Pd-catalyzed N-arylation of secondary acyclic amides: Catalyst development, scope, and computational study

Journal of the American Chemical Society

Volumn 131, Issue 46, 2009, Pages 16720-16734

  Hicks, Jacqueline D ^a   Hyde, Alan M ^a   Cuezva, Alberto Martinez ^a,b   Buchwald, Stephen L ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

^b UNIVERSITY OF BURGOS   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDATION; AROMATIC CARBON; AROMATIC COMPONENTS; ARYL AMIDE; COMPUTATIONAL STUDIES; ELECTRON-DEFICIENT; ELECTRONWITHDRAWING; METHOXY GROUP; N-ARYLATIONS; SECONDARY AMIDES; SYSTEMATIC VARIATION; TRIFLATES;

AROMATIC COMPOUNDS; CHLORINE COMPOUNDS; FLUORINE CONTAINING POLYMERS; LIGANDS; PALLADIUM; PHOSPHORUS; PHOSPHORUS COMPOUNDS;

AMIDES;

ACYCLIC AMIDE; AMIDE; AROMATIC COMPOUND; BENZENE DERIVATIVE; CARBON; CHLORIDE; LIGAND; NUCLEOPHILE; PALLADIUM; PHOSPHINE; PHOSPHORUS; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

AMIDATION; ARTICLE; ARYLATION; CATALYST; CHEMICAL BINDING; CONTROLLED STUDY; CROSS COUPLING REACTION; ELECTRON;

AMIDES; CATALYSIS; CHLORIDES; COMPUTER SIMULATION; LIGANDS; PALLADIUM; PHOSPHINES; SULFONAMIDES;

EID: 70450181102     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9044357     Document Type: Article

References (116)

