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Volumn 344, Issue 3-4, 2002, Pages 328-337

Facile and Clean Oxidation of Alcohols in Water Using Hypervalent Iodine (III) Reagents

Author keywords

Alcohols; Hypervalent compounds; Iodine; Oxidation; Water as solvent

Indexed keywords


EID: 0000940643     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/1615-4169(200206)344:3/4<328::AID-ADSC328>3.0.CO;2-S     Document Type: Article
Times cited : (104)

References (72)
  • 3
    • 0030725046 scopus 로고    scopus 로고
    • b) I. E. Markó, M. Tsukazaki, P. R. Giles, S. M. Brown, C. J. Urch, Angew. Chem. Int. Ed. Engl. 1997, 36, 2208-2210; Angew. Chem. 1997, 109, 2297-2299;
    • (1997) Angew. Chem. , vol.109 , pp. 2297-2299
  • 7
    • 0001213492 scopus 로고    scopus 로고
    • Recent reviews see: a) P. J. Stang, V. V. Zhdankin, Chem. Rev. 1996, 96, 1123-1178; b) A. Varvoglis, Hypervalent Iodine in Organic Synthesis, Academic Press, San Diego, 1997; c) T. Kitamura, Y. Fujiwara, Org. Prep. Proc. Int. 1997, 29, 409-458; d) T. Wirth, U. H. Hirt, Synthesis 1999, 1271-1287.
    • (1996) Chem. Rev. , vol.96 , pp. 1123-1178
    • Stang, P.J.1    Zhdankin, V.V.2
  • 8
    • 0001213492 scopus 로고    scopus 로고
    • Academic Press, San Diego
    • Recent reviews see: a) P. J. Stang, V. V. Zhdankin, Chem. Rev. 1996, 96, 1123-1178; b) A. Varvoglis, Hypervalent Iodine in Organic Synthesis, Academic Press, San Diego, 1997; c) T. Kitamura, Y. Fujiwara, Org. Prep. Proc. Int. 1997, 29, 409-458; d) T. Wirth, U. H. Hirt, Synthesis 1999, 1271-1287.
    • (1997) Hypervalent Iodine in Organic Synthesis
    • Varvoglis, A.1
  • 9
    • 0031502047 scopus 로고    scopus 로고
    • Recent reviews see: a) P. J. Stang, V. V. Zhdankin, Chem. Rev. 1996, 96, 1123-1178; b) A. Varvoglis, Hypervalent Iodine in Organic Synthesis, Academic Press, San Diego, 1997; c) T. Kitamura, Y. Fujiwara, Org. Prep. Proc. Int. 1997, 29, 409-458; d) T. Wirth, U. H. Hirt, Synthesis 1999, 1271-1287.
    • (1997) Org. Prep. Proc. Int. , vol.29 , pp. 409-458
    • Kitamura, T.1    Fujiwara, Y.2
  • 10
    • 0032821239 scopus 로고    scopus 로고
    • Recent reviews see: a) P. J. Stang, V. V. Zhdankin, Chem. Rev. 1996, 96, 1123-1178; b) A. Varvoglis, Hypervalent Iodine in Organic Synthesis, Academic Press, San Diego, 1997; c) T. Kitamura, Y. Fujiwara, Org. Prep. Proc. Int. 1997, 29, 409-458; d) T. Wirth, U. H. Hirt, Synthesis 1999, 1271-1287.
    • (1999) Synthesis , pp. 1271-1287
    • Wirth, T.1    Hirt, U.H.2
  • 15
    • 0035800351 scopus 로고    scopus 로고
    • c) T. Wirth, Angew. Chem. Int. Ed. 2001, 40, 2812-2814; Angew. Chem. 2001, 113, 2889-2892.
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 2812-2814
    • Wirth, T.1
  • 16
    • 0035800351 scopus 로고    scopus 로고
    • c) T. Wirth, Angew. Chem. Int. Ed. 2001, 40, 2812-2814; Angew. Chem. 2001, 113, 2889-2892.
