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Volumn 16, Issue 18, 2010, Pages 5274-5284

Transition-metal-catalyzed synthesis of hydroxylated arenes

Author keywords

C H activation; Homogeneous catalysis; Hydroxylation; Oxidation; Phenols

Indexed keywords

ARYL HALIDES; C-H ACTIVATION; CATALYZED SYNTHESIS; CROSS-COUPLINGS; HOMOGENEOUS CATALYSIS; REACTION PROTOCOLS;

EID: 77951965391     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201000470     Document Type: Review
Times cited : (194)

References (155)
  • 5
    • 1542582686 scopus 로고
    • (Ed.: S. Patai), Wiley-Interscience, New York
    • a) C. A. Fyfe in The Chemistry of the Hydroxyl Group, Vol.1 (Ed.: S. Patai), Wiley-Interscience, New York, 1971, pp. 83-127;
    • (1971) The Chemistry of the Hydroxyl Group , vol.1 , pp. 83-127
    • Fyfe, C.A.1
  • 10
    • 77951145972 scopus 로고    scopus 로고
    • 2nd ed. (Eds.: M. Beller, C. Bolm), Wiley-VCH, Weinheim
    • b) Transition Metals for Organic Synthesis 2nd ed. (Eds.: M. Beller, C. Bolm), Wiley-VCH, Weinheim, 2004.
    • (2004) Transition Metals for Organic Synthesis
  • 14
    • 33947493717 scopus 로고    scopus 로고
    • d) R. G. Bergman, Nature 2007, 446, 391-394;
    • (2007) Nature , vol.446 , pp. 391-394
    • Bergman, R.G.1
  • 18
    • 67649488045 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2009, 48, 5094-5115;
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 5094-5115
  • 23
    • 72449170089 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2009, 48, 9792-9826;
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 9792-9826
  • 25
    • 0037016398 scopus 로고    scopus 로고
    • Phenol formation with selectivities of 80-97% at benzene conversions of 2-16% are obtained below 250°C
    • Phenol formation with selectivities of 80-97% at benzene conversions of 2-16% are obtained below 250°C: S.-I. Niwa, M. Eswaramoorthy, J. Nair, A. Raj, N. Itoh, H. Shoji, T. Namba, F. Mizukami, Science 2002, 295, 105-107.
    • (2002) Science , vol.295 , pp. 105-107
    • Niwa, S.-I.1    Eswaramoorthy, M.2    Nair, J.3    Raj, A.4    Itoh, N.5    Shoji, H.6    Namba, T.7    Mizukami, F.8
  • 32
    • 77951973802 scopus 로고
    • De Riedel Boston, 1980, pp. 310-312;
    • (1980) , pp. 310-312
    • De Boston, R.1
  • 35
    • 77949792138 scopus 로고    scopus 로고
    • For high-oxidation state Pd catalysis, see: a
    • For high-oxidation state Pd catalysis, see: a) K. Muñiz, Angew. Chem. 2009, 121, 9576-9588;
    • (2009) Angew. Chem. , vol.121 , pp. 9576-9588
    • Muñiz, K.1
  • 36
    • 73249135129 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2009, 48, 9412-9423;
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 9412-9423
  • 55
    • 52949137408 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 5215-5219;
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 5215-5219
  • 56
    • 54849420705 scopus 로고    scopus 로고
    • and references therein.
    • c) R. Giri, J. Q. Yu, J. Am. Chem. Soc. 2008, 130, 14082-1.4083, and references therein.
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 14082-14083
    • Giri, R.1    Yu, J.Q.2
  • 60
    • 4143116053 scopus 로고    scopus 로고
    • For recent reviews, see: a
    • For recent reviews, see: a) S. V. Ley, A. W. Thomas, Angew. Chem. 2003, 115, 5558-5607;
    • (2003) Angew. Chem. , vol.115 , pp. 5558-5607
    • Ley, S.V.1    Thomas, A.W.2
  • 61
    • 0345708168 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2003, 42, 5400-5449;
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 5400-5449
  • 63
    • 36849002980 scopus 로고    scopus 로고
    • For recent advances in Cu-catalyzed oxidations, see
    • For recent advances in Cu-catalyzed oxidations, see: T. Punniyamurthy, L. Rout, Coord. Chem. Rev. 2008, 252, 134-154.
    • (2008) Coord. Chem. Rev. , vol.252 , pp. 134-154
    • Punniyamurthy, T.1    Rout, L.2
  • 74
    • 0033583463 scopus 로고    scopus 로고
    • and references therein.
    • Angew. Chem. Int. Ed. 1999, 38, 1139-1142, and references therein.
    • (1999) Angew. Chem. Int. Ed. , vol.38 , pp. 1139-1142
  • 79
    • 0001146772 scopus 로고    scopus 로고
    • (Eds.: K. M. Kadish, K. M. Smith, R. Guilard), Academic Press, New York
    • b) B. Meunier, A. Robert, G. Pratviel, J. Bernadou, in The Porphyrin Handbook, Vol.4 (Eds.: K. M. Kadish, K. M. Smith, R. Guilard), Academic Press, New York, 1999, p. 119;
