Mild and efficient allylation of aldehydes by using copper fluorapatite as catalyst

Advanced Synthesis and Catalysis

Volumn 350, Issue 10, 2008, Pages 1497-1502

  Lakshmi Kantam, M ^a   Venkanna, G T ^a   Shiva Kumar, K B ^a   Balasubrahmanyam, V ^a   Venkateswarlu, G ^a   Sreedhara, B ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Aldehydes; Allylation; Copper fluorapatite; Homoallylic alcohols

Indexed keywords

EID: 53849099291     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200800159     Document Type: Article

References (88)

1. a) J. A. Marshall, Chem. Rev. 2000, 100, 3163;
2. b) J. A. Marshall, Chem. Rev. 1996, 96, 31.
3. a) Y. Yamamoto, N. Asao, Chem. Rev. 1993, 93, 2207;
4. b) D. Hoppe, in: Houben-Weyl; Methods of Organic Chemistry, (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E Schaumann), Thieme, Stuttgart, New York, Vol. E21, 1996, p 1357;
5. c) J. W. J. Kennedy, D. G. Hall, Angew. Chem. 2003, 115, 4880;
6. Angew. Chem. Int. Ed. 2003, 42, 4732.
7. a) T. Akiyama, J. Iwai, Synlett 1998, 273;
8. b) S. Istuno, K. Watanable, K. Ito A. A. El-Shehawy, A. A. Sarhan, Angew. Chem. 1997, 109, 105;
9. Angew. Chem. Int. Ed. Engl. 1997, 36, 109;
10. c) H. Nakamura, H. Iwama, Y. Yamamoto, J. Am. Chem. Soc. 1996, 118, 6641;
11. d) A. Yanagisawa, H. Nakashima, A. Ishiba, H. Yamamoto, J. Am. Chem. Soc. 1996, 118, 4723;
12. e) G. E. Keck, K. H. Tarbet, L. S. Geraci, J. Am. Chem. Soc. 1993, 115, 8467.
13. H. R. Kalita, A. J. Borah, P. Phukan, Tetrahedron Lett. 2007, 48, 5047.
14. N. S. Krishnaveni, K. Surendra, V. P. Kumar, B. Srinivas, C. Suresh Reddy, K. Rama Rao, Tetrahedron Lett. 2005, 46, 4299.
15. J. Lu, S.-J. Ji, R. Qian, J.-P. Chen, Y. Liu, T.-P. Loh, Synlett 2004, 534.
16. B. M. Choudary, K. Jyothi, M. Sateesh, M. L. Kantam, Synlett 2004, 231.
17. a) A. S.-Y. Lee, S.-F. Chu, Y.-T. Chang, S.-H. Wang, Tetrahedron Lett. 2004, 45 1551;
18. b) J. Legros, F. Meyer, M. Coliboeuf, B. Crousse, D. Bonnet-Delpon, J.-P. Begue, J. Org. Chem. 2003, 68, 6444;
19. c) J. Zhang, P. G. Blazecka, H. Berven, D. Belmont, Tetrahedron Lett. 2003, 44, 5579;
20. d) S. Wada, N. Hayashi, H. Suzuki, Org. Biomol. Chem. 2003, 1, 2160;
21. e) D. R. Williams, A. A. Kiryanov, U. Emde, M. P. Clark, M. A. Berliner, J. T. Reeves, Angew. Chem. 2003, 115, 1296;
22. Angew. Chem. Int. Ed. 2003, 42, 1258;
23. f) C. C. K. Keh, C. Wei, C.-J. Li, J. Am. Chem. Soc. 2003, 125, 4062;
24. g) M.-I. Lannou, F. Helion, J.-L. Namy, Tetrahedron Lett. 2002, 43, 8007.
25. a) J. Nokami, J. Otera, T. Sudo, R. Okawara, Organometallics 1983, 2, 191;
