A general and practical palladium-catalyzed direct a-arylation of amides with aryl halides

Advanced Synthesis and Catalysis

Volumn 356, Issue 1, 2014, Pages 165-178

  Zheng, Bing ^a,b   Jia, Tiezheng ^a,b   Walsh, Patrick J ^b  

^a CHINA AGRICULTURAL UNIVERSITY   (China)

^b Roy and Diana Vagelos Laboratories   (United States)

Author keywords

Amides; Aryl halides; C C bond formation; Chemoselectivity; Cross coupling; Palladium

Indexed keywords

EID: 84893946106     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201300851     Document Type: Article

References (173)

1. a) B. A. Haag, Z.-G. Zhang, J.-S. Li, P. Knochel, Angew. Chem. 2010, 122, 9703-9706;
2. Angew. Chem. Int. Ed. 2010, 49, 9513-9516;
3. b) J. C. Sheehan, K. R. Henery-Logan, J. Am. Chem. Soc. 1962, 84, 2983-2990;
4. c) Y. Kaburagi, H. Tokuyama, T. Fukuyama, J. Am. Chem. Soc. 2004, 126, 10246-10247;
5. d) M. I. Youshko, V. K. Svedas, Adv. Synth. Catal. 2002, 344, 894-898.
6. a) B. Zou, K. Long, D. Ma, Org. Lett. 2005, 7, 4237-4240;
7. b) M. L. Maddess, M. N. Tackett, H. Watanabe, P. E. Brennan, C. D. Spilling, J. S. Scott, D. P. Osborn, S. V. Ley, Angew. Chem. 2007, 119, 597-603;
8. Angew. Chem. Int. Ed. 2007, 46, 591-597;
9. c) X.-Y. Liu, Z.-Z. Fang, P.-P. Dong, X.-H. Shi, Y.-J. Teng, X.-Y. Sun, Phar-mazie 2012, 67, 804-808;
10. d) H. Tang, H.-T. Zhao, S.-M. Zhong, Z.-Y. Wang, Z.-F. Chen, H. Liang, Bioorg. Med. Chem. Lett. 2012, 22, 2257-2261.
11. a) H. Tanaka, A. Kuroda, H. Marusawa, H. Hatanaka, T. Kino, T. Goto, M. Hashimoto, T. Taga, J. Am. Chem. Soc. 1987, 109, 5031-5033;
12. b) M. Kantorova, R. Kolin-ska, S. Pazoutova, A. Honzatko, V. Havlicek, M. Flieg-er, J. Nat. Prod. 2002, 65, 1039-1040;
13. c) S.-Z. Mu, J.-S. Wang, X.-S. Yang, H.-P. He, C.-S. Li, Y.-T. Di, Y. Wang, Y. Zhang, X. Fang, L.-J. Huang, X.-J. Hao, J. Nat. Prod. 2008, 71, 564-569;
14. d) M. Kuzma, P. Sedmera, A. Jegor-ov, V. Havlicek, J. Nat. Prod. 2009, 72, 159-163;
15. e) A. M. Socha, K. L. LaPlante, D. J. Russell, D. C. Rowley, Bioorg. Med. Chem. Lett. 2009, 19, 1504-1507.
16. a) R. W. Dugger, J. A. Ragan, D. H. B. Ripin, Org. Process Res. Dev. 2005, 9, 253-258;
17. b) C. A. Busacca, D. R. Fandrick, J. J. Song, C. H. Senanayake, Adv. Synth. Catal. 2011, 353, 1825-1864;
18. c) J. Magano, J. R. Dunetz, Chem. Rev. 2011, 111, 2177-2250.
19. a) T. Hama, D. A. Culkin, J. F. Hartwig, J. Am. Chem. Soc. 2006, 128, 4976-4985;
20. b) T. Hama, X. Liu, D. A. Culkin, J. F. Hartwig, J. Am. Chem. Soc. 2003, 125, 11176-11177;
