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Volumn 17, Issue 15, 2011, Pages 4307-4312

A mild oxidative aryl radical addition into alkenes by aerobic oxidation of arylhydrazines

Author keywords

iron; oxygen; peroxides; radical reactions; water

Indexed keywords

AEROBIC OXIDATIONS; ARYLHYDRAZINES; CATALYTIC AMOUNTS; ENVIRONMENTALLY-FRIENDLY; GOOD YIELD; IRON CATALYST; OXYGEN GAS; POTASSIUM FERROCYANIDE; RADICAL ADDITION; RADICAL PRECURSOR; RADICAL REACTIONS; ROOM TEMPERATURE;

EID: 79953205608     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201003060     Document Type: Article
Times cited : (98)

References (130)
  • 1
    • 79953165525 scopus 로고    scopus 로고
    • For reviews, see
    • For reviews, see
  • 2
    • 0004269715 scopus 로고    scopus 로고
    • (Eds.: P. Renaud, M. P. Sibi), Wiley-VCH, Weinheim
    • Radicals in Organic Synthesis (Eds.:, P. Renaud, M. P. Sibi,), Wiley-VCH, Weinheim, 2001
    • (2001) Radicals in Organic Synthesis
  • 4
    • 79953184466 scopus 로고    scopus 로고
    • For recent examples, see
    • For recent examples, see
  • 32
    • 0037201516 scopus 로고    scopus 로고
    • Recently, Wang and co-workers reported arylation of [60]Fullerene using arylhydrazines and oxidant, see
    • A. S. Demir, Ö. Reis, M. Emrullahoǧlu, Tetrahedron 2002, 58, 8055. Recently, Wang and co-workers reported arylation of [60]Fullerene using arylhydrazines and oxidant, see
    • (2002) Tetrahedron , vol.58 , pp. 8055
    • Demir, A.S.1    Reis, Ö.2    Emrullahoǧlu, M.3
  • 37
    • 79953213847 scopus 로고    scopus 로고
    • For reviews on Meerwein arylation, see
    • For reviews on Meerwein arylation, see
  • 38
    • 0038800178 scopus 로고    scopus 로고
    • in (Eds.: P. Renaud, M. P. Sibi), Wiley-VCH, Weinheim, pp
    • J. A. Murphy, in Radicals in Organic Synthesis, Vol. 1 (Eds.:, P. Renaud, M. P. Sibi,), Wiley-VCH, Weinheim, 2001, pp. 298-315
    • (2001) Radicals in Organic Synthesis, Vol. 1 , pp. 298-315
    • Murphy, J.A.1
  • 40
    • 79953201350 scopus 로고    scopus 로고
    • For reviews, see
    • For reviews, see
  • 50
    • 79953206425 scopus 로고    scopus 로고
    • For examples of iron-mediated radical reactions, see
    • For examples of iron-mediated radical reactions, see
  • 65
    • 79953228686 scopus 로고    scopus 로고
    • 2, see
    • 2, see
  • 69
    • 29844446598 scopus 로고    scopus 로고
    • For the synthesis of alcohols by air-assisted addition of Grignard reagents to alkenes, see
    • For the synthesis of alcohols by air-assisted addition of Grignard reagents to alkenes, see:, Y. Nobe, K. Arayama, H. Urabe, J. Am. Chem. Soc. 2005, 127, 18006.
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 18006
    • Nobe, Y.1    Arayama, K.2    Urabe, H.3
  • 70
    • 79953220298 scopus 로고    scopus 로고
    • For the recent examples of oxyarylation, see
    • For the recent examples of oxyarylation, see
  • 78
    • 79953189866 scopus 로고    scopus 로고
    • Under these conditions, acetophenone and benzyl alcohol were isolated. It was assumed that these compounds were produced by a 1,2-alkyl shift onto the oxygen atom of hydroperoxide 3 a
    • Under these conditions, acetophenone and benzyl alcohol were isolated. It was assumed that these compounds were produced by a 1,2-alkyl shift onto the oxygen atom of hydroperoxide 3 a.
  • 79
    • 79953178058 scopus 로고    scopus 로고
    • Mukaiyama and co-workers have reported cobalt-catalyzed hydroperoxidation of alkenes, see
    • Mukaiyama and co-workers have reported cobalt-catalyzed hydroperoxidation of alkenes, see
  • 80
    • 0002993450 scopus 로고
    • For recent examples of the synthesis of peroxide compounds, see
    • T. Mukaiyama, T. Yamada, Bull. Chem. Soc. Jpn. 1995, 68, 17. For recent examples of the synthesis of peroxide compounds, see
    • (1995) Bull. Chem. Soc. Jpn. , vol.68 , pp. 17
    • Mukaiyama, T.1    Yamada, T.2
  • 89
    • 79953189196 scopus 로고    scopus 로고
    • 4-) is positive (E=+0.36 V)
    • 4-) is positive (E=+0.36 V).
  • 90
    • 79953206083 scopus 로고    scopus 로고