26. b) M. Wada, H. Ohki, K. Akiba, J. Chem. Soc. Chem. Commun. 1987, 708;
27. c) R. Khan, R. Prasada, S. Turga, J. Chem. Res. (S) 1998, 202;
28. d) H. Tanaka, S. Nakahata, H. Watanabe, J. Zhao, M. Kuroboshi, S. Torii, Inorg. Chim. Acta 1999, 296, 204;
29. e) I. S. Estevam, L. W. Bieber, Tetrahedron Lett. 2003, 44, 667.
30. a) M. Wada, T. Fukuma, M. Morioka, T. Takahashi, N. Miyoshi, Tetrahedron Lett. 1997, 38, 8045;
31. b) C.-J Li, W.-C. Zhang, J. Am. Chem. Soc. 1998, 120, 9102;
32. c) W.-C. Zhang, C.-J. Li, J. Org. Chem. 1999, 64, 3230;
33. d) P. Lucas, J. Gajewski, T. H. Chan, Can. J. Anal. Sci. Spectrosc. 2003, 48, 1.
34. a) C.-J. Li, Y. Meng, X.-H. Yi, J. Ma, T.-H. Chan, J. Org. Chem. 1998, 63, 7498;
35. b) C.-J. Li, Y. Meng, X.-H. Yi, J. Ma, T.-H. Chan, J. Org. Chem. 1997, 62, 8632.
36. a) T. H. Chan, C. J. Li, M. C. Lee, Z. Y. Wei, Can. J. Chem. 1994, 72, 1181;
37. b) P. Cintas, Synlett 1995, 1087;
38. c) L. A. Paquette, T. M. Mitzel, J. Am. Chem. Soc. 1996, 118, 1931;
39. d) Y. H. Chan, Y. Yang, J. Am. Chem. Soc. 1999, 121, 3228;
40. e) T. P. Loh, J. R. Zhou, Z. Yin, Org. Lett. 1999, 1, 1855;
41. f) Y.-F. Yuan, Z. Cao, A.-G. Hu, J.-T. Wang, Chin. J. Org. Chem. 2000, 20, 269;
42. g) G. Hilt, K. Ismolko, C. Waloch, Tetrahedron Lett. 2002, 43, 1437;
43. h) K.-T. Tan, S.-S. Chng, H.-S. Cheng, T.-P. Loh, J. Am. Chem. Soc. 2003, 125, 2958.
44. a) W. Wang, L. Shi, Y. Huang, Tetrahedron 1990, 46, 3315;
45. b) P.-D. Ren, Q.-H. Jin, Z.-P. Yao, Synth. Commun. 1997, 27, 2761;
46. c) L.-H. Li, T. H. Chan, Tetrahedron Lett. 2000, 41, 5009;
47. d) L.-H. Li, T. H. Chan, Can. J. Chem. 2001, 79, 1536.
48. a) M. Minato, J. Tsuji, Chem. Lett. 1988, 2049;
49. b) M. Wada, H. Ohki, K. Y. Akiba, Bull. Chem. Soc. Jpn. 1990, 63, 2751;
50. c) P.-D. Ren, S.-F. Pan, T.-W. Dong, S.-H. Wu, Chin. J. Chem. 1996, 14, 462;
51. d) D. Laskar, M. Gohain, D. Prajapati, J. S. Sandhu, New J. Chem. 2002, 26, 193;
52. e) J.-Y. Zhou, G.-F. Sun, M.-F. Zhang, Y. Jia, S.-H. Wu, Chin. J. Chem. 1997, 15, 361.
53. J.-Y. Zhou, G.-F. Sun, M.-F. Zhang, Y. Jia, S.-H. Wu, Chin. J. Chem, 1997, 15, 361.
54. a) Z. Wang, S. Yuan, C.-J. Li, Tetrahedron Lett. 2002, 43, 5097;
55. b) Z.-Y. Wang, S.-Z. Yuan, Z.-G. Zha, Z.-D. Zhang, Chin. J. Chem. 2003, 21, 1231.
56. a) C. Petrier, J. L. Luche, J. Org. Chem. 1985, 50, 910;
57. b) D. Deng, Z. Lu, Chin. Chem. Lett. 1994, 5, 173;
58. c) D.-L. Deng, Z.-H. Lu, K. Wu, Chin. J. Org. Chem. 1996, 16, 462;
59. d) D. Marton, D. Stivanello, G. Tagliavini, J. Org. Chem. 1996, 61, 2731;
