; Calhorda, M. J. Angew. Chem., Int. Ed. 2006, 45, 6386-6391 10.1002/anie.200600447
68. Bruneau, C.; Achard, M. Coord. Chem. Rev. 2012, 256, 525-536 10.1016/j.ccr.2011.10.018
69. Bustelo, E.; Dixneuf, P. H. Adv. Synth. Catal. 2005, 347, 393-397 10.1002/adsc.200404219
70. Fischmeister, C.; Toupet, L.; Dixneuf, P. H. New J. Chem. 2005, 29, 765-768 10.1039/b501305d
71. Thies, N.; Hrib, C. G.; Haak, E. Chem.-Eur. J. 2012, 18, 6302-6308 10.1002/chem.201200188
72. Guo, X.; Li, C.-J. Org. Lett. 2011, 13, 4977-4979 10.1021/ol202081c
73. Weissman, H.; Song, X.; Milstein, D. J. Am. Chem. Soc. 2001, 123, 337-338 10.1021/ja003361n
74. Klare, H. F.; Oestreich, M.; Ito, J.; Nishiyama, H.; Ohki, Y.; Tatsumi, K. J. Am. Chem. Soc. 2011, 133, 3312-3315 10.1021/ja111483r
75. Louillat, M.-L.; Patureau, F. W. Org. Lett. 2013, 15, 164-167 10.1021/ol303216u
76. Louillat, M. L.; Biafora, A.; Legros, F.; Patureau, F. W. Angew. Chem., Int. Ed. 2014, 53, 3505-3509 10.1002/anie.201308601
77. Liu, W.; Ackermann, L. Org. Lett. 2013, 15, 3484-3486 10.1021/ol401535k
78. Jessop, P. G.; Morris, R. H. Coord. Chem. Rev. 1992, 121, 155-284 10.1016/0010-8545(92)80067-2
79. Prechtl, M. H.; Holscher, M.; Ben-David, Y.; Theyssen, N.; Loschen, R.; Milstein, D.; Leitner, W. Angew. Chem., Int. Ed. 2007, 46, 2269-2272 10.1002/anie.200603677
80. Ferrer Flegeau, E.; Bruneau, C.; Dixneuf, P. H.; Jutand, A. J. Am. Chem. Soc. 2011, 133, 10161-10170 10.1021/ja201462n
81. Arockiam, P. B.; Fischmeister, C.; Bruneau, C.; Dixneuf, P. H. Angew. Chem., Int. Ed. 2010, 49, 6629-6632 10.1002/anie.201002870
82. 2] (Mes = mesityl) has been used previously in the direct arylation of several directing-group-containing arenes: Ackermann, L.; Pospech, J.; Potukuchi, H. K. Org. Lett. 2012, 14, 2146-2149 10.1021/ol300671y
83. Dyatkin, B. L.; Mochalina, E. P.; Knunyants, I. L. Tetrahedron 1965, 21, 2991-2995 10.1016/S0040-4020(01)96918-2
84. Lomas, J. S. J. Phys. Org. Chem. 2012, 25, 620-627 10.1002/poc.1953
85. Arroniz, C.; Denis, J. G.; Ironmonger, A.; Rassias, G.; Larrosa, I. Chem. Sci. 2014, 5, 3509-3514 10.1039/C4SC01215A
86. A recent report has shown a beneficial effect of electron-poor, fluorinated benzoates in alkyne aminoarylation reactions: Yang, F.; Ackermann, L. J. Org. Chem. 2014, 79, 12070-12082 10.1021/jo501884v
87. Zelonka, R. A.; Baird, M. C. J. Organomet. Chem. 1972, 44, 383-389 10.1016/S0022-328X(00)82927-7
88. Bennett, M. A.; Smith, A. K. J. Chem. Soc., Dalton Trans. 1974, 233-241 10.1039/dt9740000233
89. Weber, W.; Ford, P. C. Inorg. Chem. 1986, 25, 1088-1092 10.1021/ic00228a007
90. Fernandez, S.; Pfeffer, M.; Ritleng, V.; Sirlin, C. Organometallics 1999, 18, 2390-2394 Moreover, in the same report, substitution did not take place on ortho-ruthenated N,N-dimethylbenzylamine complexes, leading the authors to suggest a relevant role of the strongly donating pyridine ligand 10.1021/om9901067
91. Ackermann, L.; Born, R.; álvarez-Bercedo, P. Angew. Chem., Int. Ed. 2007, 46, 6364-6367 10.1002/anie.200701727