    • (2001) Angew. Chem. , vol.113 , pp. 2889-2892
  • 17
    • 0001284394 scopus 로고
    • Our recent work: a) Y. Kita, H. Tohma, K. Hatanaka, T. Takada, S. Fujita, S. Mitoh, H. Sakurai, S. Oka, J. Am. Chem. Soc. 1994, 116, 3684-3691; b) Y. Kita, M. Arisawa, M. Gyoten, M. Nakajima, R. Hamada, H. Tohma, T. Takada, J. Org. Chem. 1998, 63, 6625-6633; c) T. Takada, M. Arisawa, M. Gyoten, R. Hamada, H. Tohma, Y. Kita, J. Org. Chem. 1998, 63, 7698-7706; d) Y. Kita, M. Egi, T. Takada, H. Tohma, Synthesis 1999, 885-897; e) M. Arisawa, S. Utsumi, M. Nakajima, N. G. Ramesh, H. Tohma, Y. Kita, Chem. Commun. 1999, 469-470, and references cited therein.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 3684-3691
    • Kita, Y.1    Tohma, H.2    Hatanaka, K.3    Takada, T.4    Fujita, S.5    Mitoh, S.6    Sakurai, H.7    Oka, S.8
  • 18
    • 0000247985 scopus 로고    scopus 로고
    • Our recent work: a) Y. Kita, H. Tohma, K. Hatanaka, T. Takada, S. Fujita, S. Mitoh, H. Sakurai, S. Oka, J. Am. Chem. Soc. 1994, 116, 3684-3691; b) Y. Kita, M. Arisawa, M. Gyoten, M. Nakajima, R. Hamada, H. Tohma, T. Takada, J. Org. Chem. 1998, 63, 6625-6633; c) T. Takada, M. Arisawa, M. Gyoten, R. Hamada, H. Tohma, Y. Kita, J. Org. Chem. 1998, 63, 7698-7706; d) Y. Kita, M. Egi, T. Takada, H. Tohma, Synthesis 1999, 885-897; e) M. Arisawa, S. Utsumi, M. Nakajima, N. G. Ramesh, H. Tohma, Y. Kita, Chem. Commun. 1999, 469-470, and references cited therein.
    • (1998) J. Org. Chem. , vol.63 , pp. 6625-6633
    • Kita, Y.1    Arisawa, M.2    Gyoten, M.3    Nakajima, M.4    Hamada, R.5    Tohma, H.6    Takada, T.7
  • 19
    • 0001158731 scopus 로고    scopus 로고
    • Our recent work: a) Y. Kita, H. Tohma, K. Hatanaka, T. Takada, S. Fujita, S. Mitoh, H. Sakurai, S. Oka, J. Am. Chem. Soc. 1994, 116, 3684-3691; b) Y. Kita, M. Arisawa, M. Gyoten, M. Nakajima, R. Hamada, H. Tohma, T. Takada, J. Org. Chem. 1998, 63, 6625-6633; c) T. Takada, M. Arisawa, M. Gyoten, R. Hamada, H. Tohma, Y. Kita, J. Org. Chem. 1998, 63, 7698-7706; d) Y. Kita, M. Egi, T. Takada, H. Tohma, Synthesis 1999, 885-897; e) M. Arisawa, S. Utsumi, M. Nakajima, N. G. Ramesh, H. Tohma, Y. Kita, Chem. Commun. 1999, 469-470, and references cited therein.
    • (1998) J. Org. Chem. , vol.63 , pp. 7698-7706
    • Takada, T.1    Arisawa, M.2    Gyoten, M.3    Hamada, R.4    Tohma, H.5    Kita, Y.6
  • 20
    • 0032963407 scopus 로고    scopus 로고
    • Our recent work: a) Y. Kita, H. Tohma, K. Hatanaka, T. Takada, S. Fujita, S. Mitoh, H. Sakurai, S. Oka, J. Am. Chem. Soc. 1994, 116, 3684-3691; b) Y. Kita, M. Arisawa, M. Gyoten, M. Nakajima, R. Hamada, H. Tohma, T. Takada, J. Org. Chem. 1998, 63, 6625-6633; c) T. Takada, M. Arisawa, M. Gyoten, R. Hamada, H. Tohma, Y. Kita, J. Org. Chem. 1998, 63, 7698-7706; d) Y. Kita, M. Egi, T. Takada, H. Tohma, Synthesis 1999, 885-897; e) M. Arisawa, S. Utsumi, M. Nakajima, N. G. Ramesh, H. Tohma, Y. Kita, Chem. Commun. 1999, 469-470, and references cited therein.