60. e) X. Yi, J. X. Haberman, C. J. Li, Synth. Commun. 1998, 28 , 2999;
61. f) Z.-G. Zha, Z. Xie, C.-L. Zhou, Z.-Y. Wang, Y.-S. Wang, Chin. J. Chem. 2002, 20, 1477;
62. g) W. Chung, S. Higashiya, Y. Oba, J. T. Welch, Tetrahedron 2003, 59, 10031;
63. h) Z. Zha, Z. Xie, C. Zhou, M. Chang, Z. Wang, New J. Chem. 2003, 27, 1297.
64. a) T. Mukaiyama, T. Harada, Chem. Lett. 1981, 1527;
65. b) S. Wu, T. Zhu, Acta Chim. Sin. 1987, 45, 1135;
66. c) S. H. Wu, B. Z. Huang, T. M. Zhu, D. Z. Yiao, Y. L. Chu, Acta Chim. Sin. 1990, 48, 372;
67. d) J.-Y. Zhou, Z.-G. Chen, Y. Jia, S.-H. Wu, Acta Chim. Sin. 1998, 56, 93;
68. e) T. H. Chan, Y. Yang, C. J. Li, J. Org. Chem. 1999, 64, 4452;
69. f) C.-L. Zhou, Z.-G. Zha, Z.-Y. Wang, J.-H. Wu, J.-H. Zhang, Chin. J. Chem. 2002, 20, 718.
70. a) P. Sinha, S. Roy, Chem. Commun. 2001, 1798;
71. b) P. Sinha, S. Roy, Organometallics 2004, 23, 67;
72. c) A. Kundu, S. Prabhakar, M. Vairamani, S. Roy, Organometallics 1997, 16, 4796.
73. a) X. H. Tan, Y. Q. Hou, C. Huang, L. Liu, Q. X. Guo, Tetrahedron 2004, 60, 6129;
74. b) X. H. Tan, Y. Q. Hou, B. Shen, L. Liu, Q. X. Guo, Tetrahedron Lett. 2004, 45, 5525.
75. S. Sugiyama, T. Minami, H. Hayashi, M. Tanaka, N. Shigemoto, J. B. Moffat, J. Chem.Soc., Faraday Trans. 1996, 92, 293.
76. a) K. Yamaguchi, K. Mori, T. Mizugaki, K. Ebitani, K. Kaneda, J. Am. Chem. Soc. 2000, 122, 7144;
77. b) K. Mori, K. Yamaguchi, T. Mizugaki, K. Ebitani, K. Kaneda, Chem. Commun. 2001, 461;
78. c) K. Mori, K. Yamaguchi, T. Mizugaki, K. Ebitani, K. Kaneda, New J. Chem. 2002, 26, 1536;
79. d) K. Mori, K. Yamaguchi, T. Hara, T. Mizugaki, K. Ebitani, K. Kaneda, J. Am. Chem. Soc. 2002, 124, 11572;
80. e) K. Mori, T. Hara, M. Oshiba, T. Mizugaki, K. Ebitani, K. Kaneda, New J. Chem. 2005, 29, 1174.
81. a) B. M. Choudary, Ch. Sridhar, M. L. Kantam, G. T. Venkanna, B. Sreedhar, J. Am. Chem. Soc. 2005, 127, 9948;
82. b) M. L. Kantam, G. T. Venkanna, Ch. Sridhar, K. B. Shiva Kumar, Tetrahedron Lett. 2006, 47, 3897;
83. c) M. L. Kantam, G. T. Venkanna, Ch. Sridhar, B. Sreedhar, B. M. Choudary, J. Org. Chem. 2006, 71, 9522;
84. d) M. L. Kantam, K. B. Shiva Kumar, P. Srinivas, B. Sreedhar, Adv. Synth. Catal. 2007, 349, 1141.
85. S. Sebti, R. Nazih, R. Tahir, L. Salhi, A. Saber, Appl. Catal. 2000, 197, 187.
86. L. Liu, J. Sun, N. Liu, W. Chang, J. Li, Tetrahedron: Asymmetry 2007, 18, 710.
87. G. Bartoli, M. Bosco, A. Giuliani, E. Marcantoni, A. Palmieri, M. Petrini, L. Sambri, J. Org. Chem. 2004, 69, 1290.
88. Q. Chai, C. Song, Z. Sun, Y. Ma, C. Ma, Y. Dia, M. Andrus, Tetrahedron Lett. 2006, 47, 8611.