메뉴 건너뛰기




Volumn 49, Issue 12, 2010, Pages 2185-2189

Copper(I) Phenoxide complexes in the etherification of aryl halides

Author keywords

Copper; Cross coupling; Etherification; Phenoxides

Indexed keywords

ARYL HALIDES; CHELATING LIGANDS; CHEMICAL EQUATIONS; CROSS-COUPLING; CROSS-COUPLINGS; MECHANISTIC PATHWAYS; PHENYL ETHERS;

EID: 77949377447     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.200902245     Document Type: Article
Times cited : (130)

References (38)
  • 18
    • 77949391460 scopus 로고    scopus 로고
    • 6], with p-iodotoluene under the conditions of Scheme 2, and no reaction was observed.
    • 6], with p-iodotoluene under the conditions of Scheme 2, and no reaction was observed.
  • 20
    • 77949359007 scopus 로고    scopus 로고
    • C. P. Andrieux, S. J. M. , D. Zann, New J. Chem. 1984, 8, 107.
    • C. P. Andrieux, S. J. M. , D. Zann, New J. Chem. 1984, 8, 107.
  • 22
    • 77949365808 scopus 로고    scopus 로고
    • As a control, we conducted the reaction of o-(n-propoxy)iodobenzene with 1a in DMSO at 110°C for 12 hours. Consistent with an ortho-alkoxy group leading to low yields from reaction with copper phenoxides, this reaction produced the biaryl ether product in 68% yield and phenyl n-propyl ether from hydrodeiodination in 31 % yield. Reaction with 5 equivalents of the unhindered p-tert-butyl iodobenzene in DMSO at 110°C for 2 hours yielded the ether product in 80 % yield and less than 2 % yield of ferf-butyl benzene derived from hydrodeiodination.
    • As a control, we conducted the reaction of o-(n-propoxy)iodobenzene with 1a in DMSO at 110°C for 12 hours. Consistent with an ortho-alkoxy group leading to low yields from reaction with copper phenoxides, this reaction produced the biaryl ether product in 68% yield and phenyl n-propyl ether from hydrodeiodination in 31 % yield. Reaction with 5 equivalents of the unhindered p-tert-butyl iodobenzene in DMSO at 110°C for 2 hours yielded the ether product in 80 % yield and less than 2 % yield of ferf-butyl benzene derived from hydrodeiodination.
  • 35
    • 35048836256 scopus 로고    scopus 로고
    • T. Gärtner, W. Henze, R. M. Gschwind, J. Am. Chem. Soc. 2007, 130, 11362.
    • T. Gärtner, W. Henze, R. M. Gschwind, J. Am. Chem. Soc. 2007, 130, 11362.
  • 36
    • 50249095782 scopus 로고    scopus 로고
    • E. R. Bartholomew, S. H. Bertz, S. Cope, M. Murphy, C. A. Ogle, J. Am. Chem. Soc. 2008, 130, 11244.
    • E. R. Bartholomew, S. H. Bertz, S. Cope, M. Murphy, C. A. Ogle, J. Am. Chem. Soc. 2008, 130, 11244.
  • 38
    • 77949415489 scopus 로고    scopus 로고
    • CCDC-671252 (1b) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
    • CCDC-671252 (1b) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.