    • (1999) Synthesis , pp. 885-897
    • Kita, Y.1    Egi, M.2    Takada, T.3    Tohma, H.4
  • 21
    • 0033531471 scopus 로고    scopus 로고
    • and references cited therein
    • Our recent work: a) Y. Kita, H. Tohma, K. Hatanaka, T. Takada, S. Fujita, S. Mitoh, H. Sakurai, S. Oka, J. Am. Chem. Soc. 1994, 116, 3684-3691; b) Y. Kita, M. Arisawa, M. Gyoten, M. Nakajima, R. Hamada, H. Tohma, T. Takada, J. Org. Chem. 1998, 63, 6625-6633; c) T. Takada, M. Arisawa, M. Gyoten, R. Hamada, H. Tohma, Y. Kita, J. Org. Chem. 1998, 63, 7698-7706; d) Y. Kita, M. Egi, T. Takada, H. Tohma, Synthesis 1999, 885-897; e) M. Arisawa, S. Utsumi, M. Nakajima, N. G. Ramesh, H. Tohma, Y. Kita, Chem. Commun. 1999, 469-470, and references cited therein.
    • (1999) Chem. Commun. , pp. 469-470
    • Arisawa, M.1    Utsumi, S.2    Nakajima, M.3    Ramesh, N.G.4    Tohma, H.5    Kita, Y.6
  • 23
    • 0034599884 scopus 로고    scopus 로고
    • H. Tohma, S. Takizawa, T. Maegawa, Y. Kita, Angew. Chem. Int. Ed. 2000, 39, 1306-1308; Angew. Chem. 2000, 112, 1364-1368.
    • (2000) Angew. Chem. , vol.112 , pp. 1364-1368
  • 35
    • 0002906404 scopus 로고
    • The effects of halide ion have been reported by several groups; a) T. Shono, Y. Matsumura, J. Hayashi, M. Mizoguchi, Tetrahedron Lett. 1979, 165-168; b) P. A. Evans, T. A. Brandt, J. Org. Chem. 1997, 62, 5321-5326; c) S. D. Rychnovsky, R. Vaidyanathan, J. Org. Chem. 1999, 64, 310-312; d) J. H. Espenson, Z. Zhu, T. H. Zauche, J. Org. Chem. 1999, 64, 1191-1196; e) H. Tohma, S. Takizawa, H. Morioka, T. Maegawa, Y. Kita, Chem. Pharm. Bull. 2000, 48, 445-446.
    • (1979) Tetrahedron Lett. , pp. 165-168
    • Shono, T.1    Matsumura, Y.2    Hayashi, J.3    Mizoguchi, M.4
  • 36
    • 0000110682 scopus 로고    scopus 로고
    • The effects of halide ion have been reported by several groups; a) T. Shono, Y. Matsumura, J. Hayashi, M. Mizoguchi, Tetrahedron Lett. 1979, 165-168; b) P. A. Evans, T. A. Brandt, J. Org. Chem. 1997, 62, 5321-5326; c) S. D. Rychnovsky, R. Vaidyanathan, J. Org. Chem. 1999, 64, 310-312; d) J. H. Espenson, Z. Zhu, T. H. Zauche, J. Org. Chem. 1999, 64, 1191-1196; e) H. Tohma, S. Takizawa, H. Morioka, T. Maegawa, Y. Kita, Chem. Pharm. Bull. 2000, 48, 445-446.