1. For reviews, see: Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400.
2. (b) Kunz, K.; Scholz, U.; Ganzer, D. Synlett 2003, 2428.
3. (c) Ma, D.; Cai, Q. Acc. Chem. Res. 2008, 41, 1450.
4. (d) Jiang, L.; Buchwald, S. L. In Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany, 2004.
5. (e) Surry, D. S.; Buchwald, S. L. Angew. Chem., Int. Ed. 2008, 47, 6338.
6. For Cu-catalyzed reactions, see: (a) Shen, R.; Porco, J. A. Org. Lett. 2000, 2, 1333.
7. (b) Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727.
8. (c) Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421.
9. (c) Jiang, L.; Job, G. E.; Klapars, A.; Buchwald, S. L. Org. Lett. 2003, 5, 3667.
10. (e) Klapars, A.; Parris, S.; Anderson, K. W.; Buchwald, S. L. J. Am. Chem. Soc. 2004, 126, 3529.
11. (f) Pan, X.; Cai, Q.; Ma, D. Org. Lett. 2004, 6, 1809.
12. (g) Strieter, E. R.; Blackmond, D. G.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4120.
13. (h) Strieter, E. R.; Bhayana, B.; Buchwald, S. L. J. Am. Chem. Soc. 2009, 131, 78.
14. For the use of xantphos, see: (a) Yin, J.; Buchwald, S. L. Org. Lett. 2000, 2, 1101.
15. (b) Yin, J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 6043.
16. (c) Shen, Q.; Hartwig, J. F. J. Am. Chem. Soc. 2007, 129, 7734.
17. (d) Huang, J.; Chen, Y.; King, A. O.; Dilmeghani, M.; Larsen, R. D.; Faul, M. M. Org. Lett. 2008, 10, 2609.
18. (e) Manley, P. J.; Bilodeau, M. T. Org. Lett. 2004, 6, 2433.
19. (f) Audisio, D.; Messaoudi, S.; Peyrat, J.-F.; Brion, J.-D.; Alami, M. Tetrahedron Lett. 2007, 48, 6928.
20. (g) Messaoudi, S.; Audisio, D.; Brion, J.-D.; Alami, M. Tetrahedron 2007, 63, 10202.
21. (h) Artamkina, G. A.; Sergeev, A. G.; Beletskaya, I. P. Tetrahedron Lett. 2001, 42, 4381.
22. 3, see: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575.
23. For the use of xantphos, see: refs 3a,b and. (a) Wallace, D. J.; Klauber, D. J.; Chen, C.; Volante, R. P. Org. Lett. 2003, 5, 4749.
24. (b) Imbriglio, J. E.; DiRocco, D.; Raghavan, S.; Ball, R. G.; Tsou, N.; Mosley, R. T.; Tata, T. R.; Collitti, S. L. Tetrahedron Lett. 2008, 49, 4897.
25. For the use of XPhos, see: (c) Huang, X.; Anderson, K. W.; Zim, D.; Jiang, L.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 6653.
26. (d) Bhagwanth, S.; Waterson, A. G.; Adjabeng, G. M.; Hornberger, K. R. J. Org. Chem. 2009, 74, 4634.
27. For the use of other ligands, see: (e) Klapars, A.; Campos, K. R.; Chen, C.; Volant, R. P. Org. Lett. 2005, 7, 1185.
28. (f) Willis, M. C.; Brace, G. N.; Holmes, I. P. Synthesis 2005, 3229.
29. (a) Ikawa, T.; Barder, T. E.; Biscoe, M. R.; Buchwald, S. L. J. Am. Chem. Soc. 2007, 129, 13001.
30. (b) Fors, B. P.; Krattiger, P.; Strieter, E.; Buchwald, S. L. Org. Lett. 2008, 10, 3505.
31. (c) Fors, B. P.; Dooleweerdt, K.; Zeng, Q.; Buchwald, S. L. Tetrahedron 2009, 65, 6576.
32. For additional examples of amidations with aryl chlorides, see: (a) Ghosh, A.; Sieser, J. E.; Riou, M.; Cai, W.; Rivera-Ruiz, L. Org. Lett. 2003, 5, 2207.
33. (b) Shen, Q.; Shekhar, S.; Stambuli, J. P.; Hartwig, J. F. Angew. Chem., Int. Ed. 2005, 44, 1371.
34. (c) Ligthart, G. B. W. L.; Ohkawa, H.; Sijbesma, R. P.; Meijer, E. W. J. Org. Chem. 2006, 71, 375.
35. (d) Piguel, S.; Legraverend, M. J. Org. Chem. 2007, 72, 7026.
