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Volumn 61, Issue 25, 2005, Pages 5955-6008

Palladium-catalysed reactions of alcohols. Part C: Formation of ether linkages

Author keywords

3 Allylpalladium; Alcohols; Etherification; Heterocyclisation; Oxypalladation; Palladium

Indexed keywords

ALCOHOL DERIVATIVE; ALKADIENE; ALKENE DERIVATIVE; EPOXIDE; ETHER; PALLADIUM; SILANE DERIVATIVE;

EID: 20444497757     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.04.002     Document Type: Review
Times cited : (163)

References (481)
  • 1
    • 0038106766 scopus 로고    scopus 로고
    • Part A: Palladium-catalysed oxidation of primary and secondary alcohols
    • J. Muzart Part A: Palladium-catalysed oxidation of primary and secondary alcohols Tetrahedron 59 2003 5789 5816
    • (2003) Tetrahedron , vol.59 , pp. 5789-5816
    • Muzart, J.1
  • 2
    • 16244407390 scopus 로고    scopus 로고
    • Part B: Palladium-catalysed reactions of alcohols: formation of C-C and C-N bonds from unsaturated alcohols
    • J. Muzart Part B: Palladium-catalysed reactions of alcohols: formation of C-C and C-N bonds from unsaturated alcohols Tetrahedron 61 2005 4179 4212
    • (2005) Tetrahedron , vol.61 , pp. 4179-4212
    • Muzart, J.1
  • 13
    • 0141682457 scopus 로고    scopus 로고
    • 1-Methoxy-1,3-diphenylpropene can be obtained from 1-acetoxy-1,3- diphenylpropene and aqueous methanol even in the absence of a metal-catalyst: C. Chevrin, J. Le Bras, F. Hénin, and J. Muzart Tetrahedron Lett. 44 2003 8099 8102
    • (2003) Tetrahedron Lett. , vol.44 , pp. 8099-8102
    • Chevrin, C.1    Le Bras, J.2    Hénin, F.3    Muzart, J.4
  • 31
    • 0038627629 scopus 로고    scopus 로고
    • 3- allylpalladium, water could mediate the palladium-catalysed 'hydrolysis' of allyl tert-butyl carbonate through the formation of allyl hydrogen carbonate, leading finally to allyl alcohol and carbon dioxide: (a) B. Lüssem, and H.-J. Gais J. Am. Chem. Soc. 125 2003 6066 6067
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 6066-6067
    • Lüssem, B.1    Gais, H.-J.2
  • 36
    • 20444454026 scopus 로고    scopus 로고
    • Chem. Abstr. 141, 314494
    • Chem. Abstr. , vol.141 , pp. 314494
  • 43
    • 20444501315 scopus 로고
    • Hayashi, T.; Uozumi, Y.; Tanahashi, A.; Kyoi, T., Jpn. Kokai Tokkyo Koho JP 05,255,285, 1993;
    • (b) Hayashi, T.; Uozumi, Y.; Tanahashi, A.; Kyoi, T., Jpn. Kokai Tokkyo Koho JP 05,255,285, 1993; Chem. Abstr. 1994, 120, 164205.
    • (1994) Chem. Abstr. , vol.120 , pp. 164205
  • 55
  • 67
    • 20444458660 scopus 로고    scopus 로고
    • Godleski, S. A. PCT Int. Appl. WO 89 02,883.
    • Godleski, S. A. PCT Int. Appl. WO 89 02,883.
  • 68
    • 20444498193 scopus 로고
    • Chem. Abstr. 111 1989 173607
    • (1989) Chem. Abstr. , vol.111 , pp. 173607
  • 81
    • 0001208668 scopus 로고
    • Bäckvall et al. have effectively shown the coordination of quinones to palladium species: (a) J.-E. Bäckvall, and A. Gogoll Tetrahedron Lett. 29 1988 2243 2246
    • (1988) Tetrahedron Lett. , vol.29 , pp. 2243-2246
    • Bäckvall, J.-E.1    Gogoll, A.2