    • (1997) J. Org. Chem. , vol.62 , pp. 5321-5326
    • Evans, P.A.1    Brandt, T.A.2
  • 37
    • 0033534673 scopus 로고    scopus 로고
    • The effects of halide ion have been reported by several groups; a) T. Shono, Y. Matsumura, J. Hayashi, M. Mizoguchi, Tetrahedron Lett. 1979, 165-168; b) P. A. Evans, T. A. Brandt, J. Org. Chem. 1997, 62, 5321-5326; c) S. D. Rychnovsky, R. Vaidyanathan, J. Org. Chem. 1999, 64, 310-312; d) J. H. Espenson, Z. Zhu, T. H. Zauche, J. Org. Chem. 1999, 64, 1191-1196; e) H. Tohma, S. Takizawa, H. Morioka, T. Maegawa, Y. Kita, Chem. Pharm. Bull. 2000, 48, 445-446.
    • (1999) J. Org. Chem. , vol.64 , pp. 310-312
    • Rychnovsky, S.D.1    Vaidyanathan, R.2
  • 38
    • 0033582657 scopus 로고    scopus 로고
    • The effects of halide ion have been reported by several groups; a) T. Shono, Y. Matsumura, J. Hayashi, M. Mizoguchi, Tetrahedron Lett. 1979, 165-168; b) P. A. Evans, T. A. Brandt, J. Org. Chem. 1997, 62, 5321-5326; c) S. D. Rychnovsky, R. Vaidyanathan, J. Org. Chem. 1999, 64, 310-312; d) J. H. Espenson, Z. Zhu, T. H. Zauche, J. Org. Chem. 1999, 64, 1191-1196; e) H. Tohma, S. Takizawa, H. Morioka, T. Maegawa, Y. Kita, Chem. Pharm. Bull. 2000, 48, 445-446.
    • (1999) J. Org. Chem. , vol.64 , pp. 1191-1196
    • Espenson, J.H.1    Zhu, Z.2    Zauche, T.H.3
  • 39
    • 0034034737 scopus 로고    scopus 로고
    • The effects of halide ion have been reported by several groups; a) T. Shono, Y. Matsumura, J. Hayashi, M. Mizoguchi, Tetrahedron Lett. 1979, 165-168; b) P. A. Evans, T. A. Brandt, J. Org. Chem. 1997, 62, 5321-5326; c) S. D. Rychnovsky, R. Vaidyanathan, J. Org. Chem. 1999, 64, 310-312; d) J. H. Espenson, Z. Zhu, T. H. Zauche, J. Org. Chem. 1999, 64, 1191-1196; e) H. Tohma, S. Takizawa, H. Morioka, T. Maegawa, Y. Kita, Chem. Pharm. Bull. 2000, 48, 445-446.
    • (2000) Chem. Pharm. Bull. , vol.48 , pp. 445-446
    • Tohma, H.1    Takizawa, S.2    Morioka, H.3    Maegawa, T.4    Kita, Y.5
  • 43
    • 0346314505 scopus 로고    scopus 로고
    • The reaction took longer (24 h) to complete when the concentration of 1u in water was 0.2 M
    • The reaction took longer (24 h) to complete when the concentration of 1u in water was 0.2 M.
  • 47
    • 0033520316 scopus 로고    scopus 로고
    • a) A. Kirschning, H. Monenschein, C. Schmeck, Angew. Chem. Int. Ed. 1999, 38, 2594-2596; Angew. Chem. 1999, 111, 2720-2722;
    • (1999) Angew. Chem. , vol.111 , pp. 2720-2722
  • 50
    • 0034533265 scopus 로고    scopus 로고
    • Reviews see: a) S. V. Ley, I. R. Baxendale, R. N. Bream, P. S. Jackson, A. G. Leach, D. A. Longbottom, M. Nesi, J. S. Scott, R. I. Storer, S. J. Taylor, J. Chem. Soc. Perkin Trans. 1, 2000, 3815-4195; b) G. Bhalay, A. Dunstan, A. Glen, Synlett 2000, 1846-1859; c) A. Kirschning, H. Monenschein, R. Wittenberg, Angew. Chem. Int. Ed. 2001, 40, 650-679; Angew. Chem. 2001, 113, 670-701.
