Activation of allyl alcohols as allyl cations, allyl anions, and amphiphilic allylic species by palladium

European Journal of Organic Chemistry

Volumn , Issue 13, 2005, Pages 2647-2656

  Tamaru, Yoshinao ^a  

^a NAGASAKI UNIVERSITY   (Japan)

Author keywords

Allyl alcohols; Allyl anion; Allyl cation; Allylation; Amphiphilic activation; Diethylzinc; Palladium catalysis; Triethylborane ; Umpolung

Indexed keywords

EID: 22144461766     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200500076     Document Type: Article

References (72)

1. J. Tsuji, Transition Metal Reagents and Catalysts, Innovation, in: Organic Synthesis Wiley, Chichester, 2000, chapter 4.
2. Reviews on C1 allylation: a) C. O. Puentes, V. Kouznetsov, J. Heterocycl. Chem. 2002, 39, 595-614;
3. b) S. E. Denmark, N. G. Almstead, in: Modern Carbonyl Chemistry, (Ed.: J. Otera), Wiley-VCH, Weinheim, 2000, Chapter 10;
4. c) S. R. Chemler, R. W. Roush, in: Modern Carbonyl Chemistry, (Ed.: J. Otera), Wiley-VCH, Weinheim, 2000, chapter 11;
5. d) S. Kobayashi, H. Ishitani, Chem. Rev. 1999, 99, 1069-1094.
6. a) H. Nakamura, K. Aoyagi, J.-G. Shim, Y. Yamamoto, J. Am. Chem. Soc. 2001, 123, 372-377;
7. b) Pincer-palladium complexes also promote nucleophilic allylation of aldehydes and imines: N. Solin, J. Kjellgren, K. J. Szabó, J. Am. Chem. Soc. 2004, 126, 7026-7033.
8. In a strict sense, in addition to water, organoboric acids and zinc oxides, regarded as nontoxic, are produced as side products.
9. H. Yorimitsu, T. Nakamura, H. Shinokubo, K. Oshima, K. Omoto, H. Fujimoto, J. Am. Chem. Soc. 2000, 122, 11041-11047.
10. a) K. E. Atkins, W. E. Walker, R. M. Manyik, Tetrahedron Lett. 1970, 11, 3821-3824;
11. b) D. E. Bergbreiter, D. A. Weatherford, J. Chem. Soc. Chem. Commun. 1989, 883-884;
12. c) J. P. Haudegond, Y. Chauvin, D. Commereuc, J. Org. Chem. 1979, 44, 3063-3065.
13. X. Lu, L. Lu, J. Sun, J. Mol. Catal. 1987, 41, 245-251.
14. X. Lu, X. Jiang, X. Tao, J. Organomet. Chem. 1988, 344, 109-118.
15. M. Sakamoto, I. Shimizu, A. Yamamoto, Bull. Chem. Soc. Jpn. 1996, 69, 1065-1078.
16. a) K. Itoh, N. Hamaguchi, M. Miura, M. Nomura, J. Chem. Soc. Perkin Trans. 1 1992, 2833-2835;
17. b) S.-C. Yang, Y.-C. Tsai, Organometallics 2001, 20, 763-770;
18. c) S.-C. Yang, H.-C. Lai, Y.-C. Tsai, Tetrahedron Lett. 2004, 45, 2693-2697.
19. F. Ozawa, H. Okamoto, S. Kawagishi, S. Yamamoto, T. Minami, M. Yoshifuji, J. Am. Chem. Soc. 2002, 124, 10968-10969.
20. a) Y. Tamaru, Y. Horino, M. Araki, S. Tanaka, M. Kimura, Tetrahedron Lett. 2000, 41, 5705-5709;
21. b) M. Kimura, R. Mukai, N. Tanigawa, S. Tanaka, Y. Tamaru, Tetrahedron 2003, 59, 7767-7777.
22. L. H. Toporcer, R. E. Dessy, S. I. E. Green, Inorg. Chem. 1965, 4, 1649-1655.
23. a) U. Kazmaier, F. L. Zumpe, Angew. Chem. Int. Ed. 1999, 38, 1468-1470;
24. b) B. M. Trost, G. M. Schroeder, J. Am. Chem. Soc. 1999, 121, 6759-6760;
25. c) A. Satake, H. Kadohama, H. Koshino, T. Nakata, Tetrahedron Lett. 1999, 40, 3597-3600.
26. Y. Horino, M. Naito, M. Kimura, S. Tanaka, Y. Tamaru, Tetrahedron Lett. 2001, 42, 3113-3116.
27. th edition, Kluwer-Plenum, New York, 2000, p. 144.
28. a) S.-L. You, X.-L. Hou, L.-X. Dai, Z.-Z. Zhu, Org. Lett. 2001, 3, 149-151;
29. b) M. Braun, F. Laicher, T. Meier, Angew. Chem. Int. Ed. 2000, 39, 3494-3497;
30. K. Hiroi, J. Abe, K. Suya, S. Sato, T. Koyama, J. Org. Chem. 1994, 59, 203-213;
31. Y. Huang, X. Lu, Tetrahedron Lett. 1988, 29, 5663-5664;
32. e) S. Murahashi, Y. Makabe, K. Kurita, J. Org. Chem. 1988, 53, 4489-4495.
33. M. Kimura, Y. Horino, R. Mukai, S. Tanaka, Y. Tamaru, J. Am. Chem. Soc. 2001, 123, 10401-10402.