21. c) K. H. Shaughnessy, B. C. Hamann, J. F. Hartwig, J. Org. Chem. 1998, 63, 6546-6553;
22. d) E. P. Kuendig, T. M. Seidel, Y.-X. Jia, G. Bernardinelli, Angew. Chem. 2007, 119, 8636-8639;
23. Angew. Chem. Int. Ed. 2007, 46, 8484-8487;
24. e) X. Luan, R. Mariz, C. Robert, M. Gatti, S. Blumentritt, A. Linden, R. Dorta, Org. Lett. 2008, 10, 5569-5572;
25. f) X. Luan, L. Wu, E. Drinkel, R. Mariz, M. Gatti, R. Dorta, Org. Lett. 2010, 12, 1912-1915;
26. g) L. Liu, N. Ishida, S. Ashida, M. Murakami, Org. Lett. 2011, 13, 1666-1669;
27. h) P. Tolstoy, S. X. Y. Lee, C. Sparr, S. V. Ley, Org. Lett. 2012, 14, 4810-4813;
28. i) L. Wu, L. Falivene, E. Drinkel, S. Grant, A. Linden, L. Cavallo, R. Dorta, Angew. Chem. 2012, 124, 2924-2927;
29. Angew. Chem. Int. Ed. 2012, 51, 2870-2873;
30. j) M. Wasa, K. S. L. Chan, X.-G. Zhang, J. He, M. Miura, J.-Q. Yu, J. Am. Chem. Soc. 2012, 134, 18570-18572.
31. For reviews, see: a) F. Bellina, R. Rossi, Chem. Rev. 2010, 110, 1082-1146;
32. b) C. C. C. Johansson, T. J. Cola-cot, Angew. Chem. 2010, 122, 686-718;
33. Angew. Chem. Int. Ed. 2010, 49, 676-707;
34. c) D. A. Culkin, J. F. Hart-wig, Acc. Chem. Res. 2003, 36, 234-245.
35. For recent reviews, see: a) M. Tobisu, N. Chatani, Angew. Chem. 2006, 118, 1713-1715;
36. Angew. Chem. Int. Ed. 2006, 45, 1683-1684;
37. b) R. Jazzar, J. Hitce, A. Renaudat, J. Sofack-Kreutzer, O. Baudoin, Chem. Eur. J. 2010, 16, 2654-2672;
38. c) M. Wasa, K. M. Engle, J.-Q. Yu, Isr. J. Chem. 2010, 50, 605-616;
39. d) O. Baudoin, Chem. Soc. Rev. 2011, 40, 4902-4911;
40. e) R. G. Bergman, Nature 2007, 446, 391-393;
41. f) X. Chen, K. M. Engle, D.-H. Wang, J.-Q. Yu, Angew. Chem. 2009, 121, 5196-5217;
42. Angew. Chem. Int. Ed. 2009, 48, 5094-5115;
43. g) O. Daugulis, H.-Q. Do, D. Shabashov, Acc. Chem. Res. 2009, 42, 1074-1086;
44. h) T. W. Lyons, M. S. Sanford, Chem. Rev. 2010, 110, 1147-1169;
45. i) C.-L. Sun, B.-J. Li, Z.-J. Shi, Chem. Rev. 2011, 111, 1293-1314;
46. for recent reviews on general C H arylation, see: j) J.-Q. Yu, R. Giri, X. Chen, Org. Biomol. Chem. 2006, 4, 4041-4047;
47. k) F. Kakiuchi, T. Kochi, Synthesis 2008, 3013-3039;
48. l) L. Ackermann, R. Vicente, A. R. Kapdi, Angew. Chem. 2009, 121, 9976-10011;
49. Angew. Chem. Int. Ed. 2009, 48, 9792-9826;
50. m) G. P. McGlacken, L. M. Bate-man, Chem. Soc. Rev. 2009, 38, 2447-2464;
51. n) L. Ackermann, Chem. Commun. 2010, 46, 4866-4877;
52. o) C. J. Scheuermann, Chem. Asian J. 2010, 5, 436-451;
53. p) L. Ackermann, Chem. Rev. 2011, 111, 1315-1345;