36. (e) McLaughlin, M.; Palucki, M.; Davies, I. W. Org. Lett. 2006, 8, 3311.
37. For an example of amidation with gem-dichloroolefins, see: (f) Ye, W.; Mo, J.; Zhao, T.; Xu, B. Chem. Commun. 2009, 3246.
38. For intramolecular examples, see: (a) Wolfe, J. P.; Rennels, R. A.; Buchwald, S. L. Tetrahedron 1996, 52, 7525.
39. (b) Wagaw, S.; Rennels, R. A.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 8451.
40. (c) Yang, B. H.; Buchwald, S. L. Org. Lett. 1999, 1, 35.
41. (d) Yamada, K.; Kubo, T.; Tokuyama, H.; Fukuyama, T. Synlett 2002, 231.
42. (e) Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 2003, 125, 5139.
43. (f) Poondra, R. R.; Turner, N. J. Org. Lett. 2005, 7, 863.
44. (g) Bonnaterre, F.; Bois-Choussy, M.; Zhu, J. Org. Lett. 2006, 8, 4351.
45. (h) Hoogenbrand, A.; Lange, J. H. M.; Iwema-Bakker, W. I.; Hartog, J. A. J.; Schaik, J.; Feenstra, R. W.; Terpstra, J. W. Tetrahedron Lett. 2006, 47, 4361.
46. (i) Feng, G.; Wu, J.; Dai, W. Tetrahedron Lett. 2007, 48, 401.
47. (j) Hoogenbrand, A.; Lange, J. H. M.; Hartog, J. A. J.; Henzen, R.; Terpstra, J. W. Tetrahedron Lett. 2007, 48, 4461.
48. (k) Furuta, T.; Kitamura, Y.; Hashimoto, A.; Fujii, S.; Tanaka, K.; Kan, T. Org. Lett. 2007, 9, 183.
49. (l) Kalinski, C.; Umkehrer, M.; Ross, G.; Kolb, J.; Burdack, C.; Hiller, W. Tetrahedron Lett. 2006, 47, 3423.
50. For isolated intermolecular examples, see: refs 2c, 3a, 3b, 5a and Deng, W.; Wang, Y.-F.; Zou, Y.; Liu, L.; Guo, Q.-X. Tetrahedron Lett. 2004, 45, 2311.
51. For secondary formamides, see: refs 2c, 3a, 3b, 4c, and 5a.
52. (a) Wagner, J.; Wagner, M. L.; Hening, W. A. Ann. Pharmacother. 1998, 36, 680.
53. (b) VanBever, W. F. M.; Niemegeers, C. J. E.; Janssen, P. A. J. J. Med. Chem. 1974, 17, 1047.
54. (c) Anderson, R.; Hokama, T.; Lee, S.-F.; Oey, R.; Elich, T.; Breazeale, S. Preparation of modulators of acetyl coenzyme A carboxylase as fungicides and pharmaceuticals. U.S. Patent 20080200461, 2008.
55. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Chemistry, 3rd ed.; John Wiley & Sons: New York, 1999; pp 503-564.
56. Fors, B. P.; Watson, D. A.; Biscoe, M. R.; Buchwald, S. L. J. Am. Chem. Soc. 2008, 130, 13552.
57. Sergeev, A. G.; Artamkina, G. A.; Beletskaya, I. P. Tetrahedron Lett. 2003, 44, 4719.
58. For a more complete ligand examination and condition optimization, see Supporting Information.
59. Aryl nonaflates can be easily prepared from the corresponding phenols and nonafluorobutanesulfonyl fluoride. For their preparation and use in C-N coupling, see: (a) Anderson, K. W.; Mendez-Perez, M.; Priego, J.; Buchwald, S. L. J. Org. Chem. 2003, 68, 9563.
60. (b) Tundel, R. E.; Anderson, K. W.; Buchwald, S. L. J. Org. Chem. 2006, 71, 430.
61. For the use of ArONf substrates in Heck reactions, see: (a) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009.
62. (b) Lyapkalo, I. M.; Webel, M.; Reibig, H.-U. Eur. J. Org. Chem. 2002, 3646.
63. Aryl nonaflates are generally more resistant to hydrolysis than the corresponding triflates. For an example, see: (a) Zhang, X.; Sui, Z. Tetrahedron Lett. 2003, 44, 3071.
64. Anderson, K. W.; Ikawa, T.; Tundel, R. E.; Buchwald, S. L. J. Am. Chem. Soc. 2006, 128, 10694.
