Synthesis of water-tolerant indium homoenolate in aqueous media and its application in the synthesis of 1,4-dicarbonyl compounds via palladium-catalyzed coupling with acid chloride

Journal of the American Chemical Society

Volumn 132, Issue 45, 2010, Pages 15852-15855

  Shen, Zhi Liang ^a   Goh, Kelvin Kau Kiat ^a   Cheong, Hao Lun ^a   Wong, Colin Hong An ^a   Lai, Yin Chang ^a   Yang, Yong Sheng ^a   Loh, Teck Peng ^a  

^a Nanyang Technological University   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

ACID CHLORIDES; AQUEOUS MEDIA; CATALYZED COUPLING; DICARBONYL COMPOUNDS; OXIDATIVE ADDITIONS; SYNTHETIC UTILITY;

ACIDS; CATALYSIS; CHLORINE COMPOUNDS; COMPLEXATION; INDIUM; KETONES; PALLADIUM; SYNTHESIS (CHEMICAL);

INDIUM COMPOUNDS;

1,2 DICARBONYL DERIVATIVE; 1,4 DICARBONYL COMPOUND; CHLORIDE; INDIUM; INDIUM CHLORIDE IN 111; INDIUM HOMOENOLATE; KETONE; PALLADIUM; UNCLASSIFIED DRUG; WATER;

ADDITION REACTION; AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; OXIDATION REDUCTION POTENTIAL; SYNTHESIS;

EID: 78449251148     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja106925f     Document Type: Article

References (107)

