KOtBu-mediated synthesis of dimethylisoindolin-1-ones and dimethyl-5-phenylisoindolin-1-ones: Selective C-C coupling of an unreactive tertiary sp3 C-H bond

Journal of Organic Chemistry

Volumn 79, Issue 7, 2014, Pages 2944-2954

  Kumar, Sangit ^a   Bhakuni, Bhagat Singh ^a   Yadav, Abhimanyu ^a   Kumar, Shailesh ^a   Patel, Saket ^a   Sharma, Shubham ^a  

^a INDIAN INSTITUTE OF SCIENCE EDUCATION AND RESEARCH BHOPAL   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ATOMS;

ALKYL GROUPS; ALKYL RADICALS; ATOM TRANSFER; C-C COUPLING; CARBON-CENTERED RADICALS; ISOINDOLINONE; RADICAL PATHWAY; SELECTIVE FUNCTIONALIZATION;

FREE RADICAL REACTIONS;

BENZAMIDE; CHEMICAL COMPOUND; DIMETHYL 5 PHENYLISOINDOLIN 1 ONE; DIMETHYLISOINDOLIN 1 ONE; HYDROGEN; TERTIARY ALKYL GROUP; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; ARYLATION; CHEMICAL BOND; CROSS COUPLING REACTION; ELECTRON TRANSPORT; PROTON TRANSPORT; SYNTHESIS;

EID: 84898077599     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo402776u     Document Type: Article

References (87)

