메뉴 건너뛰기




Volumn 127, Issue 15, 2005, Pages 5396-5413

Ruthenium(salen)-catalyzed aerobic oxidative desymmetrizatin of meso-diols and its kinetics

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; CATALYSIS; DISSOCIATION; MOLECULAR STRUCTURE; REACTION KINETICS; RUTHENIUM;

EID: 17644416367     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja047608i     Document Type: Article
Times cited : (113)

References (100)
  • 1
    • 84941207157 scopus 로고
    • Morrison, J. D., Ed.; Academic Press: New York
    • (a) Jones, J. B. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 5, pp 309-344.
    • (1984) Asymmetric Synthesis , vol.5 , pp. 309-344
    • Jones, J.B.1
  • 4
    • 0012986006 scopus 로고    scopus 로고
    • Katsuki, T., Ed.; Oxford University Press: Oxford
    • (d) Fantin, G.; Pedrini, P. In Asymmetric Oxidation Reactions; Katsuki, T., Ed.; Oxford University Press: Oxford, 2001; pp 200-214.
    • (2001) Asymmetric Oxidation Reactions , pp. 200-214
    • Fantin, G.1    Pedrini, P.2
  • 23
    • 0037100264 scopus 로고    scopus 로고
    • A detailed mechanism of photo-activation of (ON)Ru(salen)Cl complex has been reported: (b) Works, C. F.; Jocher, C. J.; Bart, G. D.; Bu, X.; Ford, P. C. Inorg. Chem. 2002, 41, 3728-3739. (c) Works, C. F.; Ford, P. C. J. Am. Chem. Soc. 2000, 122, 7592-7593. (d) Bordini, J.; Hughes, D. L.; Da Motta Neto, J. D.; da Cunha, C. J. Inorg. Chem. 2002, 41, 5410-5416.
    • (2002) Inorg. Chem. , vol.41 , pp. 3728-3739
    • Works, C.F.1    Jocher, C.J.2    Bart, G.D.3    Bu, X.4    Ford, P.C.5
  • 24
    • 0034625887 scopus 로고    scopus 로고
    • A detailed mechanism of photo-activation of (ON)Ru(salen)Cl complex has been reported: (b) Works, C. F.; Jocher, C. J.; Bart, G. D.; Bu, X.; Ford, P. C. Inorg. Chem. 2002, 41, 3728-3739. (c) Works, C. F.; Ford, P. C. J. Am. Chem. Soc. 2000, 122, 7592-7593. (d) Bordini, J.; Hughes, D. L.; Da Motta Neto, J. D.; da Cunha, C. J. Inorg. Chem. 2002, 41, 5410-5416.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 7592-7593
    • Works, C.F.1    Ford, P.C.2
  • 25
    • 0037152394 scopus 로고    scopus 로고
    • A detailed mechanism of photo-activation of (ON)Ru(salen)Cl complex has been reported: (b) Works, C. F.; Jocher, C. J.; Bart, G. D.; Bu, X.; Ford, P. C. Inorg. Chem. 2002, 41, 3728-3739. (c) Works, C. F.; Ford, P. C. J. Am. Chem. Soc. 2000, 122, 7592-7593. (d) Bordini, J.; Hughes, D. L.; Da Motta Neto, J. D.; da Cunha, C. J. Inorg. Chem. 2002, 41, 5410-5416.
    • (2002) Inorg. Chem. , vol.41 , pp. 5410-5416
    • Bordini, J.1    Hughes, D.L.2    Da Motta Neto, J.D.3    Da Cunha, C.J.4
  • 28
    • 3142760224 scopus 로고    scopus 로고
    • Simandi, L. I., Ed.; Kluwer Academic Publishers: Dordrecht
    • For the review of aerobic oxidation of alcohols, see: (a) Sheldon, R. A. ; Arends, I. W. C. E. In Advances in Catalytic Activation of Dioxygen by Metal Complexes; Simandi, L. I., Ed.; Kluwer Academic Publishers: Dordrecht, 2003; pp 123-155. (b) Sigman, M. S.; Jensen, D. R.; Rajaram, S. Curr. Opin. Drug Discovery Dev. 2002, 5, 860-869. (c) Marcó, I. E.; Giles, P. R.; Tsukazaki, M.; Brown, S. M.; Urch, C. J. In Transition Metals for Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, 1999; Vol. 2, pp 350-360. (d) Nishimura, T.; Uemura, S. Synlett 2004, 201-216. (e) Stoltz, B. M. Chem. Lett. 2004, 33, 362-367.
    • (2003) Advances in Catalytic Activation of Dioxygen by Metal Complexes , pp. 123-155
    • Sheldon, R.A.1    Arends, I.W.C.E.2
  • 29
    • 0036869538 scopus 로고    scopus 로고