  • 98
    • 0000143391 scopus 로고
    • G. Wilkinson F.G.A. Stone E.W. Abel Elsevier Oxford
    • J.M. Takacs G. Wilkinson F.G.A. Stone E.W. Abel Comprehensive organometallic chemistry II Vol. 12 1995 Elsevier Oxford 785 796
    • (1995) Comprehensive organometallic chemistry II , vol.12 , pp. 785-796
    • Takacs, J.M.1
  • 99
    • 20444478266 scopus 로고    scopus 로고
    • (a) Jacobsen, G. B.; Pelt, H. L.; Schaart, B. J., PCT Int. Appl. WO 9109822
    • (a) Jacobsen, G. B.; Pelt, H. L.; Schaart, B. J., PCT Int. Appl. WO 9109822; Chem. Abstr. 115, 158514.
    • Chem. Abstr. , vol.115 , pp. 158514
  • 100
    • 0004006465 scopus 로고
    • National Distillers and Chemical Corp. Jpn. Kokai Tokkyo Koho JP 62063538, 1987;
    • (b) National Distillers and Chemical Corp. Jpn. Kokai Tokkyo Koho JP 62063538, 1987; Chem. Abstr. 1987, 533904.
    • (1987) Chem. Abstr. , pp. 533904
  • 101
    • 20444457896 scopus 로고    scopus 로고
    • Ishino, H.; Iwasaki, H. PCT Int. Appl. WO 65,006, 2004;
    • (c) Ishino, H.; Iwasaki, H. PCT Int. Appl. WO 65,006, 2004; Chem. Abstr. 141, 156682.
    • Chem. Abstr. , vol.141 , pp. 156682
  • 108
    • 20444442710 scopus 로고    scopus 로고
    • Hill, K.; Axt, S. D.; Weese, K. J., PCT Int. Appl. WO 9302032;
    • Hill, K.; Axt, S. D.; Weese, K. J., PCT Int. Appl. WO 9302032; Chem. Abstr. 119, 94948.
    • Chem. Abstr. , vol.119 , pp. 94948
  • 109
    • 0347429171 scopus 로고
    • Gruber, B.; Weese, K. J.; Hoagland, S. M.; Mueller, H.-P.; Hill, K.; Behr, A. PCT Int. Appl. WO 13531, 1990;
    • (a) Gruber, B.; Weese, K. J.; Hoagland, S. M.; Mueller, H.-P.; Hill, K.; Behr, A. PCT Int. Appl. WO 13531, 1990; Chem. Abstr. 1991, 115, 137003.
    • (1991) Chem. Abstr. , vol.115 , pp. 137003
  • 110
    • 1242271904 scopus 로고
    • Hill, K.; Weese, K. J., Ger. Offen. DE 92-4242467;
    • (b) Hill, K.; Weese, K. J., Ger. Offen. DE 92-4242467; Chem. Abstr. 1994, 120, 301648.
    • (1994) Chem. Abstr. , vol.120 , pp. 301648
  • 111
    • 20444500876 scopus 로고    scopus 로고
    • Pennequin, I.; Mortreux, A.; Petit, F.; Mentech, J.; Thiriet, B., Brev. Fr., FR 92 08116;
    • (c) Pennequin, I.; Mortreux, A.; Petit, F.; Mentech, J.; Thiriet, B., Brev. Fr., FR 92 08116; Chem. Abstr. 121, 205887.
    • Chem. Abstr. , vol.121 , pp. 205887
  • 112
    • 4544384541 scopus 로고    scopus 로고
    • Muzart, J.; Hénin, F.; Estrine, B.; Bouquillon, S. 2001, Fr Patent 0116363; PCT Int. Appl. WO 03 053987;
    • (d) Muzart, J.; Hénin, F.; Estrine, B.; Bouquillon, S. 2001, Fr Patent 0116363; PCT Int. Appl. WO 03 053987; Chem Abstr. 2003, 139, 54601.
    • (2003) Chem Abstr. , vol.139 , pp. 54601
  • 141
    • 26744439073 scopus 로고
    • Kuntz, E. U.S. US 4,142,060, 1978;
    • Kuntz, E. U.S. US 4,142,060, 1978; Chem. Abstr. 1978, 88, 152026.
    • (1978) Chem. Abstr. , vol.88 , pp. 152026
  • 142
    • 20444507534 scopus 로고    scopus 로고
    • PhD Thesis, Reims
    • Estrine, B., PhD Thesis, Reims, 2002.
    • (2002)
    • Estrine, B.1
  • 149
    • 20444505978 scopus 로고    scopus 로고
    • Watanabe, K.; Ogoshi, N. Jpn. Kokai Tokkyo Koho JP, 323369, 2004;