1. Yanagisawa, S.; Ueda, K.; Taniguchi, T.; Itami, K. Org. Lett. 2008, 10, 4673
2. Deng, G.; Ueda, K.; Yanagisawa, S.; Itami, K.; Li, C.-J. Chem. Eur. J. 2009, 15, 333
3. 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
4. Liu, W.; Cao, H.; Zhang, H.; Zhang, H.; Chung, K. H.; He, C.; Wang, H.; Kwong, F. Y.; Lei, A. J. Am. Chem. Soc. 2010, 132, 16737
5. Shirakawa, E.; Itoh, K.-i.; Higashino, T.; Hayashi, T. J. Am. Chem. Soc. 2010, 132, 15537
6. Sun, C.-L.; Gu, Y.-F.; Wang, B.; Shi, Z.-J. Chem. Eur. J. 2011, 17, 10844
7. Sun, C.-L.; Gu, Y.-F.; Huang, W.-P.; Shi, Z.-J. Chem. Commun. 2011, 47, 9813-9815
8. Shirakawa, E.; Zhang, X.; Hayashi, T. Angew. Chem., Int. Ed. 2011, 50, 4671
9. Wu, Y.; Wong, S. M.; Mao, F.; Chan, T. L.; Kwong, F. Y. Org. Lett. 2012, 14, 5306
10. Zhang, H.; Shi, R.; Ding, A.; Lu, L.; Chen, B.; Lei, A. Angew. Chem., Int. Ed. 2012, 51, 12542
11. Chan, T. L.; Wu, Y.; Choy, P. Y.; Kwong, F. Y. Chem. Eur. J. 2013, 19, 15802
12. Bajracharya, G. B.; Daugulis, O. Org. Lett. 2008, 10, 4625
13. Roman, D. S.; Takahashi, Y.; Charette, A. B. Org. Lett. 2011, 13, 3242
14. Rueping, M.; Leiendecker, M.; Das, A.; Poisson, T.; Bui, L. Chem. Commun. 2011, 47, 10629
15. Bhakuni, B. S.; Kumar, A.; Balkrishna, S. J.; Sheikh, J. A.; Konar, S.; Kumar, S. Org. Lett. 2012, 14, 2838
16. Bhakuni, B. S.; Shrimali, K.; Kumar, A.; Kumar, S. Org. Synth. 2013, 90, 164 (Collect. Vol.)
17. De, S.; Ghosh, S.; Bhunia, S.; Sheikh, J. A.; Bisai, A. Org. Lett. 2012, 14, 4466
18. Wu, Y.; Wong, S. M.; Mao, F.; Chan, T. L.; Kwong, F. Y. Org. Lett. 2012, 14, 5306
19. Tanimoro, K.; Ueno, M.; Takeda, K.; Kirihata, M.; Tanimori, S. J. Org. Chem. 2012, 77, 7844
20. Yong, G. P.; She, W. L.; Zhang, Y. M.; Li, Y. Z. Chem. Commun. 2011, 47, 11766
21. Chen, W. C.; Hsu, Y. C.; Shih, W. C.; Lee, C. Y.; Chuang, W. H.; Tsai, Y. F.; Chen, P. P.; Ong, T. G. Chem. Commun. 2012, 48, 6702
22. Bhakuni, B. S.; Yadav, A.; Kumar, S.; Kumar, S. New J. Chem. 2013, 38, 827
23. Zhao, H.; Shien, J.; Guo, J.; Yeand, R.; Zeng, H. Chem. Commun. 2013, 49, 2323
24. Liu, W.; Tian, F.; Wang, X.; Yu, H.; Bi, Y. Chem. Commun. 2013, 49, 2983
25. Buden, M. E.; Guastavino, J. F.; Rossi, R. A. Org. Lett. 2013, 15, 1174
26. Cheng, Y.; Gu, X.; Li, P. Org. Lett. 2013, 15, 2664
27. Rossi, R. A.; Pierini, A. B.; Penenory, A. B. Chem. Rev. 2003, 103, 71
28. Studer, A.; Curran, D. P. Angew. Chem., Int. Ed. 2011, 50, 5018
29. Yanagisawa, S.; Itami, K. ChemCatChem 2011, 3, 827
30. During the preparation of our paper, Ni- or 1,10-phenanthroline-catalyzed synthesis of symmetrical isoindolinones appeared: Wertjes, W. C.; Wolfe, L. C.; Waller, P. J.; Kalyani, D. Org. Lett. 2013, 15, 5986
31. Lippmann, W. U.S. Patent 4267189, 1981
32. Chem. Abstr. 1981, 95, 61988m.
33. Ferland, J.-M.; Demerson, C. A.; Humber, L. G. Can. J. Chem. 1985, 63, 361
34. Taylor, E. C.; Zhou, P.; Jenning, L. D.; Mao, Z.; Hu, B.; Jun, J.-G. Tetrahedron Lett. 1997, 38, 521
35. Brewster, J. H.; Fusco, A. M.; Carosino, L. E.; Corman, B. G. J. Org. Chem. 1963, 28, 498
36. Heidenbluth, V. K.; Tonjes, H.; Scheffier, R. J. Prakt. Chem. 1965, 30, 204
37. Watanabe, H.; Mao, C.-L.; Barnish, I. T.; Hauser, C. R. J. Org. Chem. 1969, 34, 919
38. Ang, W. S.; Halton, B. B. Aust. J. Chem. 1971, 24, 851
39. Parham, W. E.; Jones, L. D. J. Org. Chem. 1976, 41, 1188
40. Bernhard, H. O.; Reed, J. N.; Snieckus, V. J. Org. Chem. 1977, 42, 1093
41. Milewska, M. J.; Bytner, T.; Polonski, T. Synthesis 1996, 1485
42. Couture, A.; Deniau, E.; Grandclaudon, P. Tetrahedron 1997, 53, 10313
43. Couture, A.; Deniau, E.; Ionescu, D.; Grandclaudon, P. Tetrahedron. Lett. 1998, 39, 2319
44. Mori, M.; Chiba, K.; Ban, Y. J. Org. Chem. 1978, 43, 1684
