The new world of organic reactions in water

Pure and Applied Chemistry

Volumn 85, Issue 6, 2013, Pages 1089-1101

  Kobayashi, Shu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Allylation; Allylic amination; Asymmetric catalysis; C C bond formation; Green sustainable chemistry; Water

Indexed keywords

ALLYLIC AMINATION; AQUEOUS AMMONIA; ASYMMETRIC CATALYSIS; C-C BOND FORMATION; DIASTEREO- AND ENANTIOSELECTIVITY; GREEN SUSTAINABLE CHEMISTRIES; ORGANIC REACTION; PALLADIUM-CATALYZED;

ALLYLATION; AMMONIA; CATALYSIS; CHEMICAL BONDS; KETONES; ORGANIC SOLVENTS; WATER;

AMINES;

EID: 84878831765     PISSN: 00334545     EISSN: 13653075     Source Type: Journal    
DOI: 10.1351/PAC-CON-12-10-11     Document Type: Article

References (106)

1. C.-J. Li. Chem. Rev. 105, 3095 (2005)
2. U. M. Lindstroem (Ed.). Organic Reactions in Water, Wiley-Blackwell, Oxford (2007)
3. S. Kobayashi (Ed.). Water in Organic Synthesis (Science of Synthesis), Thieme, Stuttgart (2012).
4. D. C. Rideout, R. Breslow. J. Am. Chem. Soc. 102, 7816 (1980)
5. H. Yorimitsu, T. Nakamura, H. Shinikubo, K. Oshima, K. Omoto, H. Fujimoto. J. Am. Chem. Soc. 122, 11041 (2000)
6. S. Narayan, J. Muldoon, M. G. Finn, V. V. Fokin, H. C. Kolb, K. B. Sharpless. Angew. Chem., Int. Ed. 44, 3275 (2005)
7. L. Ackermann, J. Pospech. Org. Lett. 13, 4153 (2011);
8. T. Kitanosono, M. Sakai, M. Ueno, S. Kobayashi. Org. Biomol. Chem. 10, 7134 (2012).
9. S. Kobayashi. In Water in Organic Synthesis (Science of Synthesis), S. Kobayashi (Ed.), pp. 855-867, Thieme, Stuttgart (2012).
10. For general overview on allylic amination, see: S. A. Godleski. In Comprehensive Organic Synthesis, Vol. 4, B. M. Trost (Ed.), p. 585, Pergamon, Oxford (1991)
11. M. Johannsen, K. A. Jørgensen. Chem. Rev. 98, 1689 (1998)
12. B. M. Trost, D. L. Van Vraken. Chem. Rev. 96, 395 (1996)
13. B. M. Trost. Chem. Pharm. Bull. 50, 1 (2002)
14. B. M. Trost, M. L. Crawley. Chem. Rev. 103, 2921 (2003)
15. H. Miyabe, Y. Takemoto. Synlett 1641 (2005)
16. Z. Lu, S. Ma. Angew. Chem., Int. Ed. 47, 258 (2008).
17. Recently, growing attention has been paid to direct use of ammonia as a nitrogen source for organic synthesis, see: B. Zimmermann, J. Herwig, M. Beller. Angew. Chem., Int. Ed. 38, 2372 (1999)
18. F. Lang, D. Zewge, I. N. Houpis, R. P. Volante. Tetrahedron Lett. 42, 3251 (2001)
19. T. Gross, A. M. Seayad, M. Ahmad, M. Beller. Org. Lett. 4, 2055 (2002)
20. B. Miriyala, S. Bhattacharyya, J. S. Williamson. Tetrahedron 60, 1463 (2004)
21. B. Dhudshia, J. Tiburcio, A. N. Thadani. Chem. Commun. 5551 (2005)
22. Q. Shen, J. F. Hartwig. J. Am. Chem. Soc. 128, 10028 (2006)
23. D. S. Surry, S. L. Buchwald. J. Am. Chem. Soc. 129, 10354 (2007)
24. M. J. Pouy, A. Leitner, D. J. Weix, S. Ueno, J. F. Hartwig. Org. Lett. 9, 3949 (2007)