    • (a) Watanabe, K.; Ogoshi, N. Jpn. Kokai Tokkyo Koho JP, 323369, 2004; Chem. Abstr. 141, 410639.
    • Chem. Abstr. , vol.141 , pp. 410639
  • 170
    • 20444478265 scopus 로고    scopus 로고
    • note
    • 129
  • 201
    • 0021481894 scopus 로고
    • Methyl ethers have been obtained as side products of the Pd-catalysed hydrocarbomethoxylation of 2-phenylpropene and acenaphthylene: (a) T. Hayashi, M. Tanaka, and I. Ogata J. Mol. Catal. 26 1984 17 30
    • (1984) J. Mol. Catal. , vol.26 , pp. 17-30
    • Hayashi, T.1    Tanaka, M.2    Ogata, I.3
  • 204
    • 2942568460 scopus 로고    scopus 로고
    • Asymmetric Michael reactions catalysed by chiral palladium complexes, leading to C-C and C-N bonds with up to 83 and 98% ee, respectively, have been, however, reported: (a) K. Takenaka, and Y. Uozumi Org. Lett. 6 2004 1833 1835
    • (2004) Org. Lett. , vol.6 , pp. 1833-1835
    • Takenaka, K.1    Uozumi, Y.2
  • 212
    • 20444451194 scopus 로고    scopus 로고
    • note
    • 167
  • 255
    • 20444502904 scopus 로고    scopus 로고
    • Personal communication April, 15
    • 4 is to act as a base: Gouverneur, V. Personal communication April, 15, 2004.
    • (2004)
    • Gouverneur, V.1
  • 256
    • 20444450090 scopus 로고    scopus 로고
    • 176
    • 176
  • 261
  • 274
    • 0009860332 scopus 로고    scopus 로고
    • The formation of the ketal from the hydroxyalkyl vinyl ether intermediate could be mediated by acid rather than palladium: (a) M. Larhed, and A. Hallberg J. Org. Chem. 62 1997 7858 7862
    • (1997) J. Org. Chem. , vol.62 , pp. 7858-7862
    • Larhed, M.1    Hallberg, A.2
  • 291
    • 20444475692 scopus 로고    scopus 로고
    • Hayden, P. Brit. Pat. GB 1119657, 1968;
    • (a) Hayden, P. Brit. Pat. GB 1119657, 1968; Chem. Abstr. 93, 149792;
    • Chem. Abstr. , vol.93 , pp. 149792
  • 292
    • 20444496008 scopus 로고    scopus 로고
    • Takagi, K.; Motohashi, T. Jpn. Kokai Tokkyo Koho JP 72-87803, 1974;
    • (b) Takagi, K.; Motohashi, T. Jpn. Kokai Tokkyo Koho JP 72-87803, 1974; Chem. Abstr. 81, 119951.
    • Chem. Abstr. , vol.81 , pp. 119951
  • 301
    • 20444432257 scopus 로고
    • Takagi, K., Motobashi, C. Jpn. Tokkyo Koho JP 72-87802;
    • Takagi, K., Motobashi, C. Jpn. Tokkyo Koho JP 72-87802; Chem. Abstr., 1980, 93, 149792.
    • (1980) Chem. Abstr. , vol.93 , pp. 149792
  • 348
    • 0001550524 scopus 로고
    • 2 are sometimes used for cyclisations leading to dihydropyrans: (a) M. Riediker, and J.K. Schwartz J. Am. Chem. Soc. 104 1982 5842 5844
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 5842-5844
    • Riediker, M.1    Schwartz, J.K.2
  • 364
    • 20444491145 scopus 로고
    • Chem. Abstr. 120 1994 163831
    • (1994) Chem. Abstr. , vol.120 , pp. 163831
  • 392
    • 20444473438 scopus 로고    scopus 로고
    • note
    • 314 the substitution of aryl bromides occurs, in some cases, in DMF without catalyst, but lower yields are generally obtained.
  • 404
    • 20444459046 scopus 로고    scopus 로고
    • Chem. Abstr. 135: 210769.
    • Chem. Abstr. , vol.135 , pp. 210769