65. Coordination of dba can result in diminished reactivity. See: (a) Fairlamb, I. J. S.; Kapdi, A. R.; Lee, A. F.; McGlacken, G. P.; Weissburger, F.; de Vries, A. H. M.; Vondervoort, L. S. Chem. - Eur. J. 2006, 12, 8750.
66. (b) Mace, Y.; Kapdi, A. R.; Fairlamb, I. J. S.; Jutand, A. Organometallics 2006, 25, 1795.
67. (c) Amatore, C.; Jutand, A. Coord. Chem. Rev. 1998, 178, 511.
68. For Cu-catalyzed arylations of N-aryl amides with aryl iodides and bromides: refs 2b, 2c, 2f and Freeman, H. S.; Butler, J. R.; Freedman, L. D. J. Org. Chem. 1978, 43, 4975.
69. Yin, J.; Buchwald, S. L., unpublished results.
70. For isolated examples of N-arylation with secondary carbamates, see: refs 3a, 3c, and Tasler, S.; Mies, J.; Lang, M. Adv. Synth. Catal. 2007, 349, 2286.
71. (a) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176.
72. (b) Grushin, V. V.; Alper, H. Chem. Rev. 1994, 94, 1047.
73. For Cu-catalyzed diarylations with aryl bromides and iodides, see: (a) Hisayuki, K.; Hiroyuki, M.; Koji, H. Method for Producing Aromatic Diamine Derivative. EP 1593665, 2005.
74. (b) Yabunouchi, N.; Kawamura, M. Aromatic Amine Derivative and Organic Electroluminescent Device Using the Same. WO2006073054, 2006.
75. (c) Kawamura, H.; Yabunouchi, N. Aromatic Triamine Compound and Organic Electroluminescent Device Using the Same. WO2006114921, 2006.
76. Dalton, J.; Barrett, C.; He, Y.; Hong, S.; Miller, D. D.; Mohler, M. L.; Narayanan, R.; Wu, Z. Nuclear Receptor Binding Agents. WO 2007/062230 A2, 2007.
77. Fujii, Y.; Shimada, T.; Koike, T.; Hosaka, K.; Tabei, K.; Namatame, T.; Tajima, A.; Yoneda, M.; Terano, A.; Hiraishi, H. Aliment Pharmacol. Ther. Symp. Ser. 2006, 2, 285.
78. Richens, D. T. Chem. Rev. 2005, 105, 1961.
79. For representative examples, see: (a) Ariafard, A.; Lin, Z. Organometallics 2006, 25, 4030.
80. (b) Legault, C. Y.; Garcia, Y.; Merlic, C. A.; Houk, K. N. J. Am. Chem. Soc. 2007, 129, 12664.
81. (c) Nova, A.; Ujaque, G.; Maseras, F.; Lledós, A.; Espinet, P. J. Am. Chem. Soc. 2006, 128, 14571.
82. (d) Á lvarez, R.; Faza, O. N.; López, C. S.; de Lera, A. R. Org. Lett. 2006, 8, 35.
83. (e) Braga, A. A. C.; Ujaque, G.; Maseras, F. Organometallics 2006, 25, 3647.
84. (f) Ananikov, V. P.; Musaev, D. G.; Morokuma, K. Organometallics 2005, 24, 715.
85. (g) Zuidema, E.; van Leeuwen, P. W. N. M.; Bo, C. Organometallics 2005, 24, 3703.
86. For examples that illustrate the importance of calculating the full ligand structure in Pd-catalyzed cross-coupling reactions, see: (a) Li, Z.; Fu, Y.; Guo, Q.; Liu, L. Organometallics 2008, 27, 4043.
87. (b) Barder, T. E.; Biscoe, M. R.; Buchwald, S. L. Organometallics 2007, 26, 2183.
88. For the calculated effect of ligand structure on the barrier to oxidative addition of aryl halides with LnPd(0), see ref 28a and(a) Kozuch, S.; Amatore, C.; Jutand, A.; Shaik, S. Organometallics 2005, 24, 2319.
89. For the effect on the overall cycle of a Pd-catalyzed Suzuki-Miyuara coupling, see: (b) Huang, Y.; Weng, C.; Hong, F. Chem. - Eur. J. 2008, 14, 4426.
90. For the effect on the barrier to reductive elimination of LnPd(II)ArX complexes, see: ref 28g and (c) Ananikov, V. P.; Musaev, D. G.; Morokuma, K. Eur. J. Inorg. Chem. 2007, 5390.