92. Ackermann, L.; Althammer, A.; Born, R. Synlett 2007, 2007, 2833-2836 10.1055/s-2007-990838
93. Ackermann, L.; Althammer, A.; Born, R. Tetrahedron 2008, 64, 6115-6124 10.1016/j.tet.2008.01.050
94. Ackermann, L.; Vicente, R. Org. Lett. 2009, 11, 4922-4925 10.1021/ol9020354
95. Luo, N.; Yu, Z. Chem.-Eur. J. 2010, 16, 787-791 10.1002/chem.200902612
96. Seki, M. ACS Catal. 2011, 1, 607-610 10.1021/cs200044t
97. 2-catalyzed arylation of N-pyrimidine-protected indoles with boronic acids, some catalytic activity is maintained even after full dissociation of the p-cymene ligand: Sollert, C.; Devaraj, K.; Orthaber, A.; Gates, P. J.; Pilarski, L. T. Chem.-Eur. J. 2015, 21, 5380-5386 10.1002/chem.201405931
98. Pd-catalysed direct arylation of fluoroarenes with aryltosylates has been described: Ackermann, L.; Fenner, S. Chem. Commun. 2011, 47, 430-432 10.1039/C0CC02360D
99. The sluggish reactivity of ortho-substituted haloarenes towards direct arylation has been previously exploited to favor oxidative coupling products. See Ackermann, L.; Novák, P.; Vicente, R.; Pirovano, V.; Potukuchi, H. K. Synthesis 2010, 2010, 2245-2253 No oxidative coupling was observed under our conditions. 10.1055/s-0029-1220010
100. Campeau, L.-C.; Parisien, M.; Jean, A.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 581-590 10.1021/ja055819x
101. Sun, C. L.; Li, H.; Yu, D. G.; Yu, M.; Zhou, X.; Lu, X. Y.; Huang, K.; Zheng, S. F.; Li, B. J.; Shi, Z. J. Nat. Chem. 2010, 2, 1044-1049 10.1038/nchem.862
102. Chang, J. W. W.; Chia, E. Y.; Chai, C. L. L.; Seayad, J. Org. Biomol. Chem. 2012, 10, 2289-2299 10.1039/c2ob06840k
103. Lesieur, M.; Lazreg, F.; Cazin, C. S. J. Chem. Commun. 2014, 50, 8927-8929 10.1039/C4CC03201B
104. Cho, J.-Y.; Iverson, C. N.; Smith, M. R. J. Am. Chem. Soc. 2000, 122, 12868-12869 10.1021/ja0013069
105. Cho, J.-Y.; Tse, M. K.; Holmes, D.; Maleczka, R. E.; Smith, M. R. Science 2002, 295, 305-308 10.1126/science.1067074
106. Cheng, C.; Hartwig, J. F. Science 2014, 343, 853-857 10.1126/science.1248042
107. Ackermann, L.; Diers, E.; Manvar, A. Org. Lett. 2012, 14, 1154-1157 10.1021/ol3000876
108. Ackermann, L.; Lygin, A. V. Org. Lett. 2011, 13, 3332-3335 10.1021/ol2010648
109. Diers, E.; Phani Kumar, N. Y.; Mejuch, T.; Marek, I.; Ackermann, L. Tetrahedron 2013, 69, 4445-4453 10.1016/j.tet.2013.01.006
110. Hubrich, J.; Himmler, T.; Rodefeld, L.; Ackermann, L. ACS Catal. 2015, 5, 4089-4093 10.1021/acscatal.5b00939
111. Ackermann, L.; Born, R.; Vicente, R. ChemSusChem 2009, 2, 546-549 10.1002/cssc.200900014
112. Ackermann, L.; Mulzer, M. Org. Lett. 2008, 10, 5043-5045 10.1021/ol802252m
113. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, revision d.01; Gaussian, Inc.: Wallingford, CT, 2009.
114. Legault, C. Y.; Garcia, Y.; Merlic, C. A.; Houk, K. N. J. Am. Chem. Soc. 2007, 129, 12664-12665 10.1021/ja075785o
115. Ricci, P.; Krämer, K.; Cambeiro, X. C.; Larrosa, I. J. Am. Chem. Soc. 2013, 135, 13258-13261 10.1021/ja405936s