1. For reviews concerning homoenolate chemistry, see
2. Werstiuk, N. H. Tetrahedron 1983, 39, 205
3. Hoppe, D. and Hense, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2282
4. Hoppe, D., Marr, F., and Bruggemann, M. Top. Organomet. Chem. 2003, 5, 61
5. Kuwajima, I. and Nakamura, E. In Comprehensive Organic Synthesis; Trost, B. M. and Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 2, p 441 and references cited therein.
6. Kuwajima, I. and Nakamura, E. In Topics in Current Chemistry; Springer: Berlin, 1990; Vol. 155, p 3.
7. Nakamura, E. and Kuwajima, I. J. Am. Chem. Soc. 1977, 99, 7360
8. Nakamura, E. and Kuwajima, I. J. Am. Chem. Soc. 1984, 106, 3368
9. Nakamura, E., Shimada, J.-i., and Kuwajima, I. Organometallics 1985, 4, 641
10. Oshino, H., Nakamura, E., and Kuwajima, I. J. Org. Chem. 1985, 50, 2802
11. Nakamura, E., Oshino, H., and Kuwajima, I. J. Am. Chem. Soc. 1986, 108, 3745
12. Nakamura, E., Aoki, S., Sekiya, K., Oshino, H., and Kuwajima, I. J. Am. Chem. Soc. 1987, 109, 8056
13. Nakamura, E. and Kuwajima, I. J. Am. Chem. Soc. 1985, 107, 2138
14. Horiguehi, Y., Nakamura, E., and Kuwajima, I. J. Org. Chem. 1986, 51, 4323
15. Nakamura, E. and Kuwajima, I. J. Am. Chem. Soc. 1983, 105, 651
16. For the X-ray analysis of a titanium homoenolate, see
17. Cozzi, P. G., Carofiglio, T., and Floriani, C. Organometallics 1993, 12, 2845
18. Tamaru, Y., Ochiai, H., Nakamura, T., and Yoshida, Z. Angew. Chem., Int. Ed. Engl. 1987, 26, 1157
19. Tamaru, Y., Ochiai, H., Nakamura, T., and Yoshida, Z. Tetrahedron Lett. 1986, 27, 955
20. Tamaru, Y., Ochiai, H., Nakamura, T., Tsubaki, K., and Yoshida, Z. Tetrahedron Lett. 1985, 26, 5559
21. Ochiai, H., Tamaru, Y., Tsubaki, K., and Yoshida, Z. J. Org. Chem. 1987, 52, 4418
22. For other selected typical methods for the synthesis of metal homoenolate by Knochel et al., see
23. Sidduri, A., Rozema, M. J., and Knochel, P. J. Org. Chem. 1993, 58, 2694
24. Still, W. C. J. Am. Chem. Soc. 1978, 100, 1481
25. Goswami, R. J. Org. Chem. 1985, 50, 5907
26. For reviews regarding the generation of a homoenolate intermediate with the use of NHC catalysis, see
27. Nair, V., Vellalath, S., and Babu, B. P. Chem. Soc. Rev. 2008, 37, 2691
28. For recent examples, see
29. Sohn, S. S., Rosen, E. L., and Bode, J. W. J. Am. Chem. Soc. 2004, 126, 14370
30. Burstein, C. and Glorius, F. Angew. Chem., Int. Ed. 2004, 43, 6205
31. He, M. and Bode, J. W. Org. Lett. 2005, 7, 3131
32. Nair, V., Vellalath, S., Poonoth, M., Mohan, R., and Suresh, E. Org. Lett. 2006, 8, 507
33. Nair, V., Poonoth, M., Vellalath, S., Suresh, E., and Thirumalai, R. J. Org. Chem. 2006, 71, 8964
34. Nair, V., Vellalath, S., Poonoth, M., and Suresh, E. J. Am. Chem. Soc. 2006, 128, 8736
35. Phillips, E. M., Wadamoto, M., Chan, A., and Scheidt, K. A. Angew. Chem., Int. Ed. 2007, 46, 3107
36. Chiang, P.-C., Kaeobamrung, J., and Bode, J. W. J. Am. Chem. Soc. 2007, 129, 3520
37. Wadamoto, M., Phillips, E. M., Reynolds, T. E., and Scheidt, K. A. J. Am. Chem. Soc. 2007, 129, 10098
38. He, M. and Bode, J. W. J. Am. Chem. Soc. 2008, 130, 418
39. Nair, V., Babu, B. P., Vellalath, S., and Suresh, E. Chem. Commun. 2008, 747
40. Chan, A. and Scheidt, K. A. J. Am. Chem. Soc. 2007, 129, 5334
41. Phillips, E. M., Reynolds, T. E., and Scheidt, K. A. J. Am. Chem. Soc. 2008, 130, 2416
42. Chan, A. and Scheidt, K. A. J. Am. Chem. Soc. 2008, 130, 2740
43. Seayad, J., Patra, P. K., Zhang, Y., and Ying, J. Y. Org. Lett. 2008, 10, 953
44. Sohn, S. S. and Bode, J. W. Org. Lett. 2005, 7, 3873
45. He, M., Struble, J. R., and Bode, J. W. J. Am. Chem. Soc. 2006, 128, 8418
46. Takami, K., Yorimitsu, H., Shinokubo, H., Matsubara, S., and Oshima, K. Org. Lett. 2001, 3, 1997
47. For the recent development of aryl and benzyl indium reagents which were pioneered by Knochel et al., see
48. Chen, Y. H. and Knochel, P. Angew. Chem., Int. Ed. 2008, 47, 7648
49. Chen, Y. H., Sun, M., and Knochel, P. Angew. Chem., Int. Ed. 2009, 48, 2236
50. Papoian, V. and Minehan, T. J. Org. Chem. 2008, 73, 7376
51. Chupak, L. S., Wolkowski, J. P., and Chantigny, Y. A. J. Org. Chem. 2009, 74, 1388
52. Fujiwara, N. and Yamamoto, Y. J. Org. Chem. 1999, 64, 4095
53. Organic reactions in water; for reviews, see
54. Li, C. J. and Chan, T. H. Tetrahedron 1999, 55, 11149
55. Li, C. J. Chem. Rev. 2005, 105, 3095
56. Li, C. J. Chem. Rev. 1993, 93, 2023
