Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 37, 2007 - Issue 9
767
Views
16
CrossRef citations to date
0
Altmetric
Original Articles

N‐Bromosuccinimide: A Facile Reagent for the Oxidation of Benzylic Alcohols to Aldehydes

&
Pages 1571-1577 | Received 29 Sep 2006, Published online: 11 May 2007

References

  • Larock , R. C. 1999 . Comprensive Organic Transformations New York : Wiley .
  • Brink , G. J. T. , Andrews , I. W. C. E. and Sheldon , R. A. 2000 . Green, catalytic oxidation of alcohols in water . Science , 287 : 1636 – 1639 .
  • Barrett , A. G. M. , Braddock , D. C. , McKinnell , R. M. and Waller , F. J. 1999 . Ytterbium(III) triflate as a recyclable catalyst for the selective atom economic oxidation of benzyl alcohols to benzaldehydes . Synlett , : 1489 – 1490 .
  • Sato , K. , Takagi , J. , Aoki , M. and Noyori , R. 1998 . Hydrogen peroxide oxidation of benzylic alcohols to benzaldehydes and benzoic acids under halide‐free conditions . Tetrahedron Lett. , 39 : 7549 – 7552 .
  • Barhate , N. B. , Sasidharan , M. , Sudalai , A. and Wakharkar , R. D. 1996 . Selective catalytic oxidation of benzylic alcohols to the corresponding carbonyl compounds with TBHP over CrS‐2 . Tetrahedron Lett. , 37 : 2067 – 2070 .
  • Singh , R. P. , Subbarao , H. N. and Suk , D. 1979 . Organic reactions in a solid matrix—V: Silica‐gel supported chromic acid reagents . Tetrahedron , 35 : 1789 – 1793 .
  • Ley , S. V. , Madin , A. , Trost , B. M. and Flemming , I. 1991 . Comprensive Organic Synthesis Vol. 7 , 305 – 327 . Oxford : Pergamon Press .
  • Collons , J. C. , Hess , W. W. and Franck , F. J. 1968 . Dipyridine‐chromium(VI) oxide oxidation of alcohols in dichloromethane . Tetrahedron Lett. , 9 : 3363 – 3366 .
  • Corey , E. J. and Fleet , G. W. J. 1973 . Chromium trioxide‐3,5‐dimethylpyrazole complex as a reagent for oxidation of alcohols to carbonyl compounds . Tetrahedron Lett. , 14 : 4499 – 4501 .
  • Corey , E. J. and Suggs , J. W. 1975 . Pyridinium chlorochromate: An efficient reagent for oxidation of primary and secondary alcohols to carbonyl compounds . Tetrahedron Lett. , 16 : 2647 – 4650 .
  • Corey , E. J. and Schmith , G. 1979 . Useful procedures for the oxidation of alcohols involving pyridinium dichromate in approtic media . Tetrahedron Lett. , 20 : 399 – 402 .
  • Guziec , F. S. and Luzzio , F. A. 1980 . The oxidation of alcohols using 2,2′‐bipyridinium chlorochromate . Synthesis , : 691 – 693 .
  • Bhattacharjee , M. N. , Chaudhuri , M. K. and Purkayastha , S. 1987 . Some aspects of pyridinium fluorochromate, C5H5NhCrO3F (PFC), oxidations: Stoichiometry of oxidation of alcohols, evidence for oxygen transfer, and the identity of the reduced chromium species . Tetrahedron , 43 : 5389 – 5392 .
  • Murugasan , V. and Pandurangan , A. 1992 . Quinolinium fluorochromate—A new reagent for the oxidation of organic compounds . Indian J. Chem. Sec. B , 31B : 377 – 378 .
  • Srinivasan , R. , Ramesh , C. V. , Madhulatha , W. and Balasubramanian , K. 1996 . Oxidation of alcohols by quinolinium chlorochromate . Indian J. Chem. Sec. B , 35B : 480 – 481 .
  • Tajbakhsh , M. , Hosseinzadeh , R. and Niaki , Y. M. 2002 . Synthesis and application of 2,6‐dicarboxypyridinium chlorochromate as a new oxidizing reagent for alcohols, silyl ethers, and THP ethers under mild and non‐aqueous conditions . J. Chem. Res. Synop. , : 508 – 510 .
  • Schultz , H. S. , Freyermuth , H. B. and Buc , S. R. 1963 . New catalysts for the oxidation of sulfides to sulfones with hydrogen peroxide . J. Org. Chem. , 28 : 1140 – 1142 .
  • Ishi , Y. , Tanaka , H. and Nishiyama , Y. 1994 . Selectivity in oxidation of sulfides with hydrogen peroxide by [π‐C5H5N+(CH2)15CH3]3PM12O40 3− and [π‐C5H5N+(CH2)15CH3]3{PO4[M(O)(O2)2]4}3− (M=Mo or W) . Chem. Lett. , 23 : 1 – 4 .
  • Gresley , N. M. , Griffith , W. P. , Laemmel , A. C. , Nogueira , H. I. S. and Parkin , B. C. 1997 . Studies on polyoxo‐ and polyperoxo‐metalates part 5: Peroxide‐catalysed oxidations with heteropolyperoxo‐tungstates and ‐molybdates . J. Mol. Catal. A: Chem. , 117 : 185 – 198 .
  • Sato , K. , Hyodo , M. , Aoki , M. , Zheng , X. Q. and Noyori , R. 2001 . Oxidation of sulfides to sulfoxides and sulfones with 30% hydrogen peroxide under organic solvent‐ and halogen‐free conditions . Tetrahedron , 57 : 2469 – 2476 .
