The allylation reactions of aromatic aldehydes and ketones with tin dichloride in water

Ultrasonics Sonochemistry

Volumn 17, Issue 1, 2010, Pages 58-60

  Bian, Yan Jiang ^a   Xue, Wei Li ^a   Yu, Xu Guang ^b  

^a LANGFANG NORMAL UNIVERSITY   (China)

^b BEIJING GENERAL RESEARCH INSTITUTE OF MINING AND METALLURGY   (China)

Author keywords

Allylation; Tin dichloride; Ultrasound irradiation; Water

Indexed keywords

ALDEHYDES; ALLYLATION; AROMATIC COMPOUNDS; CHLORINE COMPOUNDS; IRRADIATION; KETONES; WATER;

ALLYLATION REACTIONS; AROMATIC ALDEHYDE; HOMOALLYL ALCOHOL; ULTRASOUND IRRADIATION;

TIN COMPOUNDS;

ALCOHOL DERIVATIVE; ALDEHYDE DERIVATIVE; ALLYL COMPOUND; KETONE DERIVATIVE; STANNOUS CHLORIDE; WATER;

ALLYLATION; ARTICLE; INTERMETHOD COMPARISON; PRIORITY JOURNAL; QUANTUM YIELD; REACTION ANALYSIS; REACTION TIME; ULTRASOUND;

ALDEHYDES; HYDROCARBONS, AROMATIC; KETONES; MICROFLUIDICS; RADIATION DOSAGE; SONICATION; TIN COMPOUNDS; WATER;

EID: 70249086549     PISSN: 13504177     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ultsonch.2009.05.008     Document Type: Article

References (24)

1. B.J. Wakefield, in: A.R. Katritzky, O. Meth-Cohn, C.W. Rees (Eds.), Organomagnesium Methods in Organic Synthesis, Best Synthetic Methods Series, Academic Press, San Diego, 1995.
2. Zhou C.L., Zha Z.G., Wang Z.Y., and Wu J.H. Simple and clean synthesis: tin-mediated allylation of carbonyl compound in water. Chin. J. Chem. 20 (2002) 718-721
3. Chan T.H., Yang Y., and Li C.J. Organometallic reactions in aqueous media. The nature of the organotin intermediate in the tin-mediated allylation of carbonyl compounds. J. Org. Chem. 64 (1999) 4452-4455
4. Loh T.P., and Xu J. Trifluoromethane sulphonic acid: a bronsted acid catalyst for the addition of allyltributylstannanes to carbonyl compounds in water. Tetrahedron Lett. 40 (1999) 2431-2434
5. Zha Z.G., Wang Y.S., Yang G., Zhang, and Li. Efficient Barbier reaction of carbonyl compounds improved by a phase transfer in water. Green Chem. 4 (2002) 578-580
6. Wang Z.Y., Zha Z.G., and Zhou C.L. Application of tin and nanometer tin in allylation of carbonyl compounds in tap water. Org. Lett. 4 10 (2002) 1683-1685
7. Chung W.J., Higashiya S., Oba Y., and Welch J.T. Indium- and zinc-mediated allylation of difluoroacetyltrialkylsilanes in aqueous media. Tetrahedron 59 (2003) 10031-10036
8. Basu M.K., and Banik B.K. Samarium-mediated Barbier reaction of carbonyl compounds. Tetrahedron Lett. 42 (2001) 187-189
9. Wang Z.Y., Yuan S.Z., and Li C.J. Gallium-mediated of carbonyl compounds in water. Tetrahedron Lett. 43 (2002) 5097-5099
10. Su W.K., Zhang Y.M., and Li Y.S. Allylation of diselenides, aldehydes and ketones with ytterbium/allyl bromide system. Chin. J. Chem. 19 4 (2001) 381-385
11. Li C.J., Meng Y., and Yi X.H. Manganese-mediated reactions in aqueous media: chemoselective allylation and pinacol coupling of aryl aldehydes. J. Org. Chem. 62 (1997) 8632-8633
12. Zhang W.C., and Li C.J. Magnesium-mediated carbon-carbon bond formation in aqueous media: Barbier-Grignard allylation and pinacol coupling of aldehydes. J. Org. Chem. 64 (1999) 3230-3236
13. Lothar W.B., Storch E.C., Malvestiti I., and Silva M.F.D. Silver catalyzed zinc Barbier reaction of benzylic halides in water. Tedrahedron Lett. 39 (1998) 9393-9396
14. Chan T.H., and Li C.J. Organometallic reactions in aqueous medium conversion of carbonyl compounds to 1,3-butadienes or vinyloxiranes. Organometallics 9 (1990) 2649-2650
15. Marton D., Stivanello D., and Tagliavini G. Stereochemical study of the allylation of aldehydes with allyl halides in cosolvent/water (salt)/Zn and in cosolvent/water (salt)/Zn/haloorganotin media. J. Org. Chem. 61 (1996) 2731-2737
16. S.R. Wilson, M.E. Guazzaroni, Synthesis of homoallylic alcohols in aqueous media, J. Org. Chem. 54 (1989) 3087-3091
17. Lee A.S.Y., Chu S.F., Chang Y.T., and Wang S.H. Synthesis of homopropargyl alcohols via sonochemical Barbier-type reaction. Tetrahedron Lett. 45 (2004) 1551-1553
18. Estevam I.H.S., and Bieber L.W. Barbier-type allylation of iminium ions generated in situ in aqueous medium. Tetrahedron Lett. 44 (2003) 667-670
19. Bian Y.J., Li J.T., and Li T.S. Applications of ultrasound in organic synthesis using metal reagent. Chin. J. Org. Chem. 22 4 (2002) 227-232
20. Y.J. Bian, C.R. Fan, X.H. Hu, J.T. Li, Zinc-mediated allylation reactions of aldehydes and ketones in aqueous media under ultrasonic irradiation, Indian J. Chem. B 45 (6) (2006) 1587-1589.
21. Y.J. Bian, J.P. Xia, J.Q. Zhang, The allylation reactions of aromatic aldehydes and ketones with tin in water under ultrasound irradiation, Chin. J. Org. Chem. 26 (12) (2006) 1696-1699.
22. Bian Y.J., Zhang J.Q., Xia J.P., and Li J.T. Studies on the allylation reactions of aldehydes and ketones with lanthanum in water. Synth. Commun. 36 17 (2006) 2475-2481
23. Bian Y.J., and Wang H. Studies on the allylation reactions of aromatic aldehydes with neodymium in water. Chin. J. Org. Chem. 27 120 (2007) 1582-1585
24. Bian Y.J., Zhang J.Y., and Li J.T. Allylation reactions of aromatic aldehydes and ketones with lithium in THF under ultrasonic irradiation. J. Chem. Res. (2007) 162-164