메뉴 건너뛰기




Volumn 131, Issue 1, 2009, Pages 251-262

2-iodoxybenzenesulfonic acid as an extremely active catalyst for the selective oxidation of alcohols to aldehydes, ketones, carboxylic acids, and enones with oxone

Author keywords

[No Author keywords available]

Indexed keywords

2-IODOXYBENZOIC ACID; ACTIVE CATALYST; CARBONYL COMPOUNDS; CYCLOALKANONES; CYCLOALKENONES; ELECTRON-DONATING GROUP; ETHYL ACETATES; HYPERVALENT IODINE; IN-SITU; IONIC CHARACTER; NITROMETHANE; NON-AQUEOUS; OXIDATION OF ALCOHOLS; SECONDARY ALCOHOLS; SELECTIVE OXIDATION; SODIUM SALT; THEORETICAL CALCULATIONS;

EID: 67749120518     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja807110n     Document Type: Article
Times cited : (283)

References (58)
  • 4
    • 0000676907 scopus 로고    scopus 로고
    • 3rd ed, Pergamon: Oxford, Chap. 2, pp
    • (d) Ley, S. V. Comprehensive Organic Synthesis, 3rd ed.; Pergamon: Oxford, 1999; Vol. 7, Chap. 2, pp 251-327.
    • (1999) Comprehensive Organic Synthesis , vol.7 , pp. 251-327
    • Ley, S.V.1
  • 14
    • 0001510286 scopus 로고
    • For the first preparation of IBX, see
    • For the first preparation of IBX, see: Hartman, C.; Meyer, V. Chem. Ber. 1893, 26, 1727.
    • (1893) Chem. Ber , vol.26 , pp. 1727
    • Hartman, C.1    Meyer, V.2
  • 15
    • 0027988788 scopus 로고
    • For Nicolaou's excellent works with IBX, see: For the first use of IBX as a selective oxidant for alcohols, see: a
    • For the first use of IBX as a selective oxidant for alcohols, see: (a) Frigerio, M.; Santagostino, M. Tetrahedron Lett. 1994, 35, 8019. For Nicolaou's excellent works with IBX, see:
    • (1994) Tetrahedron Lett , vol.35 , pp. 8019
    • Frigerio, M.1    Santagostino, M.2
  • 19
    • 1942536050 scopus 로고    scopus 로고
    • For recent reviews focused on hypervalent iodine chemistry, see
    • (e) Nicolaou, K. C.; Mathison, C. J. N.; Montagnon, T. J. Am. Chem. Soc. 2004, 126, 5192. For recent reviews focused on hypervalent iodine chemistry, see:
    • (2004) J. Am. Chem. Soc , vol.126 , pp. 5192
    • Nicolaou, K.C.1    Mathison, C.J.N.2    Montagnon, T.3
  • 21
    • 0037664955 scopus 로고    scopus 로고
    • Wiley-VCH: Weinheim, For recent reviews focused on hypervalent idine chemistry, see
    • (g) Wirth, T. Organic Synthesis Highlights V; Wiley-VCH: Weinheim, 2003; p 144. For recent reviews focused on hypervalent idine chemistry, see:
    • (2003) Organic Synthesis Highlights V , pp. 144
    • Wirth, T.1
  • 25
    • 67849120801 scopus 로고    scopus 로고
    • Ladziata, U.; Zhdankin, V. V. ARKIVOC 2006, ix, 26. (l) Ochiai, M.; Miyamota, K. Eur. J. Org. Chem. 2008, 4229.
    • (k) Ladziata, U.; Zhdankin, V. V. ARKIVOC 2006, ix, 26. (l) Ochiai, M.; Miyamota, K. Eur. J. Org. Chem. 2008, 4229.
  • 42
    • 33847088881 scopus 로고    scopus 로고
    • For the synthesis of 7a, see: (a) Chau, M. M.; Kice, J. L. J. Org. Chem. 1977, 42, 3265.
    • For the synthesis of 7a, see: (a) Chau, M. M.; Kice, J. L. J. Org. Chem. 1977, 42, 3265.
  • 44
    • 67849098628 scopus 로고    scopus 로고
    • WO2001008674, is commercially available from CarboMer, Inc, San Diego, CA
    • (c) Minami, T.; Ito, S.; Ohuchida, S.; Naganawa, A.; Maruyama, T. PCT Int. Appl. 2001, WO2001008674. 7a is commercially available from CarboMer, Inc. (San Diego, CA).
    • (2001) PCT Int. Appl , vol.7 a
    • Minami, T.1    Ito, S.2    Ohuchida, S.3    Naganawa, A.4    Maruyama, T.5
  • 46
    • 34047201372 scopus 로고    scopus 로고
    • 3- iodanes by strong Lewis acids that increased its oxidation power. For a review, see: Ochiai, M
    • 3- iodanes by strong Lewis acids that increased its oxidation power. For a review, see: Ochiai, M. Chem. Rec. 2007, 7,12.
    • (2007) Chem. Rec , vol.7 , pp. 12
  • 47
    • 67849100561 scopus 로고    scopus 로고
    • TON and TOF are based on precatalysts 2 and 7.
    • TON and TOF are based on precatalysts 2 and 7.
  • 48
    • 0003543593 scopus 로고    scopus 로고
    • For the synthesis of α,β-unsaturated carbonyl compounds, see: a, John Wiley & Sons: New York
    • For the synthesis of α,β-unsaturated carbonyl compounds, see: (a) Larock, R. C. Comprehensive Organic Transformations; John Wiley & Sons: New York, 1999; pp 251-256.
    • (1999) Comprehensive Organic Transformations , pp. 251-256
    • Larock, R.C.1
  • 50
    • 0001474572 scopus 로고
    • For the oxidation of alicyclic ketones with Oxone in the presence of wet-alumina to the lactones, see
    • For the oxidation of alicyclic ketones with Oxone in the presence of wet-alumina to the lactones, see: Hirano, M.; Oose, M.; Morimoto, T. Chem. Lett. 1991, 331.
    • (1991) Chem. Lett , pp. 331
    • Hirano, M.1    Oose, M.2    Morimoto, T.3
  • 51
    • 33947291370 scopus 로고    scopus 로고
    • To the best of our knowledge, there are only two examples on the direct catalytic oxidative dehydrogenation of carbonyl compounds. (a) Pd catalyst with Cu co-catalyst: Theissen, R. J. J. Org. Chem. 1971, 36, 752.
    • To the best of our knowledge, there are only two examples on the direct catalytic oxidative dehydrogenation of carbonyl compounds. (a) Pd catalyst with Cu co-catalyst: Theissen, R. J. J. Org. Chem. 1971, 36, 752.
  • 52
    • 0001609793 scopus 로고    scopus 로고
    • Pd catalyst with stoichiometric allyl diethyl phosphate reagents in the presence of stoichiometric bases: Shvo, Y, Arisha, A. H. I. J. Org. Chem. 1998, 63, 5640
    • (b) Pd catalyst with stoichiometric allyl diethyl phosphate reagents in the presence of stoichiometric bases: Shvo, Y.; Arisha, A. H. I. J. Org. Chem. 1998, 63, 5640.
  • 54
    • 67849112774 scopus 로고    scopus 로고
    • Frisch, M. J.; et al. Gaussian 03, revision D.02; Gaussian, Inc.: Wallingford, CT, 2004.
    • Frisch, M. J.; et al. Gaussian 03, revision D.02; Gaussian, Inc.: Wallingford, CT, 2004.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.