메뉴 건너뛰기




Volumn 17, Issue 15, 2011, Pages 4104-4108

Hydroxy- and aminophenyl radicals from arenediazonium salts

Author keywords

allylation; arenediazonium salts; biaryls; C C coupling; radical reactions

Indexed keywords

ARENEDIAZONIUM SALTS; BIARYLS; C-C COUPLING; RADICAL REACTIONS; SYNTHETIC APPLICATION; SYNTHETIC ORGANIC CHEMISTRY;

EID: 79953199427     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201003713     Document Type: Article
Times cited : (52)

References (76)
  • 1
    • 0004175758 scopus 로고
    • Wiley-VCH, Weinheim, and references cited therein
    • H. Zollinger, Diazo Chemistry I, Wiley-VCH, Weinheim, 1994, and references cited therein
    • (1994) Diazo Chemistry i
    • Zollinger, H.1
  • 3
    • 79953206771 scopus 로고
    • For a scientific biography of Peter Griess (1829-1888), see
    • For a scientific biography of Peter Griess (1829-1888), see:, O. Krätz, Chem. Unserer Zeit 1976, 10, 42-47.
    • (1976) Chem. Unserer Zeit , vol.10 , pp. 42-47
    • Krätz, O.1
  • 11
    • 79953198078 scopus 로고    scopus 로고
    • For generation and studies of the 2-hydroxyphenyl radical 1 from 2-iodobenzene, see
    • For generation and studies of the 2-hydroxyphenyl radical 1 from 2-iodobenzene, see
  • 15
    • 79953177647 scopus 로고    scopus 로고
    • For characterization and studies of the 4-hydroxyphenyl radical 2, see
    • For characterization and studies of the 4-hydroxyphenyl radical 2, see
  • 18
    • 79953172750 scopus 로고    scopus 로고
    • Reports on (substituted) hydroxyphenyl radicals in relation with DNA strand breakage or natural products
    • Reports on (substituted) hydroxyphenyl radicals in relation with DNA strand breakage or natural products
  • 21
    • 0035805276 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2001, 40, 1704-1705.
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 1704-1705
  • 22
    • 79953222399 scopus 로고    scopus 로고
    • Our optimized procedure for the preparation of 3 and 4 is based on reports by
    • Our optimized procedure for the preparation of 3 and 4 is based on reports by
  • 25
    • 79953171327 scopus 로고    scopus 로고
    • Alternative procedures
    • Alternative procedures
  • 32
    • 79953209506 scopus 로고    scopus 로고
    • see also ref. 12a
    • see also ref. 12a.
  • 36
    • 0008625692 scopus 로고    scopus 로고
    • For Schiemann-type fluorinations with diazonium salts 3 and 4, see
    • For Schiemann-type fluorinations with diazonium salts 3 and 4, see:, M. Sawaguchi, T. Fukuhara, N. Yoneda, J. Fluorine Chem. 1999, 97, 127-133.
    • (1999) J. Fluorine Chem. , vol.97 , pp. 127-133
    • Sawaguchi, M.1    Fukuhara, T.2    Yoneda, N.3
  • 37
    • 79953223901 scopus 로고    scopus 로고
    • For surface modifications, see
    • For surface modifications, see
  • 40
    • 34249104674 scopus 로고    scopus 로고
    • Review on diazonium salts in palladium-catalyzed reactions
    • Review on diazonium salts in palladium-catalyzed reactions:, A. Roglans, A. Pla-Quintana, M. Moreno-Manas, Chem. Rev. 2006, 106, 4622-4643.
    • (2006) Chem. Rev. , vol.106 , pp. 4622-4643
    • Roglans, A.1    Pla-Quintana, A.2    Moreno-Manas, M.3
  • 41
    • 79953190221 scopus 로고    scopus 로고
    • The use of 2- and 4-hydroxyphenyl diazonium salts in Pd-catalyzed cross-coupling reactions has been reported by
    • The use of 2- and 4-hydroxyphenyl diazonium salts in Pd-catalyzed cross-coupling reactions has been reported by
  • 47
    • 56249089672 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 9130-9133