    • (1999) The Porphyrin Handbook , vol.4 , pp. 119
    • Meunier, B.1    Robert, A.2    Pratviel, G.3    Bernadou, J.4
  • 95
    • 77951956485 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2000, 59, 4321-4323.
    • (2000) Angew. Chem. Int. Ed. , vol.59 , pp. 4321-4323
  • 104
    • 0242413156 scopus 로고
    • For a previous hydroxylation of a phenoxo ferrie complex to a catecholato complex using MCPBA under noncovalent conditions, see
    • For a previous hydroxylation of a phenoxo ferrie complex to a catecholato complex using MCPBA under noncovalent conditions, see: N. Kitajima, M. Ito, H. Fukui, Y. Morooka, J. Am. Chem. Soc, 1993, 115, 9335-9336.
    • (1993) J. Am. Chem. Soc , vol.115 , pp. 9335-9336
    • Kitajima, N.1    Ito, M.2    Fukui, H.3    Morooka, Y.4
  • 106
    • 0033571369 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 1999, 38, 3391-3393;
    • (1999) Angew. Chem. Int. Ed. , vol.38 , pp. 3391-3393
  • 110
    • 0000644870 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2001, 40, 2168-2171.
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 2168-2171
  • 117
    • 0344871213 scopus 로고    scopus 로고
    • 2] (cod = 1,5-cyclooctdiene) and 4,4′-di-tert-butyl-2,2′-bipyridine together with bis(pinacolato)diboron
    • 2] (cod = 1,5-cyclooctdiene) and 4,4′-di-tert-butyl-2,2′-bipyridine together with bis(pinacolato)diboron: T. Ishiyama, J. Takagi, J. F. Hartwig, N. Miyaura, Angew. Chem. 2002, 114, 3182-3184;
    • (2002) Angew. Chem. , vol.114 , pp. 3182-3184
    • Ishiyama, T.1    Takagi, J.2    Hartwig, J.F.3    Miyaura, N.4
  • 118
    • 0037119304 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2002, 41, 3056-3058.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 3056-3058
  • 119
    • 34248630817 scopus 로고    scopus 로고
    • For recent developments in organic synthesis mediated by rhenium catalyst, see
    • For recent developments in organic synthesis mediated by rhenium catalyst, see: R. Hua, J.-L. Jiang, Curr. Org. Synth. 2007, 4, 151-174.
    • (2007) Curr. Org. Synth. , vol.4 , pp. 151-174
    • Hua, R.1    Jiang, J.-L.2
  • 121
  • 122
    • 34547289191 scopus 로고    scopus 로고
    • For mechanistic considerations in the synthesis of phenol, employing Re-cluster catalysts, see: a
    • For mechanistic considerations in the synthesis of phenol, employing Re-cluster catalysts, see: a) M. Tada, R. Bal, R. Sasaki, Y. Uemura, Y. Inada, S. Tanaka, M, Nomura, Y. Iwasawa, J. Phys. Chem. C 2007, 111, 10095-10104;
    • (2007) J. Phys. Chem. C , vol.111 , pp. 10095-10104
    • Tada, M.1    Bal, R.2    Sasaki, R.3    Uemura, Y.4    Inada, Y.5    Tanaka, S.6    Nomura, M.7    Iwasawa, Y.8
  • 130
  • 132
    • 33746283734 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 4321-4326;
    • (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 4321-4326
  • 136
    • 77951960628 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 7251 7254.
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 72517254
  • 139
    • 24344483855 scopus 로고    scopus 로고
    • For syntheses carried out in water above 200,°C by employing microwave heating see
    • For syntheses carried out in water above 200,°C by employing microwave heating see: B.A. Roberts, C. R. Strauss, Acc. Chem. Res. 2005, 38, 653-661.
    • (2005) Acc. Chem. Res. , vol.38 , pp. 653-661
    • Roberts, B.A.1    Strauss, C.R.2
  • 141
    • 70350590893 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2009, 48, 8725-8728.
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 8725-8728
  • 143
    • 70350586589 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2009, 48, 8729-8732.
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 8729-8732
  • 149
    • 50049109778 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 3317-3321;
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 3317-3321
  • 152
    • 60149095698 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2009, 48, 1364-1367.
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 1364-1367
  • 155
    • 70349783568 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2009, 48, 5586-5587.
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 5586-5587


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.