54. q) J. Wencel-Delord, T. Droege, F. Liu, F Glorius, Chem. Soc. Rev. 2011, 40, 4740-4761;
55. r) C. S. Yeung, V. M. Dong, Chem. Rev. 2011, 111, 1215-1292;
56. s) J. Barluen-ga, C. Valdes, Angew. Chem. 2011, 123, 7626-7640;
57. Angew. Chem. Int. Ed. 2011, 50, 7486-7500;
58. t) P. Novak, R. Martin, Curr. Org. Chem. 2011, 15, 3233-3262;
59. u) C. C. C. Johansson Seechurn, M. O. Kitching, T. J. Colacot, V. Snieckus, Angew. Chem. 2012, 124, 5150-5174;
60. Angew. Chem. Int. Ed. 2012, 51, 5062-5085;
61. v) Z. Shao, H. Zhang, Chem. Soc. Rev. 2012, 41, 560-572;
62. w) H. C. Shen, Appl. Transition Met. Catal. Drug Discovery Dev. 2012, 25-95.
63. a) M. Palucki, S. L. Buchwald, J. Am. Chem. Soc. 1997, 119, 11108-11109;
64. b) B. C. Hamann, J. F Hartwig, J. Am. Chem. Soc. 1997,119, 12382-12383;
65. c) T. Satoh, Y. Kawamura, M. Miura, M. Nomura, Angew. Chem. 1997, 109, 1820-1822;
66. Angew. Chem. Int. Ed. Engl. 1997, 36, 1740-1742;
67. d) P. Y Yeung, K. H. Chung, F Y Kwong, Org. Lett. 2011,13, 2912-2915.
68. a) K. C. Nicolaou, J. Hao, M. V. Reddy, P. B. Rao, G. Rassias, S. A. Snyder, X. Huang, D. Y. K. Chen, W. E. Brenzovich, N Giuseppone, P. Giannakakou, A. O'Brate, J. Am. Chem. Soc. 2004, 126, 12897-12906;
69. b) C. Marti, E. M. Carreira, Eur. J. Org. Chem. 2003, 2209-2219;
70. c) B. M. Trost, M. K. Brennan, Synthesis 2009, 3003-3025;
71. d) V. J. Reddy, C.J. Douglas, Org. Lett. 2010, 12, 952-955;
72. e) Z.-Q. Qian, F. Zhou, T.-P Du, B.-L. Wang, M. Ding, X.-L. Zhao, J. Zhou, Chem. Commun. 2009, 6753-6755;
73. f) A. Beyer, J. Buendia, C. Bolm, Org. Lett. 2012, 14, 3948-3951;
74. g) D. Tomita, K. Yamatsugu, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2009, 131, 6946-6948;
75. h) Y. Kato, M. Furutachi, Z. Chen, H. Mitsunuma, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2009, 131, 9168-9169;
76. i) L. Cheng, L. Liu, D. Wang, Y.-J. Chen, Org. Lett. 2009, 11, 3874-3877;
77. j) A. M. Taylor, R. A. Altman, S. L. Buchwald, J. Am. Chem. Soc. 2009, 131, 9900-9901;
78. k) K. Jiang, J. Peng, H.-L. Cui, Y.-C. Chen, Chem. Commun. 2009, 3955-3957;
79. l) R. He, C. Ding, K. Maruoka, Angew. Chem. 2009, 121, 4629-4631;
80. Angew. Chem. Int. Ed. 2009, 48, 4559-4561;
81. m) T. Bui, S. Syed, C. F. Barbas, J. Am. Chem. Soc. 2009, 131, 8758-8759;
82. n) E. C. Linton, M. C. Kozlowski, J. Am. Chem. Soc. 2008, 130, 16162-16163;
83. o) Y Yasui, H. Kamisaki, Y Takemoto, Org. Lett. 2008, 10, 3303-3306;
84. p) Y Zhou, Y Xi, J. Zhao, X. Sheng, S. Zhang, H. Zhang, Org. Lett. 2012, 14, 3116-3119;