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 9130-9133
  • 58
    • 44449171347 scopus 로고    scopus 로고
    • Aryl radicals can be considered as electrophilic when compared to other carbon-centered radicals. On a general scale including such strong electrophiles as fluorine, they have been classified as moderate to weak nucleophiles
    • Aryl radicals can be considered as electrophilic when compared to other carbon-centered radicals. On a general scale including such strong electrophiles as fluorine, they have been classified as moderate to weak nucleophiles:, F. de Vleeschouwer, V. van Speybroeck, M. Waroquier, P. Geerlings, F. de Proft, Org. Lett. 2007, 9, 2721-2724.
    • (2007) Org. Lett. , vol.9 , pp. 2721-2724
    • De Vleeschouwer, F.1    Van Speybroeck, V.2    Waroquier, M.3    Geerlings, P.4    De Proft, F.5
  • 59
    • 37049163352 scopus 로고
    • For regioselectivity in radical arylations of furans, see
    • For regioselectivity in radical arylations of furans, see:, A. W. Johnson, J. Chem. Soc. 1946, 895-899.
    • (1946) J. Chem. Soc. , pp. 895-899
    • Johnson, A.W.1
  • 60
    • 79953223099 scopus 로고    scopus 로고
    • For regioselectivity in radical arylations of quaternized pyridinium species, see
    • For regioselectivity in radical arylations of quaternized pyridinium species, see
  • 67
    • 79953197735 scopus 로고    scopus 로고
    • No ortho-C-deuterated phenol (2-[D] 5) was formed from the O-deuterated diazonium salt 3 (O-[D] 3), which means that the solvent (dimethyl sulfoxide) acted as preferred hydrogen source. This finding was further supported by the observation that ortho-C-deuterated phenol (2-[D] 5) did occur in reactions with deuterated dimethyl sulfoxide as solvent (see the Supporting Information)
    • No ortho-C-deuterated phenol (2-[D] 5) was formed from the O-deuterated diazonium salt 3 (O-[D] 3), which means that the solvent (dimethyl sulfoxide) acted as preferred hydrogen source. This finding was further supported by the observation that ortho-C-deuterated phenol (2-[D] 5) did occur in reactions with deuterated dimethyl sulfoxide as solvent (see the Supporting Information).
  • 68
    • 2942545129 scopus 로고
    • For rate constants of iodine transfer to aryl radicals, see
    • For rate constants of iodine transfer to aryl radicals, see:, C. Galli, Chem. Rev. 1988, 88, 765-792.
    • (1988) Chem. Rev. , vol.88 , pp. 765-792
    • Galli, C.1
  • 71
    • 79953187413 scopus 로고    scopus 로고
    • 4 as reductant, 2- or 4-hydroxybiphenyl was obtained along with phenol (5) in ratios smaller than 1:20
    • 4 as reductant, 2- or 4-hydroxybiphenyl was obtained along with phenol (5) in ratios smaller than 1:20.
  • 72
    • 79953227197 scopus 로고    scopus 로고
    • 4,4′-Dibromobiphenyl was obtained as by-product potentially arising from the copper-catalyzed cross- coupling reaction (tert-butyl iodide stabilized by Cu)
    • 4,4′-Dibromobiphenyl was obtained as by-product potentially arising from the copper-catalyzed cross- coupling reaction (tert-butyl iodide stabilized by Cu).
  • 73
    • 33846973404 scopus 로고    scopus 로고
    • Reactions of ortho-aminophenyl type radicals have recently been described
    • Reactions of ortho-aminophenyl type radicals have recently been described:, D. A. Androsov, D. C. Neckers, J. Org. Chem. 2007, 72, 1148-1152.
    • (2007) J. Org. Chem. , vol.72 , pp. 1148-1152
    • Androsov, D.A.1    Neckers, D.C.2
  • 76
    • 79953176815 scopus 로고    scopus 로고
    • 3 and benzene
    • 3 and benzene.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.