    • (2000) Synlett , pp. 1846-1859
    • Bhalay, G.1    Dunstan, A.2    Glen, A.3
  • 51
    • 0035804384 scopus 로고    scopus 로고
    • Reviews see: a) S. V. Ley, I. R. Baxendale, R. N. Bream, P. S. Jackson, A. G. Leach, D. A. Longbottom, M. Nesi, J. S. Scott, R. I. Storer, S. J. Taylor, J. Chem. Soc. Perkin Trans. 1, 2000, 3815-4195; b) G. Bhalay, A. Dunstan, A. Glen, Synlett 2000, 1846-1859; c) A. Kirschning, H. Monenschein, R. Wittenberg, Angew. Chem. Int. Ed. 2001, 40, 650-679; Angew. Chem. 2001, 113, 670-701.
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 650-679
    • Kirschning, A.1    Monenschein, H.2    Wittenberg, R.3
  • 52
    • 0001568265 scopus 로고    scopus 로고
    • Reviews see: a) S. V. Ley, I. R. Baxendale, R. N. Bream, P. S. Jackson, A. G. Leach, D. A. Longbottom, M. Nesi, J. S. Scott, R. I. Storer, S. J. Taylor, J. Chem. Soc. Perkin Trans. 1, 2000, 3815-4195; b) G. Bhalay, A. Dunstan, A. Glen, Synlett 2000, 1846-1859; c) A. Kirschning, H. Monenschein, R. Wittenberg, Angew. Chem. Int. Ed. 2001, 40, 650-679; Angew. Chem. 2001, 113, 670-701.
    • (2001) Angew. Chem. , vol.113 , pp. 670-701
  • 59
    • 0001441892 scopus 로고
    • The method for preparing PDAIS was originally reported by Okawara in 1961, and was also reported independently by Hallensleben; a) M. Okawara, K. Mizuta, Kogyo Kagaku Zasshi 1961, 64, 232-235; b) Y. Yamada, M. Okawara, Makromol. Chem. 1972, 152, 153-162; c) M. L. Hallensleben, Angew. Makromol. Chem. 1972, 27, 223-227.
    • (1961) Kogyo Kagaku Zasshi , vol.64 , pp. 232-235
    • Okawara, M.1    Mizuta, K.2
  • 60
    • 0001419776 scopus 로고
    • The method for preparing PDAIS was originally reported by Okawara in 1961, and was also reported independently by Hallensleben; a) M. Okawara, K. Mizuta, Kogyo Kagaku Zasshi 1961, 64, 232-235; b) Y. Yamada, M. Okawara, Makromol. Chem. 1972, 152, 153-162; c) M. L. Hallensleben, Angew. Makromol. Chem. 1972, 27, 223-227.
    • (1972) Makromol. Chem. , vol.152 , pp. 153-162
    • Yamada, Y.1    Okawara, M.2
  • 61
    • 84981894440 scopus 로고
    • The method for preparing PDAIS was originally reported by Okawara in 1961, and was also reported independently by Hallensleben; a) M. Okawara, K. Mizuta, Kogyo Kagaku Zasshi 1961, 64, 232-235; b) Y. Yamada, M. Okawara, Makromol. Chem. 1972, 152, 153-162; c) M. L. Hallensleben, Angew. Makromol. Chem. 1972, 27, 223-227.
    • (1972) Angew. Makromol. Chem. , vol.27 , pp. 223-227
    • Hallensleben, M.L.1
  • 63
    • 0346944690 scopus 로고    scopus 로고
    • Even after stirring PDAIS in water for 4 days, the addition of 1e and KBr to this suspension gave 2e in 68% yield
    • Even after stirring PDAIS in water for 4 days, the addition of 1e and KBr to this suspension gave 2e in 68% yield.
  • 64
    • 0347575566 scopus 로고    scopus 로고
    • note
    • - as a bromide ion source. However, addition of a catalytic amount of water to the above-mentioned mixture enhanced the yield of 2e to 51%.


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