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Volumn 9, Issue 4, 2005, Pages 341-351

A practical synthesis of a high-loading solid-supported IBX amide for the oxidation of alcohols

Author keywords

Alcohols; IBX resin; Immobilised reagents; Oxidation

Indexed keywords

2 IODOBENZOIC ACID; 2 IODYLBENZOIC ACID; ALCOHOL DERIVATIVE; AMIDE; BENZOIC ACID DERIVATIVE; CARBONYL DERIVATIVE; RESIN; UNCLASSIFIED DRUG;

EID: 28344457207     PISSN: 13811991     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11030-005-8105-2     Document Type: Article
Times cited : (22)

References (26)
  • 1
    • 56249137056 scopus 로고
    • Ueber Jodo Benzoësäure
    • Hartman, C. and Mayer, V., Ueber Jodo Benzoësäure, Chem. Ber., 26 (1893) 1727-1732.
    • (1893) Chem. Ber. , vol.26 , pp. 1727-1732
    • Hartman, C.1    Mayer, V.2
  • 2
    • 33644528891 scopus 로고
    • Readily accessible 12-I-5 oxidant for the conversion of primary and secondary alcohols to aldehydes and ketones
    • Dess, D.B. and Martin, J.C., Readily accessible 12-I-5 oxidant for the conversion of primary and secondary alcohols to aldehydes and ketones. J. Org. Chem., 48 (1983) 4155-4156.
    • (1983) J. Org. Chem. , vol.48 , pp. 4155-4156
    • Dess, D.B.1    Martin, J.C.2
  • 3
    • 0027988788 scopus 로고
    • A mild oxidizing reagent for alcohols and 1,2-diols: O-iodoxybenzoic acid (IBX) in DMSO
    • (a) Frigerio, M. and Santagostino, M., A mild oxidizing reagent for alcohols and 1,2-diols: o-iodoxybenzoic acid (IBX) in DMSO, Tetrahedron Lett., 35 (1994) 8019-8022.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 8019-8022
    • Frigerio, M.1    Santagostino, M.2
  • 4
    • 0000295212 scopus 로고
    • Oxidation of alcohols with o-iodoxybenzoic acid in DMSO: A new insight into an old hypervalent iodine reagent
    • (b) Frigerio, M., Santagostino, M., Sputore, S. and Palmisano, G., Oxidation of alcohols with o-iodoxybenzoic acid in DMSO: A new insight into an old hypervalent iodine reagent, J. Org. Chem., 60 (1995) 7272-7276.
    • (1995) J. Org. Chem. , vol.60 , pp. 7272-7276
    • Frigerio, M.1    Santagostino, M.2    Sputore, S.3    Palmisano, G.4
  • 5
    • 0035800351 scopus 로고    scopus 로고
    • IBX-New reactions with an old reagent
    • (a) Wirth, T., IBX-New reactions with an old reagent, Angew. Chem. Int. Ed., 40 (2001) 2812-2814.
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 2812-2814
    • Wirth, T.1
  • 6
    • 0037070584 scopus 로고    scopus 로고
    • Iodine(V) reagents in organic synthesis. Part 3. New routes to heterocyclic compounds via o-iodoxybenzoic acid-mediated cyclizations: Generality, scope, and mechanism
    • (b). Nicolaou, K.C., Baran, P.S., Zhong, Y.-L., Barluenga, S., Hunt, W.K., Kranich, R. and Vega, J.A., Iodine(V) reagents in organic synthesis. Part 3. New routes to heterocyclic compounds via o-iodoxybenzoic acid-mediated cyclizations: generality, scope, and mechanism, J. Am. Chem. Soc., 124 (2002) 2233-2244.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 2233-2244
    • Nicolaou, K.C.1    Baran, P.S.2    Zhong, Y.-L.3    Barluenga, S.4    Hunt, W.K.5    Kranich, R.6    Vega, J.A.7
  • 7
