Stereoselective Synthesis of Methylene Oxindoles via Palladium(II)-Catalyzed Intramolecular Cross-Coupling of Carbamoyl Chlorides

Journal of the American Chemical Society

Volumn 138, Issue 43, 2016, Pages 14441-14448

  Le, Christine M ^a   Sperger, Theresa ^b   Fu, Rui ^a   Hou, Xiao ^a   Lim, Yong Hwan ^a   Schoenebeck, Franziska ^b   Lautens, Mark ^a  

^a UNIVERSITY OF TORONTO   (Canada)

^b RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CHEMICAL REACTIONS; CHLORINE COMPOUNDS; HYDROCARBONS; PALLADIUM COMPOUNDS; REGIOSELECTIVITY; STEREOCHEMISTRY;

C-C BOND FORMING; CARBAMOYL CHLORIDES; COMPUTATIONAL STUDIES; INTERNAL ALKYNES; OXIDATIVE ADDITIONS; REDUCTIVE ELIMINATION; STEREOSELECTIVE METHOD; STEREOSELECTIVE SYNTHESIS;

STEREOSELECTIVITY;

ALKYNE; CARBENE; CARBON; CHLORIDE; OXINDOLE; PALLADIUM COMPLEX; VINYL DERIVATIVE;

ARTICLE; BIOTRANSFORMATION; CARBAMOYLATION; CATALYSIS; CHEMICAL MODIFICATION; CHLOROPALLADATION; COVALENT BOND; CROSS COUPLING REACTION; ELIMINATION REACTION; MOISTURE; REGIOSELECTIVITY; SYNTHESIS;

EID: 84994246457     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.6b08925     Document Type: Article

References (111)

