A new preparative method for allylic indium(III) reagents by reductive transmetalation of π-allylpalladium(II) with indium(I) salts

Organic Letters

Volumn 2, Issue 6, 2000, Pages 847-849

  Araki, Shuki ^a   Kamei, Toshiya ^a   Hirashita, Tsunehisa ^a   Yamamura, Hatsuo ^a   Kawai, Masao ^a  

^a NAGOYA INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000724545     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol005610i     Document Type: Article

References (22)

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3. For recent papers, see: (c) Hirashita, T.; Kamei, T.; Horie, T.; Yamamura, H.; Kawai, M.; Araki, S. J. Org. Chem. 1999, 64, 172-177.
4. (d) Araki, S.; Kamei, T.; Igarashi, Y.; Hirashita, T.; Yamamura, H.; Kawai, M. Tetrahedron Lett. 1999, 40, 7999-8002.
5. (e) Klaps, E.; Schmid, W. J. Org. Chem. 1999, 64, 7537-7546 and references therein.
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8. (c) Li, C.-J.; Chan, T.-H. Tetrahedron 1999, 55, 11149-11176.
9. (d) Paquette, L. A. In Green Chemistry: Frontiers in Benign Chemical Synthesis and Processing; Anastas, P., Williamson, T., Eds.; Oxford University Press: New York, 1998.
10. For example, see: Araki, S.; Hone, T.; Kato, M.; Hirashita, T.; Yamamura, H.; Kawai, M. Tetrahedron Lett. 1999, 40, 2331-2334.
11. Transmetalation of allylstannane with indium(III) chloride also gives allylindium(III): Marshall, J. A.; Hinkle, K. W. J. Org. Chem. 1995, 60, 1920-1921. Li, X.-R.; Loh, T.-P. Tetrahedron: Asymmetry 1996, 7, 1535- 1538.
12. Transmetalation of allylstannane with indium(III) chloride also gives allylindium(III): Marshall, J. A.; Hinkle, K. W. J. Org. Chem. 1995, 60, 1920-1921. Li, X.-R.; Loh, T.-P. Tetrahedron: Asymmetry 1996, 7, 1535-1538.
13. Araki, S.; Ito, H.; Butsugan, Y. J. Org. Chem. 1988, 55, 1831-1833. Araki, S.; Shimizu, T.; Johar, P. S.; Jin, S.-J.; Butsugan, Y. J. Org. Chem. 1991, 56, 2538-2542.
14. Araki, S.; Ito, H.; Butsugan, Y. J. Org. Chem. 1988, 55, 1831-1833. Araki, S.; Shimizu, T.; Johar, P. S.; Jin, S.-J.; Butsugan, Y. J. Org. Chem. 1991, 56, 2538-2542.
15. Araki, S.; Ito, H.; Katsumura, N.; Butsugan, Y. J. Organomet. Chem. 1989, 369, 291-296.
16. Allylic chlorides and phosphates are usable only in the presence of iodide salts such as sodium iodide via the in situ conversion to allylic iodides (see ref 5).
17. Recently, Chan reported a new preparation of allylindium(I) via a transmetalation of allylmercury with metallic indium in water concerning the structural study of the allylindium reagents prepared in aqueous media: Chan, T.-H.; Yang, Y. J. Am. Chem. Soc. 1999, 121, 3228-3229.
18. A pathway involving transient Pd-In complexes as intermediates has been suggested for the formation of allenylindium reagents from propargylic mesylates by Pd-catalyzed metalation with InI: Marshall, J. A.; Grant, C. M. J. Org. Chem. 1999, 64, 696-697. See also: Perez, I.; Sestelo, J. P.; Sarandeses, L. A. Org. Lett. 1999, 1. 1267-1269.
19. A pathway involving transient Pd-In complexes as intermediates has been suggested for the formation of allenylindium reagents from propargylic mesylates by Pd-catalyzed metalation with InI: Marshall, J. A.; Grant, C. M. J. Org. Chem. 1999, 64, 696-697. See also: Perez, I.; Sestelo, J. P.; Sarandeses, L. A. Org. Lett. 1999, 1. 1267-1269.
20. For example, see: Tamaru, Y. J. Organomet. Chcm. 1999, 576, 215-231. See also: Kimura, M.; Kiyama, I.; Tomizawa, T.; Horino, Y.; Tanaka, S.; Tamara, Y. Tetrahedron Lett. 1999, 40, 6795-6798 and references therein.
21. For example, see: Tamaru, Y. J. Organomet. Chcm. 1999, 576, 215-231. See also: Kimura, M.; Kiyama, I.; Tomizawa, T.; Horino, Y.; Tanaka, S.; Tamara, Y. Tetrahedron Lett. 1999, 40, 6795-6798 and references therein.
22. 2/hexane = 1/1) to give l-phenyl-3-buten-l-ol (64 mg, 86% yield).