    • 0037070535 scopus 로고    scopus 로고
    • Iodine(V) reagents in organic synthesis. Part 4. o-Iodoxybenzoic acid as a chemospecific tool for single electron transfer-based oxidation processes
    • (c) Nicolaou, K.C., Montagnon, T., Baran, P.S. and Zhong, Y.-L., Iodine(V) reagents in organic synthesis. Part 4. o-Iodoxybenzoic acid as a chemospecific tool for single electron transfer-based oxidation processes, J. Am. Chem. Soc., 124 (2002) 2245-2258.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 2245-2258
    • Nicolaou, K.C.1    Montagnon, T.2    Baran, P.S.3    Zhong, Y.-L.4
  • 8
    • 0037182709 scopus 로고    scopus 로고
    • Facile cleavage of triethylsilyl (TES) ethers using o-iodoxybenzoic acid (IBX) without affecting tert-butyldimethylsilyl (TBS) ethers
    • (d) Wu, Y., Huang, J.-H., Shen, X., Hu, Q. Tang, C.-J. and Li, L., Facile cleavage of triethylsilyl (TES) ethers using o-iodoxybenzoic acid (IBX) without affecting tert-butyldimethylsilyl (TBS) ethers, Org. Lett., 4 (2002) 2141-2144.
    • (2002) Org. Lett. , vol.4 , pp. 2141-2144
    • Wu, Y.1    Huang, J.-H.2    Shen, X.3    Hu, Q.4    Tang, C.-J.5    Li, L.6
  • 9
    • 0002380120 scopus 로고
    • 2-Iodoxybenzoic acid
    • (a) Plumb, J.B. and Harper, D.J., 2-Iodoxybenzoic acid, Chem. Eng. News, 68(29) (1990) 3.
    • (1990) Chem. Eng. News , vol.68 , Issue.29 , pp. 3
    • Plumb, J.B.1    Harper, D.J.2
  • 10
    • 3042741556 scopus 로고
    • A useful 12-I-5 triacetoxyperiodinane (the Dess-Martin Periodinane) for the selective oxidation of primaiy or secondary alcohols and a variety of related 12-I-5 species
    • (b) The tested IBX was certainly contaminated by bromine which gave a more explosive sample, see note 3e in Dess, D.B. and Martin, J.C., A useful 12-I-5 triacetoxyperiodinane (the Dess-Martin Periodinane) for the selective oxidation of primaiy or secondary alcohols and a variety of related 12-I-5 species, J. Am. Chem. Soc., 113 (1991) 7277-7287.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 7277-7287
    • Dess, D.B.1    Martin, J.C.2
  • 11
    • 0000234498 scopus 로고    scopus 로고
    • A simple and advantageous protocol for the oxidation of alcohols with o-iodoxybenzoic acid (IBX)
    • More, J.D. and Finney, N.S., A simple and advantageous protocol for the oxidation of alcohols with o-iodoxybenzoic acid (IBX), Org. Lett., 4 (2002) 3001-3003.
    • (2002) Org. Lett. , vol.4 , pp. 3001-3003
    • More, J.D.1    Finney, N.S.2
  • 12
    • 0141521516 scopus 로고    scopus 로고
    • Mild oxidation of alcohols with o-iodoxybenzoic acid (IBX) in ionic liquid 1-butyl-3-methyl-imidazolium chloride and water
    • Liu, Z., Chen, Z. and Zheng, Q., Mild oxidation of alcohols with o-iodoxybenzoic acid (IBX) in ionic liquid 1-butyl-3-methyl-imidazolium chloride and water, Org. Lett., 5 (2003) 3321-3323.
    • (2003) Org. Lett. , vol.5 , pp. 3321-3323
    • Liu, Z.1    Chen, Z.2    Zheng, Q.3
  • 13
    • 0037147937 scopus 로고    scopus 로고
    • Synthesis and oxidation reactions of a user- and eco-friendly hypervalent iodine reagent
    • Thottumkara, A.P. and Vinod, T.K., Synthesis and oxidation reactions of a user- and eco-friendly hypervalent iodine reagent. Tetrahedron Lett., 43 (2002) 569-572.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 569-572
