Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 38, 2008 - Issue 10
430
Views
8
CrossRef citations to date
0
Altmetric
Original Articles

Direct Oxidation of N‐Benzylamides to Aldehydes or Ketones by N‐Bromosuccinimide

, , &
Pages 1629-1637 | Received 21 Sep 2007, Published online: 24 Apr 2008

References

  • Katritzky , A. R. T. and Taylor , R. J. K. 2005 . Comprehensive Organic Functional Group Transformations , 1st edn. Amsterdam, , Netherlands : Elsevier .
  • Ishihara , K. Y.T. 2004 . Synthesis of carboxamides by LDA‐catalyzed Haller–Bauer and Cannizzaro reactions . Org. Lett. , 6 : 1983 – 1986 .
  • Nemchik , A. , Badescu , V. and Phanstiel , O. 2003 . N‐(Benzoyloxy)amines: An investigation of their thermal stability, synthesis, and incorporation into novel peptide constructs . Tetrahedron , 59 : 4315 – 4325 .
  • Padmanabhan , S. L. , Thakkar , R. C. , Paresh , M. and Durant , G. J. 2001 . A general procedure for the synthesis of acylguanidines derived from aliphatic and aromatic amines . Synth. Commun. , 3 : 2491 – 2497 .
  • Newman , M. S. C. and Edward , G. 1958 . Effect of surfaces on the McFadyen–Stevens aldehyde synthesis: An improved procedure . J. Am. Chem. Soc. , 80 : 862 – 864 .
  • Doyle , M. P. D. , Donnelly , D. J. , Kooistra , S. J. , Odubela , D. A. , Abayomi , A. , West , C. T. and Zonnebelt , S. M. 1974 . Silane reductions in acidic media, III: Reductions of aldehydes and ketones to alcohols and alcohol derivatives: General syntheses of alcohols, symmetrical ethers, carboxylate esters and acetamides . J. Org. Chem. , 39 : 2740 – 2747 .
  • Minisci , F. P. C. , Recupero , F. , Fontana , F. and Pedulli , G. F. 2002 . Aerobic oxidation of N‐alkylamides catalyzed by N‐hydroxyphthalimide under mild conditions: Polar and ethalpic effects . J. Org. Chem. , 67 : 2671 – 2676 .
  • Miura , K. , Ootsuka , K. , Suda , S. , Nishikori , H. and Hosomi , A. 2001 . Lewis acid–catalyzed reductive amination of carbonyl compounds with aminohydrosilanes . Synlett. , : 1617 – 1619 .
  • Pan , S. C. and List , B . 2007 . Catalytic one‐pot, three‐component Acyl–Strecker reaction . Synlett. , : 318 – 320 .
  • Brown , E. G. N. and John , M. 1997 . Alkylation of Rink's amide linker on polystyrene resin: A reductive amination approach to modified amine‐linkers for the solid phase synthesis of N‐substituted amide derivatives . Tetrahedron Lett. , 38 : 8457 – 8460 .
  • Dube , D. S. and Andrew , A. 1999 . Reductive N‐alkylation of amides, carbamates and ureas . Tetrahedron Lett. , 40 : 2295 – 2298 .
  • Elmorsy , S. S. B. , Doria , S. , Nour , M. A. and Kandeel , E. M. 1994 . The direct synthesis of secondary amides from aldehydes: A novel general redox procedure mediated by iodotrichlorosilane (ITCS) . Zeitschrift fuer Naturforschung, B: Chem. Sci. , 49 : 417 – 421 .
  • Hans‐René Bjørsvik , F. F. , Liguoric , L. A. and Minisci , F. 2001 . A bromine‐catalysed free‐radical oxidation of acetamides from primary and secondary alkylamines by H2O2 . Chem. Commun. , 6 : 523 – 524 .
  • Jaisankar , P. P. , Bikash , G. and Venkatachalam , S. 2002 . Microwave assisted McFadyen–Stevens and Huang–Minlon reactions . Synth. Commun. , 32 : 2569 – 2573 .
  • Thomas , C. W. L. and Routley , H. A. 1988 . Thermolysis of benzhydrazones in the presence of copper . Tetrahedron Lett. , 29 : 811 – 812 .
  • Wang , J.‐R. , Lei , L. , Wang , Y.‐F. , Zhang , Y. , Deng , W. and Guo , Q.‐X. 2005 . Aerobic oxidation with N‐hydroxyphthalimide catalysts in ionic liquid . Tetrahedron Lett. , 46 : 4647 – 4651 .
  • Gopinathan , M. B. and Vivekananda , B. M. 1979 . A new general method for the introduction of the aldehyde function in aromatic compounds . Tehtrahedron Lett. , 20 : 3875 – 3876 .
  • Kuang , L. P. , Zhou , J. , Chen , S. and Ding , K. 2007 . Room‐temperature debenzylation of N‐benzylcarboxamides by N‐bromosuccinimide . Synthesis , 20 : 3129 – 3134 .

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.