    • 6] to give diazene compounds has been reported, see
    • 6] to give diazene compounds has been reported, see
  • 94
    • 79953184465 scopus 로고    scopus 로고
    • For the oxidation of phenyldiazene, see
    • For the oxidation of phenyldiazene, see
  • 97
    • 79953178756 scopus 로고    scopus 로고
    • Oxyhemoglobin-catalyzed aerobic oxidation of phenylhydrazine has been reported. In this reaction, it is presumed that oxyhemoglobin, which is an iron-oxygen complex, accelerates the first single-electron oxidation of phenylhydrazine, see
    • Oxyhemoglobin-catalyzed aerobic oxidation of phenylhydrazine has been reported. In this reaction, it is presumed that oxyhemoglobin, which is an iron-oxygen complex, accelerates the first single-electron oxidation of phenylhydrazine, see
  • 100
    • 0000423906 scopus 로고    scopus 로고
    • Oxidation of ferrocyanide to ferricyanide by peroxy radical has been reported, see
    • Oxidation of ferrocyanide to ferricyanide by peroxy radical has been reported, see:, G. I. Khaikin, Z. B. Alfassi, R. E. Huie, P. Nera, J. Phys. Chem. 1996, 100, 7072.
    • (1996) J. Phys. Chem. , vol.100 , pp. 7072
    • Khaikin, G.I.1    Alfassi, Z.B.2    Huie, R.E.3    Nera, P.4
  • 101
    • 79953227865 scopus 로고    scopus 로고
    • For examples of the significant effects of water as a solvent, see
    • For examples of the significant effects of water as a solvent, see
  • 105
    • 34548525558 scopus 로고    scopus 로고
    • The difference between homogeneous "in water" and heterogeneous "in the presence of water" has been discussed, see
    • I. Vilotijevic, T. F. Jamison, Science 2007, 317, 1189; The difference between homogeneous "in water" and heterogeneous "in the presence of water" has been discussed, see
    • (2007) Science , vol.317 , pp. 1189
    • Vilotijevic, I.1    Jamison, T.F.2
  • 109
    • 33845788846 scopus 로고    scopus 로고
    • An objection against exaggerated claims for some advantages in using water has also been suggested, see
    • Angew. Chem. Int. Ed. 2006, 45, 8103. An objection against exaggerated claims for some advantages in using water has also been suggested, see
    • (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 8103
  • 112
    • 79953225692 scopus 로고    scopus 로고
    • Although the effect of the substituent groups of arylhydrazines is unclear in the present reaction, it is known that the oxidation potential increases with the electron deficiency of an aromatic ring, see
    • Although the effect of the substituent groups of arylhydrazines is unclear in the present reaction, it is known that the oxidation potential increases with the electron deficiency of an aromatic ring, see
  • 115
    • 0000782249 scopus 로고    scopus 로고
    • For radical clocks, see: in (Eds.: P. Renaud, M. P. Sibi), Wiley-VCH, Weinheim, pp. . In the reversible ring opening-closing process of a cyclopropylmethyl radical, an α-cyclopropylbenzyl radical such as a radical generated from compound 1 h is thermodynamically favored. On the other hand, a 2-phenylcyclopropylmethyl radical, such as radical A, rapidly undergoes a ring-opening reaction to give a thermodynamically stable benzyl radical such as radical B
    • For radical clocks, see:, M. Newcomb, in Radicals in Organic Synthesis, Vol. 2 (Eds.:, P. Renaud, M. P. Sibi,), Wiley-VCH, Weinheim, 2001, pp. 317-336. In the reversible ring opening-closing process of a cyclopropylmethyl radical, an α-cyclopropylbenzyl radical such as a radical generated from compound 1 h is thermodynamically favored. On the other hand, a 2-phenylcyclopropylmethyl radical, such as radical A, rapidly undergoes a ring-opening reaction to give a thermodynamically stable benzyl radical such as radical B.
    • (2001) Radicals in Organic Synthesis, Vol. 2 , pp. 317-336
    • Newcomb, M.1
  • 116
    • 79953210926 scopus 로고    scopus 로고
    • For rare examples of stereoselective hydroxylation by molecular oxygen, see
    • For rare examples of stereoselective hydroxylation by molecular oxygen, see


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.