1. Davis, S. T.; Dickerson, S. H.; Frye, S. V.; Harris, P. A.; Hunter, R. N.; Kuyper, L. F.; Lackey, K. E.; Luzzio, M. J.; Veal, J. M.; Walker, D. H. Preparation of oxindoles as protein tyrosine kinase and protein serine/threonine kinase inhibitors. Patent WO 9915500, April 1, 1999.
2. Hauf, S.; Cole, R. W.; LaTerra, S.; Zimmer, C.; Schnapp, G.; Walter, R.; Heckel, A.; van Meel, J.; Rieder, C. L.; Peters, J.-M. J. Cell Biol. 2003, 161, 281 10.1083/jcb.200208092
3. Heckel, A.; Roth, G. J.; Kley, J.; Hoerer, S.; Uphues, I. Preparation of alkyl 5-acylindolinones as inhibitors of GSK-3. Patent WO2005087727A1, September 22, 2005.
4. Grandinetti, C. A.; Goldspiel, B. R. Pharmacotherapy 2007, 27, 1125 10.1592/phco.27.8.1125
5. Hilberg, F.; Roth, G. J.; Krssak, M.; Kautschitsch, S.; Sommergruber, W.; Tontsch-Grunt, U.; Garin-Chesa, P.; Bader, G.; Zoephel, A.; Quant, J.; Heckel, A.; Rettig, W. J. Cancer Res. 2008, 68, 4774 10.1158/0008-5472.CAN-07-6307
6. Trost, B. M.; Cramer, N.; Bernsmann, H. J. Am. Chem. Soc. 2007, 129, 3086 10.1021/ja070142u
7. Trost, B. M.; Cramer, N.; Silverman, S. M. J. Am. Chem. Soc. 2007, 129, 12396 10.1021/ja075335w
8. Lin, S.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2001, 40, 1967 10.1002/1521-3773(20010518)40:10<1967::AID-ANIE1967>3.3.CO;2-H
9. Fielding, M. R.; Grigg, R.; Urch, C. J. Chem. Commun. 2000, 2239 10.1039/b006765m
10. Gabriele, B.; Salerno, G.; Veltri, L.; Costa, M.; Massera, C. Eur. J. Org. Chem. 2001, 2001, 4607 10.1002/1099-0690(200112)2001:24<4607::AID-EJOC4607>3.0.CO;2-D
11. Teichert, A.; Jantos, K.; Harms, K.; Studer, A. Org. Lett. 2004, 6, 3477 10.1021/ol048759t
12. Cheung, W. S.; Patch, R. J.; Player, M. R. J. Org. Chem. 2005, 70, 3741 10.1021/jo050016d
13. Kamijo, S.; Sasaki, Y.; Kanazawa, C.; Schüßeler, T.; Yamamoto, Y. Angew. Chem., Int. Ed. 2005, 44, 7718 10.1002/anie.200502252
14. Shintani, R.; Yamagami, T.; Hayashi, T. Org. Lett. 2006, 8, 4799 10.1021/ol061858h
15. Miura, T.; Takahashi, Y.; Murakami, M. Org. Lett. 2007, 9, 5075 10.1021/ol7024185
16. Yang, T.-M.; Liu, G. J. Comb. Chem. 2007, 9, 86 10.1021/cc060124t
17. Pinto, A.; Neuville, L.; Zhu, J. Angew. Chem., Int. Ed. 2007, 46, 3291 10.1002/anie.200605192
18. Park, J. H.; Kim, E.; Chung, Y. K. Org. Lett. 2008, 10, 4719 10.1021/ol801978n
19. Miura, T.; Toyoshima, T.; Takahashi, Y.; Murakami, M. Org. Lett. 2009, 11, 2141 10.1021/ol900759f
20. Tang, S.; Yu, Q.-F.; Peng, P.; Li, J.-H.; Zhong, P.; Tang, R.-Y. Org. Lett. 2007, 9, 3413 10.1021/ol701450n
21. Pedras, M. S. C.; Sorensen, J. L.; Okanga, F. I.; Zaharia, I. L. Bioorg. Med. Chem. Lett. 1999, 9, 3015 10.1016/S0960-894X(99)00523-5
22. Cantagrel, G.; de Carné-Carnavalet, B.; Meyer, C.; Cossy, J. Org. Lett. 2009, 11, 4262 10.1021/ol9014877
23. Beccalli, E. M.; Marchesini, A. Tetrahedron 1994, 50, 12697 10.1016/S0040-4020(01)89402-3
24. Beccalli, E. M.; Marchesini, A. Tetrahedron 1995, 51, 2353 10.1016/0040-4020(94)01092-E