91. (d) Ariafard, A.; Yates, B. F. J. Organomet. Chem. 2009, 694, 2075.
92. For the effect on the overall cycle of Cu-catalyzed amide arylations, see: (e) Zhang, S.; Liu, L.; Fu, Y.; Guo, Q. Organometallics 2007, 26, 4546.
93. For computational studies on Rh/xantphos complexes and their behavior in hydroformylation reactions, see: (a) Landis, C. R.; Uddin, J. Dalton Trans. 2002, 729.
94. (b) van der Veen, L. A.; Keeven, P. H.; Schoemaker, G. C.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Lutz, M.; Spek, A. L. Organometallics 2000, 19, 872.
95. Frisch, M. J.; et al. Gaussian 03, revision D.01; Gaussian, Inc.: Wallingford, CT, 2004.
96. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299.
97. Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. J. Comput. Chem. 2003, 24, 669.
98. Boys, S. F.; Bernardi, F. Mol. Phys. 1970, 19, 553.
99. For instances where the correction of BSSE is important in theoretical studies of Pd-catalyzed processes, see: (a) Frankcombe, K. E.; Cavell, K. J.; Yates, B. F.; Knott, R. B. J. Phys. Chem. 1996, 100, 18363.
100. (b) Delbecq, F.; Lapouge, C. Organometallics 2000, 19, 2716.
101. (c) de Jong, G. T.; Sola, M.; Visscher, L.; Bickelhaupt, F. M. J. Chem. Phys. 2004, 121, 9982.
102. (a) Birkholz, M.-N.; Freixa, Z.; van Leeuwen, P. W. N. M. Chem. Soc. Rev. 2009, 38, 1099.
103. (b) Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Reek, J. N. H. Acc. Chem. Res. 2001, 34, 895.
104. For the cross coupling of activated aryl chlorides using a Pd/xantphos catalyst, see: refs 6c, d and (a) Itoh, T.; Mase, T. Org. Lett. 2004, 6, 4587.
105. (b) Patriciu, O.-I.; Finaru, A.-L.; Massip, S.; Léger, J.-M.; Jarry, C.; Guillaumet, G. Eur. J. Org. Chem. 2009, 3753.
106. Xantphos-Pd(II) complexes are often most stable as the trans isomer; see: ref 3b and (a) Zuideveld, M. A.; Swennenhuis, B. H. G.; Boele, M. D. K.; Guari, Y.; van Strijdonck, G. P. F.; Reek, J. N. H.; Kamer, P. C. J.; Goubitz, K.; Fraanje, J.; Lutz, M.; Spek, A. L.; van Leeuwen, P. W. N. M. Dalton Trans. 2002, 2308.
107. (b) Fujita, K.; Yamashita, M.; Puschmann, F.; Alvarez-Falcon, M. M.; Incarvito, C. D.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 9044.
108. Barder, T. E.; Walker, S. D.; Martinelli, J. M; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4685.
109. For experimentally determined binding energies of amines and anilines with dimeric SPhos·Pd(II)(Ar)(Cl) complexes, see: Biscoe, M. R.; Barder, T. E.; Buchwald, S. L. Angew. Chem., Int. Ed. 2007, 46, 7232.
110. (a) Deeth, R. J.; Smith, A.; Brown, J. M. J. Am. Chem. Soc. 2004, 126, 7144, references cited therein.
111. (b) Tanaka, D.; Romeril, S. P.; Myers, A. G. J. Am. Chem. Soc. 2005, 127, 10323.
112. Guari, Y.; van Strijdonck, G. P. F.; Boele, M. D. K.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Chem. - Eur. J. 2001, 7, 475.
113. Howells, R. D.; McCown, J. D. Chem. Rev. 1977, 77, 69.
114. Wadt, W. R.; Hay, J. J. Chem. Phys. 1985, 82, 284.
115. Hartwig, J. F. Inorg. Chem. 2007, 46, 1936.
116. For a computational study on the reductive elimination of aryl amines from biaryl monophosphine arylpalladium amido complexes, see: Barder, T. E.; Buchwald, S. L. J. Am. Chem. Soc. 2007, 129, 12003.