    • Thottumkara, A.P.1    Vinod, T.K.2
  • 15
    • 0035803743 scopus 로고    scopus 로고
    • Oxidizing polymers: A polymer-supported, recyclable hypervalent iodine(V) reagent for the efficient conversion of alcohols, carbonyl compounds, and unsaturated carbamates in solution
    • (a) Sorg, G., Mengel, A., Jung, G. and Rademann, J., Oxidizing polymers: A polymer-supported, recyclable hypervalent iodine(V) reagent for the efficient conversion of alcohols, carbonyl compounds, and unsaturated carbamates in solution, Angew. Chem. Int. Ed., 40 (2001) 4395-4397.
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 4395-4397
    • Sorg, G.1    Mengel, A.2    Jung, G.3    Rademann, J.4
  • 17
    • 0035803642 scopus 로고    scopus 로고
    • The synthesis and oxidative properties of polymer-supported IBX
    • (c) Mülbaier, M. and Giannis, A., The synthesis and oxidative properties of polymer-supported IBX, Angew. Chem. Int. Ed., 40 (2001) 4393-4394.
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 4393-4394
    • Mülbaier, M.1    Giannis, A.2
  • 20
    • 0344873178 scopus 로고    scopus 로고
    • Simple preparation of polymer supported IBX esters and amides and their oxidative properties
    • (a) Chung, W.J., Kim, D.K. and Lee, Y.S., Simple preparation of polymer supported IBX esters and amides and their oxidative properties, Tetrahedron Lett., 44 (2003) 9251-9254.
    • (2003) Tetrahedron Lett. , vol.44 , pp. 9251-9254
    • Chung, W.J.1    Kim, D.K.2    Lee, Y.S.3
  • 21
    • 0031013326 scopus 로고    scopus 로고
    • Convenient method for preparing polystyrene having β-hydroxy group: Its application to the synthesis of polyethylene glycol grafted polystyrene resin
    • (b) Park, B.D., Lee, H.I., Ryoo, S.J. and Lee, Y.S., Convenient method for preparing polystyrene having β-hydroxy group: Its application to the synthesis of polyethylene glycol grafted polystyrene resin, Tetrahedron Lett., 38 (1997) 591-594.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 591-594
    • Park, B.D.1    Lee, H.I.2    Ryoo, S.J.3    Lee, Y.S.4
  • 22
    • 0042871535 scopus 로고    scopus 로고
    • Efficient methods of converting hydroxyl groups into amino groups in poly(ethylene glycol)-grafted polystyrene resin
    • (c) Ryoo, S.J., Kim, J., Kim, J.S. and Lee, Y.S., Efficient methods of converting hydroxyl groups into amino groups in poly(ethylene glycol)-grafted polystyrene resin, J. Comb. Chem., 4 (2002) 187-190.
    • (2002) J. Comb. Chem. , vol.4 , pp. 187-190
    • Ryoo, S.J.1    Kim, J.2    Kim, J.S.3    Lee, Y.S.4
  • 23
    • 28344456709 scopus 로고
    • Jodierte derivate der 3-aminomethyl-benzoesäure
    • Felder, E., Pitré, D. and Fumagalli, L., Jodierte derivate der 3-aminomethyl-benzoesäure, Helv. Chim. Acta, 48 (1965) 259-274.
    • (1965) Helv. Chim. Acta , vol.48 , pp. 259-274
    • Felder, E.1    Pitré, D.2    Fumagalli, L.3
  • 26
    • 28344440799 scopus 로고    scopus 로고
    • See supplementary material
    • For general conditions: See supplementary material.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.