25. Sassatelli, M.; Debiton, E.; Aboab, B.; Prudhomme, M.; Moreau, P. Eur. J. Med. Chem. 2006, 41, 709 10.1016/j.ejmech.2006.03.021
26. Le, C. M.; Hou, X.; Sperger, T.; Schoenebeck, F.; Lautens, M. Angew. Chem., Int. Ed. 2015, 54, 15897 10.1002/anie.201507883
27. 0-Catalyzed Carboiodination: Early Developments and Recent Advances. In New Trends in Cross-Coupling: Theory and Application; Colacot, T. J., Ed.; RSC: Cambridge, 2015; pp 276.
28. Jiang, X.; Liu, H.; Gu, Z. Asian J. Org. Chem. 2012, 1, 16 10.1002/ajoc.201200035
29. Chen, C.; Tong, X. Org. Chem. Front. 2014, 1, 439 10.1039/c4qo00004h
30. Hartwig, J. F. Inorg. Chem. 2007, 46, 1936 10.1021/ic061926w
31. Petrone, D. A.; Ye, J.; Lautens, M. Chem. Rev. 2016, 116, 8003 10.1021/acs.chemrev.6b00089
32. Newman, S. G.; Lautens, M. J. Am. Chem. Soc. 2010, 132, 11416-11417 10.1021/ja1052335
33. Quesnel, J. S.; Arndtsen, B. A. J. Am. Chem. Soc. 2013, 135, 16841 10.1021/ja4098093
34. Shen, X.; Hyde, A. M.; Buchwald, S. L. J. Am. Chem. Soc. 2010, 132, 14076 10.1021/ja107481a
35. Roy, A. H.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 1232 10.1021/ja0034592
36. Le, C. M.; Menzies, P. J. C.; Petrone, D. A.; Lautens, M. Angew. Chem., Int. Ed. 2015, 54, 254 10.1002/anie.201409248
37. Zeni, G.; Larock, R. C. Chem. Rev. 2004, 104, 2285 10.1021/cr020085h
38. Tsuji, J. Pd(0)- and Pd(II)-Catalyzed Reactions of Alkynes and Benzynes. In Palladium Reagents and Catalysts: New Perspectives for the 21st Century; Tsuji, J., Ed.; John Wiley & Sons: West Sussex, 2005; pp 565-599.
39. Lu, X. Palladium-Catalyzed Reaction via Halopalladation of π-Compounds. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-I., Ed.; John Wiley & Sons: New York, 2002; pp 2267-2287 and references therein.
40. Ogawa, A. Palladium-Catalyzed Syn-Addition Reactions of X-Pd Bonds (X = Group 15, 16, and 17 Elements). In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-I., Ed.; John Wiley & Sons: New York, 2002; pp 2841-2849 and references therein.
41. Lu, X.; Zhu, G.; Wang, Z. Synlett 1998, 1998, 115 and references therein 10.1055/s-1998-1585
42. Ma, S.; Lu, X. J. Chem. Soc., Chem. Commun. 1990, 733 10.1039/C39900000733
43. Ma, S.; Lu, X. J. Org. Chem. 1993, 58, 1245 10.1021/jo00057a043
44. Huang, X.; Sun, A. J. Org. Chem. 2000, 65, 6561 10.1021/jo0006977
45. Huang, J.-M.; Dong, Y.; Wang, X.-X.; Luo, H.-C. Chem. Commun. 2010, 46, 1035 10.1039/b923464k
46. Chen, X.; Kong, W.; Cai, H.; Kong, L.; Zhu, G. Chem. Commun. 2011, 47, 2164 10.1039/c0cc04879h
47. Chen, D.; Cao, Y.; Yuan, Z.; Cai, H.; Zheng, R.; Kong, L.; Zhu, G. J. Org. Chem. 2011, 76, 4071 10.1021/jo102406j
48. Cai, H.; Yuan, Z.; Zhu, W.; Zhu, G. Chem. Commun. 2011, 47, 8682 10.1039/c1cc13424h
49. Lu, Z.; Kong, W.; Yuan, Z.; Zhao, X.; Zhu, G. J. Org. Chem. 2011, 76, 8524 10.1021/jo2015278
50. Peng, H.; Liu, G. Org. Lett. 2011, 13, 772 10.1021/ol103039x
51. Larock, R. C.; Doty, M. J. J. Org. Chem. 1993, 58, 4579 10.1021/jo00069a017
