Palladium-Catalyzed Allylation of Carbonyl Compounds with Various Allylic Compounds Using In-InCl3 in Aqueous Media

Taeg-Su Jang; Gyochang Keum; Soon Bang Kang; Bong Young Chung; Youseung Kim

doi:10.1055/s-2003-38059

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Synthesis 2003(5): 0775-0779
DOI: 10.1055/s-2003-38059

SPECIALTOPIC

Palladium-Catalyzed Allylation of Carbonyl Compounds with Various Allylic Compounds Using In-InCl₃ in Aqueous Media

Taeg-Su Jang^a, Gyochang Keum^a, Soon Bang Kang^a, Bong Young Chung^b, Youseung Kim*^a
^a Biochemicals Research Center, Korea Institute of Science and Technology, Cheongryang P. O. Box 131, Seoul 130-650, Korea
Fax: +82(2)9585189; e-Mail: yosekim@kist.re.kr;
^b Department of Chemistry, Korea University, Seoul 136-701, Korea

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Publication History

Received 15 February 2003
Publication Date:
21 March 2003 (online)

Abstract
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Abstract

Various allylic compounds can be effectively applied to palladium-catalyzed allylation of carbonyl compounds via the formation of π-allylpalladium(II) intermediates and their transmetalation with indium in the presence of indium trichloride in aqueous media.

Key words

allylation - palladium - indium - indium trichloride - aqueous

References

1a Li C.-J. Chan T.-H. In Organic Reactions in Aqueous Media John Wiley & Sons; New York: 1997.

Crossref Google Scholar
1b Hashami ASK. J. Prakt. Chem. 1998, 340: 84-89

Crossref Google Scholar
2a Cintas P. Synlett 1995, 1087

Crossref Google Scholar
2b Li C.-J. Chan T.-H. Tetrahedron 1999, 55: 11149

Crossref Google Scholar
3 Yoo J. Oh KE. Keum G. Kang SB. Kim Y. Polyhedron 2000, 19: 549

Crossref Google Scholar
4a Lim HJ. Keum G. Kang SB. Chung BY. Kim Y. Tetrahedron Lett. 1998, 39: 4367

Google Scholar
4b Lim HJ. Keum G. Kang SB. Chung BY. Kim Y. Tetrahedron Lett. 1999, 4: 1547

Google Scholar
5 Marshall JA. Chem. Rev. 2000, 10: 3163

Google Scholar
6a Marshall JA. Grant CM. J. Org. Chem. 1999, 64: 696

Google Scholar
6b Araki S. Kamei T. Hirashita T. Yamamura H. Kawai M. Org. Lett. 2000, 2: 847

Google Scholar
6c Anwar U. Grigg R. Rasparini M. Savic V. Sridharan V. Chem. Commun. 2000, 645

Google Scholar
6d Anwar U. Grigg R. Sridharan V. Chem. Commun. 2000, 933

Google Scholar
6e Takemoto Y. Anzai M. Yanada R. Fujii N. Ohno H. Ibuka T. Tetrahedron Lett. 2001, 4: 1725

Google Scholar
6f Araki S. Kameda K. Tanaka J. Hirashita T. Yamamura H. Kawai M. J. Org. Chem. 2001, 6: 7919

Google Scholar
7 Dean JA. In Lange’s Handbook of Chemistry 14th ed., Chap. 8: McGraw-Hill Inc.; New York: 1992. p.124

Google Scholar
8 Kang S. Jang T.-S. Keum G. Kang SB. Han S.-Y. Kim Y. Org. Lett. 2000, 2: 3615

Crossref Google Scholar
9 Bergbreiter DE. Weatherford DA. J. Chem. Soc., Chem. Commun. 1989, 883

Crossref Google Scholar
10 Takahara JP. Masuyama Y. Kurusu Y. J. Am. Chem. Soc. 1992, 11: 2577

Google Scholar
11a Atkins KE. Walker WE. Manyik RM. Tetrahedron Lett. 1970, 3821

Google Scholar
11b Lumin S. Falck JR. Capdevila J. Karara A. Tetrahedron Lett. 1992, 3: 2091

Google Scholar
12 Stary I. Stara IG. Kocovsky P. Tetrahedron Lett. 1993, 34: 179

Crossref Google Scholar
13 Yang SC. Hung CW. J. Org. Chem. 1999, 6: 5000

Google Scholar
14 Chan T.-H. Yang Y. J. Am. Chem. Soc. 1999, 1: 3228

Google Scholar