  • Kaneda , K. , Fuji , M. and Morioka , K. 1996 . Highly selective oxidation of allylic alcohols to α,β‐unsaturated aldehydes using Pd cluster catalysts in the presence of molecular oxygen . J. Org. Chem. , 61 : 4502 – 4505 .
  • Peterson , K. P. and Larock , R. C. 1998 . Palladium‐catalyzed oxidation of primary and secondary allylic and benzylic alcohols . J. Org. Chem. , 63 : 3185 – 3189 .
  • Kaneda , K. , Yamashita , T. , Matsushita , T. and Ebitani , K. 1998 . Heterogeneous oxidation of allylic and benzylic alcohols catalyzed by Ru‐Al‐Mg hydrotalcites in the presence of molecular oxygen . J. Org. Chem. , 63 : 1750 – 1751 .
  • Yamaguchi , K. , Mori , K. , Mizugaki , T. , Ebitani , K. and Kaneda , K. 2000 . Creation of a monomeric Ru species on the surface of hydroxyapatite as an efficient heterogeneous catalyst for aerobic alcohol oxidation . J. Am. Chem. Soc. , 122 : 7144 – 7145 .
  • Chaudhuri , P. , Hess , M. , Muller , J. , Hildenbrand , K. , Bill , E. and Weyhermller , T. K. 1999 . Aerobic oxidation of primary alcohols (including methanol) by copper(II)‐ and zinc(II)‐phenoxyl radical catalysts . J. Am. Chem. Soc. , 121 : 9599 – 9600 .
  • Pagliaro , M. and Ciriminna , R. 2001 . New recyclable catalysts for aerobic alcohols oxidation: Sol‐gel ormosils doped with TPAP . Tetrahedron Lett. , 42 : 4511 – 4514 .
  • Sharma , V. B. , Jain , S. L. and Sain , B. 2003 . Cobalt phthalocyanine catalyzed aerobic oxidation of secondary alcohols: An efficient and simple synthesis of ketones . Tetrahedron Lett. , 44 : 383 – 386 .
  • Narasimha Moorthy , J. , Singhal , N. and Ventakrishnan , P. 2004 . Studies on oxidations with IBX: Oxidation of alcohols to aldehydes under solvent‐free conditions . Tetrahedron Lett. , 45 : 5419 – 5424 .
  • Lee , J. C. , Lee , J. Y. and Lee , S. J. 2004 . Efficient oxidation of benzylic alcohols with [hydroxy(tosyloxy)iodo]benzene under microwave irradiation . Tetrahedron Lett. , 45 : 4939 – 4941 .
  • Reddy , S. R. , Das , S. and Punniyamurthy , T. 2004 . Polyaniline supported vanadium catalyzed aerobic oxidation of alcohols to aldehydes and ketones . Tetrahedron Lett. , 45 : 3561 – 3564 .
  • Maiti , S. K. , Abdul Malik , K. M. and Bhattacharyya , R. 2004 . Oxoperxo‐molybdenum and ‐tungsten(VI) complexes: Their synthesis structure and catalytic uses in the peroxidic oxidation of alcohols to aldehydes and ketones . Inorg. Chem. Commun. , 7 : 823 – 828 .
  • Kassaee , M. Z. , Sayyed‐alangi , S. Z. and Sajjadi‐Ghottbabadi , H. 2004 . Synthesis and reactions of N‐methylbenzylammonium flurochromate(VI) on silica gel, a selective and efficient heterogeneous oxidant . Molecules , 9 : 825 – 829 .
  • Mallat , T. and Baiker , A. 2004 . Oxidation of alcohols with molecular oxygen on solid catalysts . Chem. Rev. , 104 : 3037 – 3058 . and references therein
  • Chhikara , B. S. , Chandra , R. and Tandon , V. 2005 . Oxidation of alcohols with hydrogen peroxide catalyzed by a new imidazolium ion based phosphotungstate in ionic liquid . J. Catal. , 230 : 436 – 439 .
  • Rajabi , F. and Karimi , B. 2005 . Efficient aerobic oxidation of benzylic alcohols using a novel combination N‐hydroxy phthalimide (NHPI) and a recyclable heterogeneous cobalt complex . J. Mol. Catal. A: Chem. , 46 : 95 – 99 .
  • Jiang , N. and Ragauskas , A. J. 2005 . TEMPO‐catalyzed oxidation of benzylic alcohols to aldehydes with the H2O2/HBr/ionic liquid[bmim]PF6 system . Tetrahedron Lett. , 46 : 3323 – 3326 .
  • Egami , H. , Shimizu , H. and Katsuki , T. 2005 . Aerobic oxidation of primary alcohols in the presence of activated secondary alcohols . Tetrahedron Lett. , 46 : 783 – 786 .
  • Ramachandraiah , G. , Ghosh , P. K. , Mehta , A. S. , Adimurthy , S. , Jethva , A. D. and Vaghela , S. S. U.S. Patent No. 6,740,253 . May 25, 2004 .
  • Ramachandraiah , G. , Ghosh , P. K. , Adimurthy , S. , Bedekar , A. V. and Shukla , D. B. U.S. Patent Appl . No. 10/449723 . May 30, 2003 . PCT Publication No. WO 2004/106227, December 9, 2004; Indian Patent No. 194811, May 30, 2003
  • Adimurthy , S. , Ramachandraiah , G. , Bedekar , A. V. , Ghosh , S. , Ranu , B. C. and Ghosh , P. K. 2006 . Eco‐friendly and versatile brominating reagent prepared from liquid bromine precursor . Green Chem. , 8 916–922; 10.1039/b606586d

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.