85. q) R. A. Altman, A. M. Hyde, X. Huang, S. L. Buchwald, J. Am. Chem. Soc. 2008, 130, 9613-9620;
86. r) M. J. Durbin, M. C. Willis, Org. Lett. 2008, 10, 1413-1415.
87. The pKa values of N,N-dialkylacetamides in DMSO are around 35.0, which are decribed in Bordwell's table (F. G. Bordwell, Acc. Chem. Res. 1988, 21, 456-463).
88. For earlier examples of zinc enolate, see: a) R. C. Poller, D. Silver, J. Organomet. Chem. 1978, 157, 247-253;
89. b) H. O. House, D. S. Crumrine, A. Y. Teranishi, H. D. Olmstead, J. Am. Chem. Soc. 1973, 95, 3310-3324;
90. c) J. Bertrand, L. Gorrichon, P. Maroni, R. Meyer, L. Viteva, Tetrahedron Lett. 1982, 23, 1901-1904.
91. a) J. Cossy, A. De Filippis, D. G. Pardo, Org. Lett. 2003, 5, 3037-3039;
92. b) J. Cossy, A. de Filippis, D. G. Pardo, Synlett 2003, 2171-2174;
93. c) A. de Filippis, D. Gomez Pardo, J. Cossy, Tetrahedron 2004, 60, 9757-9767.
94. A. de Filippis, D. G. Pardo, J. Cossy, Synthesis 2004, 2930-2933.
95. a) T. Hirano, W. Li, L. Abrams, P. J. Krusic, M. F. Otta-viani, N. J. Turro, J. Org. Chem. 2000, 65, 1319-1330;
96. b) G. Mladenova, L. Chen, C. F. Rodriquez, K. W. M. Siu, L. J. Johnston, A. C. Hopkinson, E. Lee-Ruff, J. Org. Chem. 2001, 66, 1109-1114;
97. c) M. Banerjee, S. J. Emond, S. V. Lindeman, R. Rathore, J. Org. Chem. 2007, 72, 8054-8061;
98. d) S. Wan, H. Gunaydin, K. N. Houk, P. E. Floreancig, J. Am. Chem. Soc. 2007, 129, 7915-7923;
99. e) Y. Tanaka, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2010, 132, 8862-8863;
100. f) B. Cacciutto-lo, S. Poulain-Martini, E. Dunach, Eur. J. Org. Chem. 2011, 2011, 3710-3714;
101. g) D. J. Clausen, S. Wan, P. E. Floreancig, Angew. Chem. 2011, 123, 5284-5287;
102. Angew. Chem. Int. Ed. 2011, 50, 5178-5181.
103. a) J. Zhang, C. Stanciu, B. Wang, M. M. Hussain, C.-S. Da, P. J. Carroll, S. D. Dreher, P. J. Walsh, J. Am. Chem. Soc. 2011, 133, 20552-20560;
104. b) G. I. McGrew, C. Stanciu, J. Zhang, P. J. Carroll, S. D. Dreher, P. J. Walsh, Angew. Chem. 2012, 124, 11678-11681;
105. Angew. Chem. Int. Ed. 2012, 51, 11510-11513;
106. c) G. I. McGrew, J. Temaismithi, P. J. Carroll, P. J. Walsh, Angew. Chem. 2010, 122, 5673-5676;
107. Angew. Chem. Int. Ed. 2010, 49, 5541-5544.
108. a) J. Zhang, A. Bellomo, A. D. Creamer, S. D. Dreher, P. J. Walsh, J. Am. Chem. Soc. 2012, 134, 13765-13772;
109. b) A. Bellomo, J. Zhang, N. Trongsiriwat, P. J. Walsh, Chem. Sci. 2013, 4, 849-857.
110. T. Jia, A. Bellomo, K. El Baina, S. D. Dreher, P. J. Walsh, J. Am. Chem. Soc. 2013, 135, 3740-3743.