  • 405
    • 20444460236 scopus 로고    scopus 로고
    • Dzhemilev, U. M; Khusnutdinov, R. I.; Shchadneva, N. A.; Malikov, A. I. Russian Patent RU 2145593 C1, 2000;
    • (b) Dzhemilev, U. M; Khusnutdinov, R. I.; Shchadneva, N. A.; Malikov, A. I. Russian Patent RU 2145593 C1, 2000; Chem. Abstr. 135, 210774.
    • Chem. Abstr. , vol.135 , pp. 210774
  • 416
    • 20444506753 scopus 로고    scopus 로고
    • Fujii, Y.; Okutsu, T.; Furugaki, H.; Kita, K., Jpn. Kokai Tokkyo Koho JP 09 67,288, 1997;
    • (a) Fujii, Y.; Okutsu, T.; Furugaki, H.; Kita, K., Jpn. Kokai Tokkyo Koho JP 09 67,288, 1997; Chem. Abstr. 126, 293089;
    • Chem. Abstr. , vol.126 , pp. 293089
  • 417
    • 20444503874 scopus 로고    scopus 로고
    • Fujii, Y.; Uno, M.; Tamura, H.; Kita, K. Jpn. Kokai Tokkyo Koho JP 09 316,017, 1997;
    • (b) Fujii, Y.; Uno, M.; Tamura, H.; Kita, K. Jpn. Kokai Tokkyo Koho JP 09 316,017, 1997; Chem. Abstr. 128, 75107.
    • Chem. Abstr. , vol.128 , pp. 75107
  • 419
    • 20444463982 scopus 로고    scopus 로고
    • Fujii, Y.; Furugaki, H.; Kita, K. Jpn. Kokai Tokkyo Koho JP 09 67,289;
    • Fujii, Y.; Furugaki, H.; Kita, K. Jpn. Kokai Tokkyo Koho JP 09 67,289; Chem. Abstr. 1997, 126, 293090.
    • (1997) Chem. Abstr. , vol.126 , pp. 293090
  • 420
    • 20444473085 scopus 로고    scopus 로고
    • Fujii, Y.; Furugaki, H.; Kita, K. Jpn. Kokai Tokkyo Koho JP, 09 67,290;
    • Fujii, Y.; Furugaki, H.; Kita, K. Jpn. Kokai Tokkyo Koho JP, 09 67,290; Chem. Abstr. 1997, 126, 293091.
    • (1997) Chem. Abstr. , vol.126 , pp. 293091
  • 421
    • 20444466438 scopus 로고    scopus 로고
    • note
    • 333
  • 438
    • 0011394770 scopus 로고
    • For the introduction of this expression and its use, see: (a) J.E. Berson, and M.R. Willcott J. Org. Chem. 30 1965 3569 3572
    • (1965) J. Org. Chem. , vol.30 , pp. 3569-3572
    • Berson, J.E.1    Willcott, M.R.2
  • 444
    • 0033964272 scopus 로고    scopus 로고
    • These results of the Kato team contrast with those of Okumoto et al., who observed only a reaction at the level of the triple bond leading to γ-acetoxy-β-methoxy-α,β-unsaturated esters: H. Okumoto, S. Nishihara, H. Nakagawa, and A. Suzuki Synlett 2000 217 218
    • (2000) Synlett , pp. 217-218
    • Okumoto, H.1    Nishihara, S.2    Nakagawa, H.3    Suzuki, A.4
  • 449
    • 20444497280 scopus 로고    scopus 로고
    • note
    • 160
  • 454
    • 20444454988 scopus 로고
    • Kerby, M. C.; Vaughan, D. E. W. U.S. US 5,364,980, 1994;
    • (a) Kerby, M. C.; Vaughan, D. E. W. U.S. US 5,364,980, 1994; Chem. Abstr. 1995, 122, 55587.
    • (1995) Chem. Abstr. , vol.122 , pp. 55587
  • 455
    • 20444501312 scopus 로고
    • Knifton, J. F.; Dai, P. S. E. U.S. US 5,364,981, 1994.
    • (b) Knifton, J. F.; Dai, P. S. E. U.S. US 5,364,981, 1994. Chem. Abstr. 1995, 122, 55588.
    • (1995) Chem. Abstr. , vol.122 , pp. 55588
  • 478
    • 20444491530 scopus 로고    scopus 로고
    • Personal communication January 10
    • Tenaglia, A. Personal communication January 10, 2005.
    • (2005)
    • Tenaglia, A.1


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