    • For the review of aerobic oxidation of alcohols, see: (a) Sheldon, R. A. ; Arends, I. W. C. E. In Advances in Catalytic Activation of Dioxygen by Metal Complexes; Simandi, L. I., Ed.; Kluwer Academic Publishers: Dordrecht, 2003; pp 123-155. (b) Sigman, M. S.; Jensen, D. R.; Rajaram, S. Curr. Opin. Drug Discovery Dev. 2002, 5, 860-869. (c) Marcó, I. E.; Giles, P. R.; Tsukazaki, M.; Brown, S. M.; Urch, C. J. In Transition Metals for Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, 1999; Vol. 2, pp 350-360. (d) Nishimura, T.; Uemura, S. Synlett 2004, 201-216. (e) Stoltz, B. M. Chem. Lett. 2004, 33, 362-367.
    • (2002) Curr. Opin. Drug Discovery Dev. , vol.5 , pp. 860-869
    • Sigman, M.S.1    Jensen, D.R.2    Rajaram, S.3
  • 30
    • 0002163941 scopus 로고    scopus 로고
    • Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim
    • For the review of aerobic oxidation of alcohols, see: (a) Sheldon, R. A. ; Arends, I. W. C. E. In Advances in Catalytic Activation of Dioxygen by Metal Complexes; Simandi, L. I., Ed.; Kluwer Academic Publishers: Dordrecht, 2003; pp 123-155. (b) Sigman, M. S.; Jensen, D. R.; Rajaram, S. Curr. Opin. Drug Discovery Dev. 2002, 5, 860-869. (c) Marcó, I. E.; Giles, P. R.; Tsukazaki, M.; Brown, S. M.; Urch, C. J. In Transition Metals for Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, 1999; Vol. 2, pp 350-360. (d) Nishimura, T.; Uemura, S. Synlett 2004, 201-216. (e) Stoltz, B. M. Chem. Lett. 2004, 33, 362-367.
    • (1999) Transition Metals for Organic Synthesis , vol.2 , pp. 350-360
    • Marcó, I.E.1    Giles, P.R.2    Tsukazaki, M.3    Brown, S.M.4    Urch, C.J.5
  • 31
    • 1342302388 scopus 로고    scopus 로고
    • For the review of aerobic oxidation of alcohols, see: (a) Sheldon, R. A. ; Arends, I. W. C. E. In Advances in Catalytic Activation of Dioxygen by Metal Complexes; Simandi, L. I., Ed.; Kluwer Academic Publishers: Dordrecht, 2003; pp 123-155. (b) Sigman, M. S.; Jensen, D. R.; Rajaram, S. Curr. Opin. Drug Discovery Dev. 2002, 5, 860-869. (c) Marcó, I. E.; Giles, P. R.; Tsukazaki, M.; Brown, S. M.; Urch, C. J. In Transition Metals for Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, 1999; Vol. 2, pp 350-360. (d) Nishimura, T.; Uemura, S. Synlett 2004, 201-216. (e) Stoltz, B. M. Chem. Lett. 2004, 33, 362-367.
    • (2004) Synlett , pp. 201-216
    • Nishimura, T.1    Uemura, S.2
  • 32
    • 3142737499 scopus 로고    scopus 로고
    • For the review of aerobic oxidation of alcohols, see: (a) Sheldon, R. A. ; Arends, I. W. C. E. In Advances in Catalytic Activation of Dioxygen by Metal Complexes; Simandi, L. I., Ed.; Kluwer Academic Publishers: Dordrecht, 2003; pp 123-155. (b) Sigman, M. S.; Jensen, D. R.; Rajaram, S. Curr. Opin. Drug Discovery Dev. 2002, 5, 860-869. (c) Marcó, I. E.; Giles, P. R.; Tsukazaki, M.; Brown, S. M.; Urch, C. J. In Transition Metals for Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, 1999; Vol. 2, pp 350-360. (d) Nishimura, T.; Uemura, S. Synlett 2004, 201-216. (e) Stoltz, B. M. Chem. Lett. 2004, 33, 362-367.
    • (2004) Chem. Lett. , vol.33 , pp. 362-367
    • Stoltz, B.M.1
  • 33
    • 0037027719 scopus 로고    scopus 로고
    • A part of this study has been communicated: (a) Shimizu, H.; Nakata, K.; Katsuki, T. Chem. Lett. 2002, 1080-1081. (b) Shimizu, H.; Katsuki, T. Chem. Lett. 2003, 480-481.
    • (2002) Chem. Lett. , pp. 1080-1081
    • Shimizu, H.1    Nakata, K.2    Katsuki, T.3
  • 34
    • 0041760730 scopus 로고    scopus 로고