111. a) B. Zheng, T. Jia, P. J. Walsh, Org. Lett. 2013, 15, 1690-1693;
112. b) B. Zheng, T. Jia, P. J. Walsh, Org. Lett. 2013, 15, 4190-4193.
113. a) C. M. So, C. P. Lau, F. Y. Kwong, Org. Lett. 2007, 9, 2795-2798;
114. b) H. W. Lee, F. L. Lam, C. M. So, C. P. Lau, A. S. C. Chan, F. Y. Kwong, Angew. Chem. 2009, 121, 7572-7575;
115. Angew. Chem. Int. Ed. 2009, 48, 7436-7439;
116. c) C. M. So, C. P. Lau, F. Y. Kwong, Chem. Eur. J. 2011, 17, 761-765;
117. d) S. M. Wong, C. M. So, K. H. Chung, C. P. Lau, F. Y. Kwong, Eur. J. Org. Chem. 2012, 2012, 4172-4177;
118. e) J. You, J. G. Verkade, Angew. Chem. 2003, 115, 5205-5207;
119. Angew. Chem. Int. Ed. 2003, 42, 5051-5053;
120. f) P. Y. Yeung, C. P. Tsang, F. Y. Kwong, Tetrahedron Lett. 2011, 52, 7038-7041.
121. a) D. A. Culkin, J. F. Hartwig, J. Am. Chem. Soc. 2002, 124, 9330-9331;
122. b) M. Kawatsura, J. F. Hartwig, J. Am. Chem. Soc. 1999, 121, 1473-1478;
123. c) W. Su, S. Raders, J. G. Verkade, X. Liao, J. F. Hartwig, Angew. Chem. 2006, 118, 5984-5987;
124. Angew. Chem. Int. Ed. 2006, 45, 5852-5855;
125. d) L. Wu, J. F. Hartwig, J. Am. Chem. Soc. 2005, 127, 15824-15832;
126. e) J. You, J. G. Verkade, Angew. Chem. 2003,115, 5205-5207;
127. Angew. Chem. Int. Ed. 2003, 42, 5051-5053;
128. f) J. M. Fox, X. Huang, A. Chieffi, S. L. Buchwald, J. Am. Chem. Soc. 2000, 122, 1360-1370.
129. W. A. Moradi, S. L. Buchwald, J. Am. Chem. Soc. 2001, 123, 7996-8002.
130. A. Szumna, Chem. Soc. Rev. 2010, 39, 4274-4285.
131. M. Wasa, K. S. L. Chan, X.-G Zhang, J. He, M. Miura, J.-Q. Yu, J. Am. Chem. Soc. 2012,134, 18570-18572.
132. a) S. Nahm, S. M. Weinreb, Tetrahedron Lett. 1981, 22, 3815-3818;
133. b) M. P. Sibi, Org. Prep. Proced. Int. 1993, 25, 15-40;
134. c) M. Kurosu, Y. Kishi, Tetrahedron Lett. 1998, 39, 4793-4796;
135. d) M. Badioli, R. Ballini, M. Bar-tolacci, G. Bosica, E. Torregiani, E. Marcantoni, J. Org. Chem. 2002, 67, 8938-8942;
136. e) T. Kochi, J. A. Ellman, J. Am. Chem. Soc. 2004,126, 15652-15653.
137. a) B. M. Trost, F. D. Toste, K. Greenman, J. Am. Chem. Soc. 2003, 125, 4518-4526;
138. b) B. M. Trost, A. J. Frontier, J. Am. Chem. Soc. 2000, 122, 11727-11728;
139. c) B. M. Trost, J. Xie, J. D. Sieber, J. Am. Chem. Soc. 2011,133, 20611-20622;
140. d) K. L. Billingsley, S. L. Buchwald, J. Org. Chem. 2008, 73, 5589-5591.
141. A. R. Katritzky, H.-Y He, K. Suzuki, J. Org. Chem. 2000, 65, 8210-8213.
142. The pKa value of the N,N-diethyl-2-phenylacetamide C H bond in DMSO is 26.6; F. G. Bordwell, H. E. Fried, J. Org. Chem. 1981, 46, 4327-4331.
