Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 36, 2006 - Issue 17
61
Views
5
CrossRef citations to date
0
Altmetric
Original Articles

Studies on the Allylation Reactions of Aldehydes and Ketones with Lanthanum in Water

, , &
Pages 2475-2481 | Received 12 Dec 2005, Published online: 27 Oct 2006

References

  • Wakefield , B. J. 1995 . Organomagnesium Methods in Organic Synthesis , Best Synthetic Methods series Edited by: Katritzky , A. R. , Meth‐Cohn , O. and Rees , C. W. San Diego : Academic Press .
  • Zhou , C. L. , Zha , Z. G. , Wang , Z. Y. and Wu , J. H. 2002 . Simple and clean synthesis: Tin‐mediated allylation of carbonyl compound in water . Chin. J. Chem. , 20 : 718 – 721 .
  • Chan , T. H. , Yang , Y. and Li , C. J. 1999 . Organometallic reactions in aqueous media: The nature of the organotin intermediate in the tin‐mediated allylation of carbonyl compounds . J. Org. Chem. , 64 : 4452 – 4455 .
  • Loh , T. P. and Xu , J. 1999 . Trifluoromethane sulphonic acid: A Bronsted acid catalyst for the addition of allyltributylstannanes to carbonyl compounds in water . Tetrahedron Lett. , 40 : 2431 – 2434 .
  • Zha , Z. G. , Wang , Y. S. , Yang , G. and Zhang , L. 2002 . Efficient Barbier reaction of carbonyl compounds improved by a phase transfer in water . Green Chem. , 4 : 578 – 580 .
  • Wang , Z. Y. , Zha , Z. G. and Zhou , C. L. 2002 . Application of tin and nanometer tin in allylation of carbonyl compounds in tap water . Org. Lett. , 4 ( 10 ) : 1683 – 1685 .
  • Chung , W. J. , Higashiya , S. , Oba , Y. and Welch , J. T. 2003 . Indium‐ and zinc‐mediated allylation of difluoroacetyltrialkylsilanes in aqueous media . Tetrahedron , 59 : 10031 – 10036 .
  • Basu , M. K. and Banik , B. K. 2001 . Samarium‐mediated barbier reaction of carbonyl compounds . Tetrahedron Lett. , 42 : 187 – 189 .
  • Wang , Z. Y. , Yuan , S. Z. and Li , C. J. 2002 . Gallium‐mediated of carbonyl compounds in water . Tetrahedron Lett. , 43 : 5097 – 5099 .
  • Su , W. K. , Zhang , Y. M. and Li , Y. S. 2001 . Allylation of diselenides, aldehydes and ketones with ytterbium/allyl bromide system . Chin. J. Chem. , 19 ( 4 ) : 381 – 385 .
  • Li , C. J. , Meng , Y. and Yi , X. H. 1997 . Manganese‐mediated reactions in aqueous media: Chemoselective allylation and pinacol coupling of aryl aldehydes . J. Org. Chem. , 62 : 8632 – 8633 .
  • Zhang , W. C. and Li , C. J. 1999 . Magnesium‐mediated carbon–carbon bond formation in aqueous media: Barbier–Grignard allylation and pinacol coupling of aldehydes . J. Org. Chem. , 64 : 3230 – 3236 .
  • Lothar , W. B. , Storch , E. C. , Malvestiti , I. and Silva , M. F. D. 1998 . Silver‐catalyzed zinc Barbier reaction of benzylic halides in water . Tedrahedron Lett. , 39 : 9393 – 9396 .
  • Chan , T. H. and Li , C. J. 1990 . Organometallic reactions in aqueous medium: Conversion of carbonyl compounds to 1,3‐butadienes or vinyloxiranes . Organometallics , 9 : 2649 – 2650 .
  • Marton , D. , Stivanello , D. and Tagliavini , G. 1996 . 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 : 2731 – 2737 .
  • Wilson , S. R. and Guazzaroni , M. E. 1989 . Synthesis of homoallylic alcohols in aqueous media . J. Org. Chem. , 54 : 3087 – 3091 .
  • Lee , A. S. Y. , Chu , S. F. , Chang , Y. T. and Wang , S. H. 2004 . Synthesis of homopropargyl alcohols via sonochemical Barbier‐type reaction . Tetrahedron Lett. , 45 : 1551 – 1553 .
  • Estevam , I. H. S. and Bieber , L. W. 2003 . Barbier‐type allylation of iminium ions generated in situ in aqueous medium . Tetrahedron Lett. , 44 : 667 – 670 .
  • Bian , Y. J. , Li , J. T. and Li , T. S. 2002 . Applications of ultrasound in organic synthesis using metal reagent . Chin. J. Org. Chem. , 22 ( 4 ) : 227 – 232 .
  • Li , J. T. , Bian , Y. J. , Zang , H. J. and Li , T. S. 2002 . Pinacol coupling of aromatic aldehydes and ketones using magnesium in aqueous ammonium chloride under ultrasound . Synth. Commun. , 32 : 547 – 551 .
  • Bian , Y. J. , Liu , S. M. , Li , J. T. and Li , T. S. 2002 . Pinacol coupling of aromatic aldehydes and ketones using aluminum under ultrasound . Synth. Commun. , 32 : 1169 – 1174 .
  • Li , J. T. , Bian , Y. J. , Liu , S. M. and Li , T. S. 2003 . Reductive coupling of aromatic aldehydes using manganese under ultrasound irradiation . Chin. J. Org. Chem. , 23 : 479 – 482 .
  • Bian , Y. J. , Zhao , Y. J. , Li , M. X. and Li , J. T. 2004 . Reductive coupling of aromatic aldehydes using manganese under ultrasound irradiation . Chin. J. Org. Chem. , 24 ( 7 ) : 828 – 830 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.