52. Gevorgyan, V.; Quan, L.-G.; Yamamoto, Y. Tetrahedron Lett. 1999, 40, 4089 10.1016/S0040-4039(99)00656-5
53. álvarez-Bercedo, P.; Flores-Gaspar, A.; Correa, A.; Martin, R. J. Am. Chem. Soc. 2010, 132, 466 10.1021/ja909811t
54. Solé, D.; Mariani, F.; Fernández, I. Adv. Synth. Catal. 2014, 356, 3237 10.1002/adsc.201400408
55. Zhao, L.; Lu, X. Angew. Chem., Int. Ed. 2002, 41, 4343 10.1002/1521-3773(20021115)41:22<4343::AID-ANIE4343>3.0.CO;2-5
56. Quan, L. G.; Gevorgyan, V.; Yamamoto, Y. J. Am. Chem. Soc. 1999, 121, 3545 10.1021/ja983645w
57. Solé, D.; Vallverdú, L.; Solans, X.; Font-Bardía, M.; Bonjoch, J. J. Am. Chem. Soc. 2003, 125, 1587 10.1021/ja029114w
58. Quan, L. G.; Lamrani, M.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 4827 10.1021/ja000415k
59. Tao, W.; Silverberg, L. J.; Rheingold, A. L.; Heck, R. F. Organometallics 1989, 8, 2550 10.1021/om00113a006
60. Larock, R. C.; Han, X.; Doty, M. J. Tetrahedron Lett. 1998, 39, 5713 10.1016/S0040-4039(98)01182-4
61. Solé, D.; Serrano, O. Angew. Chem., Int. Ed. 2007, 46, 7270 10.1002/anie.200702176
62. Seminal report with nitriles: Larock, R. C.; Tian, Q.; Pletnev, A. A. J. Am. Chem. Soc. 1999, 121, 3238 10.1021/ja984086w
63. Solé, D.; Serrano, O. J. Org. Chem. 2008, 73, 9372 10.1021/jo8020715
64. Kamijo, S.; Sasaki, Y.; Kanazawa, C.; Schüßeler, T.; Yamamoto, Y. Angew. Chem., Int. Ed. 2005, 44, 7718 10.1002/anie.200502252
65. Takeda, A.; Kamijo, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 5662 10.1021/ja000390p
66. Yamamoto, Y.; Nakamura, I. Top. Organomet. Chem. 2005, 14, 211 10.1007/b104136
67. Solé, D.; Fernández, I. Acc. Chem. Res. 2014, 47, 168 10.1021/ar400104j
68. II species to carbamoyl chlorides, see: Hande, S. M.; Nakajima, M.; Kamisaki, H.; Tsukano, C.; Takemoto, Y. Org. Lett. 2011, 13, 1828 10.1021/ol2003447
69. Backvall, J.-E.; Nilsson, Y. I. M.; Gatti, R. G. P. Organometallics 1995, 14, 4242 10.1021/om00009a029
70. Wang, Z.; Zhang, Z.; Lu, X. Organometallics 2000, 19, 775 10.1021/om990670h
71. Zhang, Z.; Lu, X.; Xu, Z.; Zhang, Q.; Han, X. Organometallics 2001, 20, 3724 10.1021/om0101994
72. Kaneda, K.; Uchiyama, T.; Fujiwara, Y.; Imanaka, T.; Teranishi, S. J. Org. Chem. 1979, 44, 55 10.1021/jo01315a014
73. Huang, J.; Zhou, L.; Jiang, H. Angew. Chem., Int. Ed. 2006, 45, 1945 10.1002/anie.200503970
74. Ye, S.; Gao, K.; Zhou, H.; Yang, X.; Wu, J. Chem. Commun. 2009, 5406 10.1039/b909178e
75. Liu, B.; Gao, H.; Yu, Y.; Wu, W.; Jiang, H. J. Org. Chem. 2013, 78, 10319 10.1021/jo401707j
76. Ma, S.; Wu, B.; Zhao, S. Org. Lett. 2003, 5, 4429 10.1021/ol0357245
77. Ma, S.; Wu, B.; Jiang, X.; Zhao, S. J. Org. Chem. 2005, 70, 2568 10.1021/jo0480038
78. Ma, S.; Wu, B.; Jiang, X. J. Org. Chem. 2005, 70, 2588 10.1021/jo0480996
79. Zhu, G.; Zhang, Z. J. Org. Chem. 2005, 70, 3339 10.1021/jo050090w
80. Mann, B. E.; Bailey, P. M.; Maitlis, P. M. J. Am. Chem. Soc. 1975, 97, 1275 10.1021/ja00838a070
81. Li, J.; Jiang, H.; Feng, A.; Jia, L. J. Org. Chem. 1999, 64, 5984 10.1021/jo982345u