45. Wilkinson, G.; Stone, F. G. A.; Abel, E. W. Comprehensive Organometallic Chemistry, 1 st ed.; Pergamon: Oxford, U.K., 1982; Vol. 1.
46. Larock, R. C.; Liu, C.-L.; Lau, H. H.; Varaprath, S. Tetrahedron Lett. 1984, 25, 4459
47. Kondo, Y.; Shiga, F.; Murata, N.; Sakamoto, T.; Yamanaka, H. Tetrahedron 1994, 50, 11803
48. Koseki, Y.; Kusano, S.; Sakata, H.; Nagasaka, T. Tetrahedron Lett. 1999, 40, 2169
49. Kundu, N. G.; Khan, M. W.; Mukhopadhyay, R. Tetrahedron 1999, 55, 12361
50. Kundu, N. G.; Khan, M. W. Tetrahedron 2000, 56, 4777
51. Lu, C.; Dubrovisky, A. V.; Larock, R. C. J. Org. Chem. 2012, 77, 8648
52. Beak, P.; Kerrick, S. T.; Gallagher, D. J. J. Am. Chem. Soc. 1993, 115, 10628
53. Beckwith, A. L. J.; Bowry, V. W.; Bowman, W. R.; Mann, E.; Parr, J.; Storey, J. M. D. Angew. Chem., Int. Ed. 2004, 43, 95
54. Jia, Y. X.; Kündig, E. P. Angew. Chem., Int. Ed. 2009, 48, 1636
55. Jia, Y. X.; Katayev, D.; Bernardinelli, G.; Siedel, T. M.; Kündig, E. P. Chem. Eur. J. 2010, 16, 6300
56. Liu, C.; Liu, D.; Zhang, W.; Zhou, L.; Lei, A. Org. Lett. 2013, 15, 6166
57. More references on oxindole synthesis by C-H functionalization: Dey, C.; Larionov, E.; Kündig, E. P. Org. Biomol. Chem. 2013, 11, 6734
58. Snieckus, V. Chem. Rev. 1990, 90, 879-933
59. Tsukazaki, M.; Roglans, A.; Chapell, B. J.; Taylor, N. J.; Snieckus, V. J. Am. Chem. Soc. 1996, 118, 685
60. Laufer, R. S.; Veith, U.; Taylor, N. J.; Snieckus, V. Org. Lett. 2000, 2, 629
61. Kumar, S.; Singh, H. B.; Wolmershäuser, G. Organometallics 2006, 25, 382
62. Kumar, S.; Helt, J.-C. P.; Autschbach, J.; Detty, M. R. Organometallics 2009, 28, 3426
63. Rousseaux, S.; Gorelsky, S. I.; Chung, B. K. W.; Fagnou, K. J. Am. Chem. Soc. 2010, 132, 10692
64. Balkrishna, S. J; Bhakuni, B. S.; Chopra, D.; Kumar, S. Org. Lett. 2010, 12, 5394
65. Balkrishna, S. J.; Bhakuni, B. S.; Kumar, S. Tetrahedron 2011, 67, 9565
66. Bhakuni, B. S.; Balkrishna, S. J.; Kumar, A.; Kumar, S. Tetrahedron Lett. 2012, 53, 1354
67. For biaryl coupling reactions with 2-halobenzamides, see refs 2d,2e and 3c
68. Deprez, P.; Guillaume, J.; Becker, R.; Corbier, A.; Didierlaurent, S.; Fortin, M.; Frechet, D.; Hamon, G.; Heckmann, B.; Heitsch, H.; Kleemann, H. W.; Vevert, J. P.; Vincent, J. C.; Wagner, A.; Zhang, J. D. J. Med. Chem. 1995, 38, 2357
69. Markham, A.; Goa, K. L. Drugs 1997, 54, 299
70. James, C. A.; Snieckus, V. Tetrahedron Lett. 1997, 38, 8149
71. Sharpe, M.; Jarvis, B.; Goa, K. L. Drugs 2001, 61, 1501
72. Malmström, J.; Jonsson, M.; Cotgreave, I. A.; Hammarström, L.; Sjödin, M.; Engman, L. J. Am. Chem. Soc. 2001, 123, 3434
73. Shanks, D.; Amorati, R.; Fumo, M. G.; Pedulli, G. F.; Valgimigli, L.; Engman, L. J. Org. Chem. 2006, 71, 1033
74. Amorati, R.; Valgimigli, L.; Dinér, P.; Bakhtiari, K.; Saeedi, M.; Engman, L. Chem. Eur. J. 2013, 19, 7513
75. Singh, V. P.; Poon, J.-f.; Engman, L. Org. Lett. 2013, 15, 6274
76. Fabrycy, A.; Kosmider, A. Rocz. Chem. 1973, 47, 937
77. Bailey, D. M.; Grazia, D.; George, C. J. Org. Chem. 1970, 35, 4093
78. Campbell, J. B.; Dedinas, R. F.; Trumbower-Walsh, S. A. J. Org. Chem. 1996, 61, 6205
79. Kundu, N. G.; Khan, M. W. Tetrahedron 1969, 6, 475
80. Mao, C.-Z.; Barnish, I. T.; Charles, R. J. Heterocycl. Chem. 1969, 6, 475
81. He, Z.; Yudin, A. K. Org. Lett. 2006, 8, 5829
82. Schroeder, N.; Wencel, D.; Glorius, F. J. Am. Chem. Soc. 2012, 134, 8298
83. Balloch, L.; Kennedy, A. R.; Mulvey, R. E.; Rantanen, T.; Robertson, S. D.; Snieckus, V. Organometallics 2011, 30, 145
84. Chan, V. S.; Bergman, R. G.; Toste, F. D. J. Am. Chem. Soc. 2007, 129, 15122
85. Maji, M. S.; Murarka, S.; Studer, A. Org. Lett. 2010, 12, 3879
86. Barrett, K. T.; Miller, S. J. J. Am. Chem. Soc. 2013, 135, 2963
87. Thirunavukkarasu, V. S.; Hubrich, J.; Ackermann, L. Org. Lett. 2012, 14, 4210