25. C. Varszegi, M. Ernst, F. van Laar, B. F. Sels, E. Schwab, D. E. De Vos. Angew. Chem., Int. Ed. 47, 1477 (2008)
26. C. Gunanathan, D. Milstein. Angew. Chem., Int. Ed. 47, 8661 (2008)
27. J. Kim, S. Chang. Chem. Commun. 3052 (2008)
28. N. Xia, M. Taillefer. Angew. Chem., Int. Ed. 48, 337 (2009). See also ref. [10].
29. Hartwig reported Ir-catalyzed allylic amination of methyl cinnamyl carbonate using a dioxane solution of ammonia gave the corresponding secondary amine exclusively, see ref. [2h]. After our first report (ref. [4]), his group reported the use of ammonia in enantioselective Ir-catalyzed monoallylation. M. J. Pouy, L. M. Stanley, J. F. Hartwig. J. Am. Chem. Soc. 131, 11312 (2009).
30. T. Nagano, S. Kobayashi. J. Am. Chem. Soc. 131, 4200 (2009).
31. B. M. Trost, E. Keinan. J. Org. Chem. 44, 3451 (1979).
32. S. E. Byström, R. Aslanian, J.-E. Bäckvall. Tetrahedron Lett. 26, 1749 (1985).
33. Y. Inoue, M. Taguchi, M. Toyofuku, H. Hashimoto. Bull. Chem. Soc. Jpn. 57, 3021 (1984).
34. R. D. Connell, T. Rein, B. Åkermark, P. Helquist. J. Org. Chem. 53, 3845 (1988).
35. S.-I. Murahashi, Y. Taniguchi, Y. Imada, Y. Tanigawa. J. Org. Chem. 54, 3292 (1989).
36. Recent examples, see: R. Weihofen, O. Tverskoy, G. Helmchen. Angew. Chem., Int. Ed. 45, 5546 (2006)
37. C. Defieber, M. A. Ariger, P. Moriel, E. M. Carreira. Angew. Chem., Int. Ed. 46, 3139 (2007). See also ref. [1b].
38. M. Sugiura, K. Hirano, S. Kobayashi. J. Am. Chem. Soc. 126, 7182 (2004)
39. S. Kobayashi, K. Hirano, M. Sugiura. Chem. Commun. 104 (2005)
40. M. Sugiura, K. Hirano, S. Kobayashi. Org. Synth. 83, 170 (2005).
41. Unpublished.
42. D. Smyth, H. Tye, C. Eldred, N. W. Alcock, M. Wills. J. Chem. Soc., Perkin Trans. 1 2840 (2001).
43. M. Yamaguchi, M. Yabuki, T. Yamagishi, K. Sakai, T. Tsubomura. Chem. Lett. 241 (1996)
44. H. Kodama, T. Taiji, T. Ohta, I. Furukawa. Synlett 385 (2001).
45. X. Lu, L. Lu, J. Sun. J. Mol. Catal. 41, 245 (1987).
46. th European Symposium on Organic Chemistry, Prague, 14 July 2009.
47. Recently, Oshima and Mashima reported similar results. K. Das, R. Shibuya, Y. Nakahara, N. Germain, T. Ohshima, K. Mashima. Angew. Chem., Int. Ed. 51, 150 (2012); see also
48. M. Utsunomiya, Y. Miyamoto, J. Ipposhi, T. Ohshima, K. Mashima. Org. Lett. 9, 3371 (2007).
49. A. Hosomi, K. Miura. In Comprehensive Organometallic Chemistry III, Vol. 9, P. Knochel (Ed.), p. 297, Elsevier, Oxford (2007).
50. A. Baba, I. Shibata, M. Yasuda. In Comprehensive Organometallic Chemistry III, Vol. 9, P. Knochel (Ed.), p. 341, Elsevier, Oxford (2007).
51. N. Miyaura, Y. Yamamoto. In Comprehensive Organometallic Chemistry III, Vol. 9, P. Knochel (Ed.), p. 145, Elsevier, Oxford (2007).
52. R. W. Hoffmann, H.-J. Zei. J. Org. Chem. 46, 1309 (1981).