82. Thadani, A. N.; Rawal, V. H. Org. Lett. 2002, 4, 4317 10.1021/ol0269594
83. Chen, X.; Kong, W.; Cai, H.; Kong, L.; Zhu, G. Chem. Commun. 2011, 47, 2164 10.1039/c0cc04879h
84. Conditions for Suzuki cross-coupling adapted from the following: Li, P.; Lü, B.; Fu, C.; Ma, S. Org. Biomol. Chem. 2013, 11, 98 10.1039/C2OB26365C
85. 0-mediated stereoisomerization of vinyl halides:.
86. Amatore, C.; Bensalem, S.; Ghalem, S.; Jutand, A. J. Organomet. Chem. 2004, 689, 4642 10.1016/j.jorganchem.2004.05.032
87. Krasovskiy, A.; Lipshutz, B. H. Org. Lett. 2011, 13, 3818 10.1021/ol2010165
88. Lu, G.-P.; Voigtritter, K. R.; Cai, C.; Lipshutz, B. H. Chem. Commun. 2012, 48, 8661 10.1039/c2cc33294a
89. Lu, G.-P.; Voigtritter, K. R.; Cai, C.; Lipshutz, B. H. J. Org. Chem. 2012, 77, 3700 10.1021/jo300437t
90. Fruchey, E. R.; Monks, B. M.; Patterson, A. M.; Cook, S. P. Org. Lett. 2013, 15, 4362 10.1021/ol4018694
91. Pawliczek, M.; Schneider, T. F.; Maaß, C.; Stalke, D.; Werz, D. B. Angew. Chem., Int. Ed. 2015, 54, 4119 10.1002/anie.201411210
92. Zargarian, D.; Alper, H. Organometallics 1991, 10, 2914 10.1021/om00054a070
93. Zargarian, D.; Alper, H. Organometallics 1993, 12, 712 10.1021/om00027a022
94. Also see refs 4g and 5j.
95. Zhu, G.; Lu, X. Organometallics 1995, 14, 4899 10.1021/om00010a061
96. Li, X.; Pan, J.; Song, S.; Jiao, N. Chem. Sci. 2016, 7, 5384 10.1039/C6SC01148A
97. Sehnal, P.; Taylor, R. J. K.; Fairlamb, I. J. S. Chem. Rev. 2010, 110, 824 10.1021/cr9003242
98. Muñiz, K. Angew. Chem., Int. Ed. 2009, 48, 9412 10.1002/anie.200903671
99. Kochi, T.; Urano, S.; Seki, H.; Mizushima, E.; Sato, M.; Kakiuchi, F. J. Am. Chem. Soc. 2009, 131, 2792-2793 10.1021/ja8097492
100. Powers, D. C.; Lee, E.; Ariafard, A.; Sanford, M. S.; Yates, B. F.; Canty, A. J.; Ritter, T. J. Am. Chem. Soc. 2012, 134, 12002 10.1021/ja304401u
101. Deprez, N. R.; Sanford, M. S. J. Am. Chem. Soc. 2009, 131, 11234 10.1021/ja904116k
102. Powers, D. C.; Ritter, T. Acc. Chem. Res. 2012, 45, 840 10.1021/ar2001974
103. Henry, P. M. J. Am. Chem. Soc. 1971, 93, 3547 10.1021/ja00743a053
104. Henry, P. M. Acc. Chem. Res. 1973, 6, 16 10.1021/ar50061a003
105. Yu, J.; Gaunt, M. J.; Spencer, J. B. J. Org. Chem. 2002, 67, 4627 10.1021/jo015880u
106. Calculations at the CPCM (toluene) M06L/def2-TZVP//B3LYP/6-31G(d) level of theory were conducted using Gaussian 09, revision D.01, by Frisch, M. J., et al., (see Supporting Information for full reference).
107. Sperger, T.; Sanhueza, I. A.; Kalvet, I.; Schoenebeck, F. Chem. Rev. 2015, 115, 9532 Also see ref 4g 10.1021/acs.chemrev.5b00163
108. Sperger, T.; Fisher, H. C.; Schoenebeck, F. WIREs Comput. Mol. Sci. 2016, 6, 226 10.1002/wcms.1244
109. Tsang, A. S. K.; Sanhueza, I. A.; Schoenebeck, F. Chem.-Eur. J. 2014, 20, 16432 10.1002/chem.201404725
110. Proutière, F.; Schoenebeck, F. Angew. Chem., Int. Ed. 2011, 50, 8192 10.1002/anie.201101746
111. Ahlquist, M.; Norrby, P.-O. Organometallics 2007, 26, 550 10.1021/om0604932