143. J. M. Humphrey, A. R. Chamberlin, Chem. Rev. 1997, 97, 2243-2266.
144. J. S. Carey, D. Laffan, C. Thomson, M. T Williams, Org. Biomol. Chem. 2006, 4, 2337-2347.
145. a) X. Deng, A. Roessler, I. Brdar, R. Faessler, J. Wu, Z. S. Sales, N. S. Mani, J. Org. Chem. 2011, 76, 8262-8269;
146. b) S. Ramurthy, A. Costales, J. M. Jansen, B. Levine, P. A. Renhowe, C. M. Shafer, S. Subramanian, Bioorg. Med. Chem. Lett. 2012, 22, 1678-1681.
147. F. G. Bordwell, H. E. Fried, J. Org. Chem. 1991, 56, 4218-4223.
148. a) A. F. Littke, G. C. Fu, Angew. Chem. 2002, 114, 4350-4386;
149. Angew. Chem. Int. Ed. 2002, 41, 4176-4211;
150. b) R. B. Bedford, C. S. J. Cazin, D. Holder, Coord. Chem. Rev. 2004, 248, 2283-2321;
151. c) J.-P Corbet, G. Mignani, Chem. Rev. 2006,106, 2651-2710;
152. d) G. C. Fu, Acc. Chem. Res. 2008, 41, 1555-1564;
153. e) R. J. Lundgren, M. Stradiotto, Chem. Eur. J. 2012, 18, 9758-9769;
154. f) R. Rossi, F. Bellina, M. Lessi, Adv. Synth. Catal. 2012, 354, 1181-1255.
155. S. Lee, J. F. Hartwig, J. Org. Chem. 2001, 66, 3402-3415.
156. a) M. Portnoy, D. Milstein, Organometallics 1993, 12, 1665-1673;
157. b) J. R. Martinelli, T P. Clark, D. A. Watson, R. H. Munday, S. L. Buchwald, Angew. Chem. 2007, 119, 8612-8615;
158. Angew. Chem. Int. Ed. 2007, 46, 8460-8463;
159. c) W Mägerlein, A. F. Indolese, M. Beller, Angew. Chem. 2001, 113, 2940-2943;
160. Angew. Chem. Int. Ed. 2001, 40, 2856-2859.
161. a) W A. Herrmann, C. Brossmer, K. Ofele, C.-P Rei-singer, T Priermeier, M. Beller, H. Fischer, Angew. Chem. 1995, 107, 1989-1992;
162. Angew. Chem. Int. Ed. Engl. 1995, 34, 1844-1848;
163. b) A. Schnyder, A. F. Indolese, M. Studer, H.-U. Blaser, Angew. Chem. 2002,114, 3820-3823;
164. Angew. Chem. Int. Ed. 2002, 41, 3668-3671;
165. c) T Kinzel, Y Zhang, S. L. Buchwald, J. Am. Chem. Soc. 2010,132,14073-14075;
166. d) W Shu, S. L. Buchwald, Chem. Sci. 2011, 2, 2321-2325;
167. e) Y Yang, N. J. Olden-huis, S. L. Buchwald, Angew. Chem. 2013,125, 643-647;
168. Angew. Chem. Int. Ed. 2013, 52, 615-619;
169. f) M. R. Biscoe, B. P. Fors, S. L. Buchwald, J. Am. Chem. Soc. 2008,130, 6686-6687;
170. g) J. Albert, J. Granell, J. Zafrilla, M. Font-Bardia, X. Solans, J. Organomet. Chem. 2005, 690, 422-429;
171. h) J. Albert, L. D Andrea, J. Granell, J. Zafrilla, M. Font-Bardia, X. Solans, J. Organomet. Chem. 2007, 692, 4895-4902.
172. a) N. C. Bruno, M. T Tudge, S. L. Buchwald, Chem. Sci. 2013, 4, 916-920;
173. b) N. C. Bruno, M. T Tudge, S. L. Buchwald, Org. Lett. 2013,15, 2876-2879.