57. Li, C. J. and Chen, L. Chem. Soc. Rev. 2006, 35, 68
58. Dallinger, D. and Kappe, C. O. Chem. Rev. 2007, 107, 2563
59. Kobayashi, S. and Manabe, A. K. Acc. Chem. Res. 2002, 35, 209
60. Lindstrom, U. M. Chem. Rev. 2002, 102, 2751
61. Li, C. J. Acc. Chem. Res. 2002, 35, 533
62. Li, C. J. Green Chem. 2002, 4, 1
63. Miyabe, H. and Naito, T. Org. Biomol. Chem. 2004, 2, 1267
64. Herrerías, C. I., Yao, X. Q., Li, Z. P., and Li, C. J. Chem. Rev. 2007, 107, 2546
65. Chauhan, K. K. and Frost, C. G. J. Chem. Soc., Perkin Trans. 1 2000, 3015
66. Babu, G. and Perumal, P. T. Aldrichimica Acta 2000, 33, 16
67. For the formation of nickel-π-allyl complexes via oxidative addition of nickel(0) to enones in the presence of Lewis acids, see
68. Johnson, J. R., Tully, P. S., Mackenzie, P. B., and Sabat, M. J. Am. Chem. Soc. 1991, 113, 6172
69. Grisso, B. A., Johnson, J. R., and Mackenzie, P. B. J. Am. Chem. Soc. 1992, 114, 5160
70. For our previous works on the development of Barbier-Grignard-type alkylation reaction of imine, aldehyde, nitrone, and α,β-unsaturated carbonyl compounds in aqueous media using In/CuI via a radical type mechanism, see
71. Shen, Z. L. and Loh, T. P. Org. Lett. 2007, 9, 5413
72. Shen, Z. L., Cheong, H. L., and Loh, T. P. Chem.-Eur. J. 2008, 14, 1875
73. Shen, Z. L., Yeo, Y. L., and Loh, T. P. J. Org. Chem. 2008, 73, 3922
74. Yang, Y. S., Shen, Z. L., and Loh, T. P. Org. Lett. 2009, 11, 1209
75. Shen, Z. L., Cheong, H. L., and Loh, T. P. Tetrahedron Lett. 2009, 50, 1051
76. For a review of our previous works on indium, see
77. Loh, T. P. and Chua, G. L. Chem. Commun. 2006, 2739
78. Similar results regarding the synthesis of β,γ-unsaturated ketone has already been reported by Kim and co-workers
79. Kang, S., Jang, T. S., Keum, G., Kang, S. B., Han, S. Y., and Kim, Y. Org. Lett. 2000, 2, 3615
80. 2O by our group, see
81. Yang, Y. S., Shen, Z. L., and Loh, T. P. Org. Lett. 2009, 11, 2213
82. For selected examples of organoindium complexes, see
83. Yasuda, M., Haga, M., and Baba, A. Organometallics 2009, 28, 1998
84. Yasuda, M., Kiyokawa, K., Osaki, K., and Baba, A. Organometallics 2009, 28, 132
85. Nishimoto, Y., Moritoh, R., Yasuda, M., and Baba, A. Angew. Chem., Int. Ed. 2009, 48, 4577
86. 2O (1:1) also produced the α-deuterated indium homoenolate in a similar yield of 81%.
87. DeMartino, M. P., Chen, K., and Baran, P. S. J. Am. Chem. Soc. 2008, 130, 11546 and references cited therein
88. See the Supporting Information for details of the optimization of reaction conditions for palladium-catalyzed coupling of indium homoenolate with acid chloride using various organic solvents and palladium catalysts.
89. 3) in palladium-catalyzed coupling reactions by Sarandeses et al., see
90. Pérez, I., Sestelo, J. P., and Sarandeses, L. A. J. Am. Chem. Soc. 2001, 123, 4155
91. 3In or other types of organoindium reagents with various electrophiles (such as ArX, acid chloride, benzyl halides, alkenyl halides), see: Caeiro, J., Sestelo, J. P., and Sarandeses, L. A. Chem.-Eur. J. 2008, 14, 741
92. Pena, M. A., Pérez, I., Sestelo, J. P., and Sarandeses, L. A. Chem. Commun. 2002, 2246
93. Nomura, R., Miyazaki, S.-I., and Matsuda, H. J. Am. Chem. Soc. 1992, 114, 2738
94. Lee, P. H., Sung, S., and Lee, K. Org. Lett. 2001, 3, 3201
95. Pena, M. A., Sestelo, J. P., and Sarandeses, L. A. Synthesis 2003, 780
96. Gotov, B., Kaufmann, J., Schumann, H., and Schmalz, H. G. Synlett 2002, 361
97. Jaber, N., Gelman, D., Schumann, H., Dechert, S., and Blum, J. Eur. J. Org. Chem. 2002, 1628
98. Lee, K., Lee, J., and Lee, P. H. J. Org. Chem. 2002, 67, 8265
99. Lee, K., Seomoon, D., and Lee, P. H. Angew. Chem., Int. Ed. 2002, 41, 3901
100. Takami, K., Yorimitsu, H., and Oshima, K. Org. Lett. 2002, 4, 2993
101. Lee, P. H., Lee, S. W., and Lee, K. Org. Lett. 2003, 5, 1103
102. Takami, K., Mikami, S., Yorimitsu, H., Shinokubo, H., and Oshima, K. J. Org. Chem. 2003, 68, 6627
103. Lee, P. H., Lee, S. W., and Seomoon, D. Org. Lett. 2003, 5, 4963
104. Pena, M. A., Sestelo, J. P., and Sarandeses, L. A. Synthesis 2005, 485
105. Pena, M. A., Sestelo, J. P., and Sarandeses, L. A. J. Org. Chem. 2007, 72, 1271
106. Font-Sanchis, E., Céspedes-Guirao, F. J., Sastre-Santos, Á., and Fernández-Lázaro, F. J. Org. Chem. 2007, 72, 3589
107. Riveiros, R., Saya, L., Sestelo, J. P., and Sarandeses, L. A. Eur. J. Org. Chem. 2008, 1959