Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2009 - Issue 19
233
Views
7
CrossRef citations to date
0
Altmetric
Original Articles

Mild and Efficient Deoxygenation of Amine-N-oxides with BiCl3/Indium System

&
Pages 3550-3554 | Received 18 Nov 2008, Published online: 04 Sep 2009

REFERENCES

  • Ochiai , E. In Aromatic Amine Oxides ; Elsevier : Amsterdam , 1967 ; pp. 184 – 209 .
  • (a) Malinoswaki , M. Titanium(0) reagents, 1: A facile deoxygenation of unfunctionalized aromatic N-oxides . Synthesis 1987 , 732 ; (b) Balicki , R. TiCl4/NaI—A novel, efficient reagent for mild reduction of the N-O bond in amine N-oxides and nitrones . Chem. Ber. 1990 , 647 ; (c) Balicki , R. ; Kaczmarek , L. ; Malinnowski , M. Selective reduction of the N-O bond in heteroaromatic N-oxides by TiCl4/SnCl2 . Synth. Commun. 1989 , 19 , 897 .
  • Balicki , R. ; Cybulski , M. ; Maciejewski , G. An efficient deoxygenation of heteroaromatic N-oxides using zinc dust/ammonium formate reagent system . Synth. Commun. 2003 , 33 , 4137 .
  • Ilias , M. H. ; Barman , D. C. ; Prajapati , D. ; Sandhu , J. S. An indium-mediated efficient chemoselective deoxygenation of N-oxides and nitrons . Tetrahedron Lett. 2002 , 43 , 1877 .
  • Jousseaume , B. ; Chanson , E. Mild selective deoxygenation of amine oxides by tin–tin bonded derivatives . Synthesis 1987 , 55 .
  • Balicki , R. Efficient deoxygenation of heteroaromatic N-oxides with ammonium formate as a catalytic hydrogen transfer agent . Synthesis 1989 , 645 .
  • Zhang , Y. ; Lin , R. Some deoxygenation and reduction reactions with samarium diiodide . Synth. Commun. 1987 , 17 , 329 .
  • Ilankumaran , P. ; Chandrasekara , S. Chemoselective deoxygenation of nitrones and N-oxides with tetrathiomolybdate . Tetrahedron Lett. 1995 , 36 , 4881 .
  • Yadav , J. S. ; Subba Reddy , B. V. ; Muralidhar Reddy , M. Indium-mediated deoxygenation of amine-N-oxides in aqueous media. Tetrahedron Lett. 2000, 41, 2663.
  • Yoo , B. W. ; Choi , J. W. ; Yoon , C. M. A facile and efficient deoxygenation of amine-N-oxides with Mo(CO)6 . Tetrahedron Lett. 2006 , 47 , 125 .
  • (a) Genliang , L. ; Yongmin , Z. A novel synthesis of benzyl sulfides and selenides via Sm/BiCl3 system in aqueous media . Synth. Commun. 1998 , 28 , 4479 ; (b) Norikazu , M. ; Mami , N. ; Shunsuke , M. ; Tomohiro , F. ; Mokoto , W. A convenient one-pot allylation of aldehydes with allylic halides prepared in situ from allylic alcohols in the presence of metallic bismuth . Bull. Chem. Soc. Jpn. 2000 , 73 , 689 ; (c) Makoto , W. ; Tomohiro , F. ; Mika , M. ; Toshikazu , T. ; Norikazu , M. A novel aqueous Barbier–Grignard-type allylation of aldehydes in a Mg/BiCl3 bimetal system . Tetrahedron Lett. 1997 , 38 , 8045 ; (d) Zhen , S. ; Jinqi , Z. ; Huixian , Z. ; Minmin , Y. A novel one-pot Reformatsky type reaction via bismuth salt in aqueous media . Tetrahedron Lett. 1997 , 38 , 2733 .
  • (a) Choi , K. H. ; Choi , K. I. ; Kim , J. H. ; Yoon , C. M. ; Yoo , B. W. Mild and efficient deoxygenation of epoxides with bis(cyclopentadienyl)titanium(IV) dichloride–indium system . Bull. Korean Chem. Soc. 2005 , 26 , 1495 ; (b) Han , J. H. ; Choi , J. W. ; Choi , K. I. ; Kim , J. H. ; Kim , J. H. ; Yoon , C. M. ; Yoo , B. W. A facile deoxygenation of amine-N-oxide with NiCl2·6H2O/indium system . Bull. Korean Chem. Soc. 2005 , 26 , 1921 ; (c) Han , J. H. ; Choi , J. W. ; Choi , K. I. ; Kim , J. H. ; Yoo , B. W. A facile and efficient reduction of nitroarenes with NiCl2·6H2O/indium system . Bull. Korean Chem. Soc. 2006 , 27 , 1115 ; (d) Han , J. H. ; Choi , K. I. ; Kim , J. H. ; Yoon , C. M. ; Yoo , B. W. Facile deoxygenation of amine-N-oxide with CoCl2·6H2O–indium system . Synth. Commun. 2006 , 36 , 415 .

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.