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Volumn 132, Issue 20, 2010, Pages 6900-6901

A new entry of amination reagents for heteroaromatic C-H bonds: Copper-catalyzed direct amination of azoles with chloroamines at room temperature

Author keywords

[No Author keywords available]

Indexed keywords

AMINOAZOLES; C-H BOND; CHLOROAMINES; COPPER CATALYSIS; DIRECT AMINATION; MEDICINAL CHEMISTRY; ROOM TEMPERATURE;

EID: 77952559474     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja101939r     Document Type: Article
Times cited : (375)

References (59)
  • 3
    • 77952571500 scopus 로고    scopus 로고
    • Reviews:
    • Reviews:
  • 7
    • 77952567187 scopus 로고    scopus 로고
    • Selected examples
    • Selected examples
  • 13
    • 77952572274 scopus 로고    scopus 로고
    • Cu-mediated oxidative amination of arylboronic acids also has been developed. Selected works
    • Cu-mediated oxidative amination of arylboronic acids also has been developed. Selected works
  • 33
    • 77952572041 scopus 로고    scopus 로고
    • Recently, the utility of chloroamides and chloroamines as the electrophilic nitrogen sources has been reported
    • Recently, the utility of chloroamides and chloroamines as the electrophilic nitrogen sources has been reported.
  • 37
    • 37049033864 scopus 로고    scopus 로고
    • 2 C-H amination with N -chlorosuccinimide (NCS)
    • 2 C-H amination with N -chlorosuccinimide (NCS). Whitefield, S. R. and Sanford, M. S. J. Am. Chem. Soc. 2007, 129, 15142
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 15142
    • Whitefield, S.R.1    Sanford, M.S.2
  • 38
    • 77952568434 scopus 로고    scopus 로고
    • During the preparation of this manuscript, Hartwig reported the palladium-catalyzed intramolecular direct amination of oxime esters
    • During the preparation of this manuscript, Hartwig reported the palladium-catalyzed intramolecular direct amination of oxime esters
  • 44
    • 77952563542 scopus 로고    scopus 로고
    • See Supporting Information for the detailed optimization studies
    • See Supporting Information for the detailed optimization studies.
  • 45
    • 77952561378 scopus 로고    scopus 로고
    • The direct coupling with the chloroamide such as N -chloroacetanilide was unsuccessful, and the starting materials were recovered unchanged
    • The direct coupling with the chloroamide such as N -chloroacetanilide was unsuccessful, and the starting materials were recovered unchanged.
  • 46
    • 77952559584 scopus 로고    scopus 로고
    • 2-Aminobenzoxazoles in medicinal chemistry
    • 2-Aminobenzoxazoles in medicinal chemistry
  • 49
    • 77952578493 scopus 로고    scopus 로고
    • 2/bpy catalyst and LiHMDS as the base to give the aminated product in 30% yield. The reactions with thiazole and imidazole were unsuccessful
    • 2/bpy catalyst and LiHMDS as the base to give the aminated product in 30% yield. The reactions with thiazole and imidazole were unsuccessful.
  • 51
    • 77952565086 scopus 로고    scopus 로고
    • Base-assisted cupration
    • Base-assisted cupration
  • 56
    • 77952580458 scopus 로고    scopus 로고
    • Regardless of the valency of copper precursors, a small amount of homocoupling product of azole was detected in all cases by GC-MS. The result is suggestive of the existence of Cu species of a higher oxidation state in the catalytic cycle
    • Regardless of the valency of copper precursors, a small amount of homocoupling product of azole was detected in all cases by GC-MS. The result is suggestive of the existence of Cu species of a higher oxidation state in the catalytic cycle.
  • 59
    • 67849106811 scopus 로고    scopus 로고
    • Also see ref 17d. See Supporting Information for the detailed discussion
    • King, A. E., Brunold, T. C., and Stahl, S. S. J. Am. Chem. Soc. 2009, 131, 5044 Also see ref 17d. See Supporting Information for the detailed discussion.
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 5044
    • King, A.E.1    Brunold, T.C.2    Stahl, S.S.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.