    • A part of this study has been communicated: (a) Shimizu, H.; Nakata, K.; Katsuki, T. Chem. Lett. 2002, 1080-1081. (b) Shimizu, H.; Katsuki, T. Chem. Lett. 2003, 480-481.
    • (2003) Chem. Lett. , pp. 480-481
    • Shimizu, H.1    Katsuki, T.2
  • 40
    • 17644383036 scopus 로고    scopus 로고
    • note
    • -1 characteristic of the OH group, while those of 4 did not show such absorption.
  • 44
    • 17644422844 scopus 로고    scopus 로고
    • note
    • This working hypothesis was found to be inconsistent with the kinetic study: see the section for kinetic study.
  • 45
    • 17644367912 scopus 로고    scopus 로고
    • note
    • 1H NMR (400 MHz) analysis of the products indicated the formation of the acetals from the resulting aldehyde and the starting diol.
  • 58
    • 17644398272 scopus 로고    scopus 로고
    • note
    • The kinetic experimental protocol is given in the Experimental Section.
  • 59
    • 17644394998 scopus 로고    scopus 로고
    • note
    • This experiment was carried out according to the kind suggestions of a reviewer, to whom we are very grateful.
  • 68
    • 0002095610 scopus 로고
    • KIEs of 1.9-7 have been reported for cerium, vanadium, cobalt, manganese, and chromium-mediated oxidation via metal-alcoholate complexes: (a) Westheimer, F. H.; Nicolaides, N. J. Am. Chem. Soc. 1949, 71, 25-28. (b) Ardon, M. J. Chem. Soc. 1957, 1811-1815. (c) Litter, J. S.; Waters, W. A. J. Chem. Soc. 1959, 4046-4052.
    • (1949) J. Am. Chem. Soc. , vol.71 , pp. 25-28
    • Westheimer, F.H.1    Nicolaides, N.2
  • 69
    • 37049062185 scopus 로고
    • KIEs of 1.9-7 have been reported for cerium, vanadium, cobalt, manganese, and chromium-mediated oxidation via metal-alcoholate complexes: (a) Westheimer, F. H.; Nicolaides, N. J. Am. Chem. Soc. 1949, 71, 25-28. (b) Ardon, M. J. Chem. Soc. 1957, 1811-1815. (c) Litter, J. S.; Waters, W. A. J. Chem. Soc. 1959, 4046-4052.
    • (1957) J. Chem. Soc. , pp. 1811-1815
    • Ardon, M.1
  • 70
    • 0002095610 scopus 로고
    • KIEs of 1.9-7 have been reported for cerium, vanadium, cobalt, manganese, and chromium-mediated oxidation via metal-alcoholate complexes: (a) Westheimer, F. H.; Nicolaides, N. J. Am. Chem. Soc. 1949, 71, 25-28. (b) Ardon, M. J. Chem. Soc. 1957, 1811-1815. (c) Litter, J. S.; Waters, W. A. J. Chem. Soc. 1959, 4046-4052.
    • (1959) J. Chem. Soc. , pp. 4046-4052
    • Litter, J.S.1    Waters, W.A.2
  • 71
    • 17644410133 scopus 로고    scopus 로고
    • note
    • The KIE for the present SET is a secondary one, and it should be much smaller than the primary KIE for hydrogen atom abstraction.
  • 96
    • 0000456170 scopus 로고
    • Trost, B. M., Fleming, I., Pattenden, G., Eds.; Pergamon Press: Oxford
    • Whiting, D. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Pattenden, G., Eds.; Pergamon Press: Oxford, 1991; Vol. 3, pp 659-703.
    • (1991) Comprehensive Organic Synthesis , vol.3 , pp. 659-703
    • Whiting, D.A.1
  • 97
    • 0000613920 scopus 로고
    • Trost, B. M., Ed.; Pergamon Press: Oxford
    • Kochi, J. K. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 7, pp 849-889.
    • (1991) Comprehensive Organic Synthesis , vol.7 , pp. 849-889
    • Kochi, J.K.1
  • 100
    • 17644412406 scopus 로고    scopus 로고
    • note
    • meso-2,3-Diphenylbutane-1,4-diols (15) and its DL-isomer were identified by HPLC analysis using DAICEL CHIRALCEL OD-H (n-hexane/i-PrOH = 90/10, flow rate 0.5 mL/min), respectively: the former gave a single peak, while the latter gave two peaks.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.