53. R. W. Hoffmann, B. Landmann. Chem. Ber. 119, 1039 (1986).
54. J. W. Kennedy, D. G. Hall. J. Am. Chem. Soc. 124, 11586 (2002)
55. T. Ishiyama, T. Ahiko, N. Miyaura. J. Am. Chem. Soc. 124, 12414 (2002)
56. D. G. Hall. Synlett 1644 (2007).
57. In the crotylboration of aldehydes, examples to provide 4-substituted homoallylic alcohols via γ-addition-[3,3]-sigmatropic rearrangement were reported. P. V. Ramachandran, D. Pratihar, D. Biswas. Chem. Commun. 1988 (2005).
58. M. Fujita, T. Nagano, U. Schneider, T. Hamada, C. Ogawa, S. Kobayashi. J. Am. Chem. Soc. 130, 2914 (2008).
59. S. Kobayashi, T. Endo, U. Schneider, M. Ueno. Chem. Commun. 46, 1260 (2010).
60. In the reactions of specific allylstannanes with aldehydes, Α-addition products were obtained in organic solvents in the presence of a stoichiometric amount of a Lewis acid (SnCl4, TiCl4, InCl3).
61. T. Krämer, J.-R. Schwark, D. Hoppe. Tetrahedron Lett. 30, 7037 (1989)
62. J. A. Marshall, K. W. Hinkle. J. Org. Chem. 60, 1920 (1995)
63. D. J. Hallett, E. J. Thomas. Tetrahedron: Asymmetry 6, 2575 (1995)
64. G. W. Bradley, D. J. Hallett, E. J. Thomas. Tetrahedron: Asymmetry 6, 2579 (1995).
65. Crotylzinc·6c complex could be detected by ESI-mass analysis. In the reactions of crotyl boronates with benzaldehyde, background (noncatalyzed) reactions seem to be faster. Boron-zinc transmetalation (from 5 to 9) may be slow due to steric reason. More details are under investigation.
66. S. Kobayashi, T. Endo, M. Ueno. Angew. Chem., Int. Ed. 50, 12262 (2011); see also
67. S. Ishikawa, T. Hamada, K. Manabe, S. Kobayashi. J. Am. Chem. Soc. 126, 12236 (2004)
68. M. Kokubo, T. Naito, S. Kobayashi. Chem. Lett. 38, 904 (2009)
69. M. Kokubo, T. Naito, S. Kobayashi. Tetrahedron 66, 1111 (2010).
70. The examples of catalytic, highly enantioselective allylation of aldehydes in aqueous media are very rare. Cf. S. Kobayashi, N. Aoyama, K. Manabe. Chirality 15, 124 (2003) and refs. cited therein.
71. For the bipyridine chiral ligand, see: C. Bolm, M. Zehnder, D. Bur. Angew. Chem., Int. Ed. 29, 205 (1990)
72. C. Bolm, M. Ewald, M. Felder, G. Schlingloff. Chem. Ber. 125, 1169 (1992)
73. S. Ishikawa, T. Hamada, K. Manabe, S. Kobayashi. Synthesis 2176 (2005).
74. Selected examples for the utility of the resulting tertiary homoallylic alcohols: S. Hayashi, K. Hirano, H. Yorimitsu, K. Oshima. J. Am. Chem. Soc. 128, 2210 (2006)
75. P. Zhao, C. D. Incarvito, J. F. Hartwig. J. Am. Chem. Soc. 128, 9642 (2006)
76. T. Ohmura, H. Furukawa, M. Suginome. J. Am. Chem. Soc. 128, 13366 (2006).
77. K. M. Waltz, J. Gavenonis, P. J. Walsh. Angew. Chem., Int. Ed. 41, 3697 (2002)
78. M. Yasuda, K. Hirata, M. Nishino, A. Yamamoto, A. Baba. J. Am. Chem. Soc. 124, 13442 (2002); key reference for asymmetric In(III) catalysis:
79. J. Lu, M.-L. Hong, S.-J. Ji, Y.-C. Teo, T.-P. Loh. Chem. Commun. 4217 (2005).
80. S. Yamasaki, K. Fujii, R. Wada, M. Kanai, M. Shibasaki. J. Am. Chem. Soc. 124, 6536 (2002)
81. M. Wadamoto, H. Yamamoto. J. Am. Chem. Soc. 127, 14556 (2005); stoichiometric method
82. N. Z. Burns, B. M. Hackman, P. Y. Ng, I. A. Powelson, J. L. Leighton. Angew. Chem., Int. Ed. 45, 3811 (2006).
83. R. Wada, K. Oisaki, M. Kanai, M. Shibasaki. J. Am. Chem. Soc. 126, 8910 (2004)
84. S. Lou, P. N. Moquist, S. E. Schaus. J. Am. Chem. Soc. 128, 12660 (2006).
85. J. J. Miller, M. S. Sigman. J. Am. Chem. Soc. 129, 2752 (2007).
86. Reviews on the stoichiometric use of In(0): B. C. Ranu. Eur. J. Org. Chem. 2347 (2000)
87. V. Nair, S. Ros, C. N. Jayan, B. S. Pillai. Tetrahedron 60, 1959 (2004).
88. rd ed., Oxford Press, Oxford (1998).
89. Selected examples for allylindium reagents: T. H. Chan, Y. Yang. J. Am. Chem. Soc. 121, 3228 (1999)
90. J. G. Lee, K. I. Choi, A. N. Pae, H. Y. Koh, Y. Kang, Y. S. Cho. J. Chem. Soc., Perkin Trans. 1 1314 (2002)
91. G. Fontana, A. Lubineau, M.-C. Scherrmann. Org. Biomol. Chem. 3, 1375 (2005).
92. Reformatsky-type reagents: S. A. Babu, M. Yasuda, I. Shibata, A. Baba. Org. Lett. 6, 4475 (2004).
93. Selected examples for alkyl radical reagents: Account: H. Miyabe, T. Naito. Org. Biomol. Chem. 2, 1267 (2004)
94. Z.-L. Shen, T.-P. Loh. Org. Lett. 9, 5413 (2007).
95. U. Schneider, M. Ueno, S. Kobayashi. J. Am. Chem. Soc. 130, 13824 (2008).
96. In contrast, In(III) complexes are commonly used in catalytic quantities as Lewis acid catalysts: see ref. [28c].
97. Catalytic use of In(0) for the preparation of "allylgallium" from allyl bromide: K. Takai, Y. Ikawa. Org. Lett. 4, 1727 (2002)
98. K. Takai, Y. Ikawa, K. Ishii, M. Kumanda. Chem. Lett. 172 (2002).
99. For In(I) catalysis, U. Schneider, S. Kobayashi. Angew. Chem., Int. Ed. 46, 5909 (2007)
100. U. Schneider, I.-H. Chen, S. Kobayashi. Org. Lett. 10, 737 (2008)
101. S. Kobayashi, H. Konishi, U. Schneider. Chem. Commun. 2313 (2008); application of our In(I) catalysis
102. N. Selander, A. Kipke, S. Sebelius, K. J. Szabó. J. Am. Chem. Soc. 129, 13723 (2007); review on low oxidation state In
103. J. A. J. Pardoe, A. Downs. Chem. Rev. 107, 2 (2007) and refs. cited herein.
104. Optimized conditions: 1 (0.5 mmol), 2 (1.5 equiv), In(0) (3 mol %), H2O (1 m), 30 °C, 24 h. Gallium(0) as a catalyst proved to be much less effective (low yield); the use of allylsilanes did not give any reaction.
105. Single electron transfer (SET) might be facilitated by the low first ionization enthalpy of In (558.3 kj/mol): http://www.webelements.com
106. Account on Lewis and Brønsted acid-catalyzed allylboration of carbonyl compounds: D. G. Hall. Synlett 1644 (2007) and refs. cited herein.