34. M. Kimura, M. Futamata, K. Shibata, Y. Tamaru, Chem. Commun. 2003, 234-235. See also Ref. [10b] and Ref. [10c].
35. th edition, Blackwell Science 2000;
36. b) R. J. Sundberg, Indoles, Academic, 1996.
37. M. Kimura, M. Futamata, R. Mukai, Y. Tamaru, J. Am. Chem. Soc. 2005, 127, 4592-4593.
38. K. M. Depew, S. P. Marsden, D. Zatorska, A. Zatorski, W. G. Bornmann, S. J. Danishefsky, J. Am. Chem. Soc. 1999, 121, 11953-11963.
39. a) F. Hernandez, C. Avendano, M. Söllhuber, Tetrahedron Lett. 2003, 44, 3367-3369;
40. b) G. H. Tan, X. Zhu, A. Ganesan, Org. Lett. 2003, 5, 1801-1803;
41. c) M. S. Morales-Rios, O. R. Suarez-Castillo, J. J. Trujillo-Serrato, P. Joseph-Nathan, J. Org. Chem. 2001, 66, 1186-1192;
42. d) J. D. Sanchez, M. T. Ramos, C. Avendano, Tetrahedron Lett. 2000, 41, 2745-2748;
43. e) T. Kawasaki, R. Terashima, K. Sakaguchi, H. Sekiguchi, M. Sakamoto, Tetrahedron Lett. 1996, 37, 7525-7528;
44. f) D. Crich, A. B. Pavlovic, R. Samy, Tetrahedron 1995, 51, 6379-6384.
45. H. Harayama, T. Kuroki, M. Kimura, S. Tanaka, Y. Tamaru, Angew. Chem. Int. Ed. Engl. 1997, 36, 2352-2354.
46. M. Mori, M. Kimura, Y. Tamaru, manuscript to be published.
47. 3B is stable in water and alcohols, but undergoes hydrolysis slowly in contact with some 1,2- and 1,3-diols.
48. a) Y. Masuyama, in: Advances in Metal-Organic Chemistry; (Ed.: L. S. Liebeskind), JAI Press, 1994, vol. 3, p. 255;
49. b) Y. Tamaru, in Handbook of Organopalladium Chemistry for Organic Synthesis; (Ed.: E. Negishi), Wiley, New York, 2002, p. 1917.
50. M. Kimura, T. Tomizawa, Y. Horino, S. Tanaka, Y. Tamaru, Tetrahedron Lett. 2000, 41, 3627-3629.
51. Pd-catalyzed generation of allyl nucleophiles from allyl esters and ethers: a) Y. Tamaru, A. Tanaka, K. Yasui, S. Goto, S. Tanaka, Angew. Chem. Int. Ed. Engl. 1995, 34, 787-789;
52. b) Y. Tamaru, S. Goto, A. Tanaka, M. Shimizu, M. Kimura, Angew. Chem. Int. Ed. Engl. 1996, 35, 878-880;
53. c) M. Shimizu, M. Kimura, S. Tanaka, Y. Tamaru, Tetrahedron Lett. 1998, 39, 609-612;
54. d) M. Kimura, Y. Ogawa, M. Shimizu, M. Sueishi, S. Tanaka, Y. Tamaru, Tetrahedron Lett. 1998, 39, 6903-6906;
55. e) M. Kimura, I. Kiyama, T. Tomizawa, Y. Horino, S. Tanaka, Y. Tamaru, Tetrahedron Lett. 1999, 40, 6795-6798.
56. M. Kimura, M. Shimizu, K. Shibata, M. Tazoe, Y. Tamaru, Angew. Chem. Int. Ed. 2003, 42, 3392-3395.
57. M. Kimura, M. Shimizu, S. Tanaka, Y. Tamaru, Tetrahedron 2005, 61, 3709-3718.
58. M. Shimizu, M. Kimura, T. Watanabe, Y. Tamaru, Org. Lett. 2005, 7, 637-640.
59. a) S. Kumar, P. Kaur, Tetrahedron Lett. 2004, 45, 3413-3416;
60. b) I. Shibata, K. Nose, K. Sakamoto, M. Yasuda, A. Baba, J. Org. Chem. 2004, 69, 2185-2187;
61. c) R. Yanada, A. Kaieda, Y. Takemoto, J. Org. Chem. 2001, 66, 7516-7518;
62. d) I. R. Cooper, R. Grigg, W. S. MacLachlan, M. Thornton-Pett, V. Sridharan, Chem. Commun. 2002, 1372-1373.
63. S. Itsuno, K. Watanabe, K. Ito, K. A. A. El-Shehawy, A. A. Sarhan, Angew. Chem. Int. Ed. Engl. 1997, 36, 109-110.
64. R. Mukai, Y. Horino, S. Tanaka, Y. Tamaru, M. Kimura, J. Am. Chem. Soc. 2004, 126, 11138-11139.
65. a) B. M. Trost, M. L. Crawley, J. Am. Chem. Soc. 2002, 124, 9328-9329;
66. b) D. A. Singleton, B. E. Schulmeier, J. Am. Chem. Soc. 1999, 121, 9313-9317;
67. c) L. A. Paquette, D. R. Sauer, D. G. Gleary, M. A. Kinsella, C. M. Blackwell, L. G. An-derson, J. Am. Chem. Soc. 1992, 114, 7375-7387;
68. d) B. M. Trost, S. A. King, J. Am. Chem. Soc. 1990, 112, 408-422.
69. M. Shimizu, M. Kimura, T. Watanabe, Y. Tamaru, manuscript to be submitted.
70. B. M. Trost, G. A. Molander, J. Am. Chem. Soc. 1981, 103, 5969-5972.
71. M. Kimura, M. Sakaguchi, S. Tanaka, Y. Tamaru, manuscript to be submitted.
72. C.-H. Jun, Chem. Soc. Rev. 2004, 33, 610-618.