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Volumn 68, Issue 25, 2003, Pages 9563-9573

Palladium-Catalyzed Amination of Aryl Nonaflates

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LIGANDS;

EID: 0345529047     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034962a     Document Type: Article
Times cited : (118)

References (81)
  • 20
    • 0344990539 scopus 로고    scopus 로고
    • note
    • Aryl nonaflates are prepared with perfluoro-1-butanesulfonyl fluoride (Aldrich Chem. Co.), which is comparable in price to triflic anhydride (Aldrich Chem. Co.).
  • 40
    • 0033948093 scopus 로고    scopus 로고
    • Amination reactions utilizing sulfoximines and aryl nonaflates have been reported: Bolm, C.; Hildebrand, J. P.; Rudolph, J. Synthesis 2000, 7, 911.
    • (2000) Synthesis , vol.7 , pp. 911
    • Bolm, C.1    Hildebrand, J.P.2    Rudolph, J.3
  • 50
    • 0344127940 scopus 로고    scopus 로고
    • note
    • 4 as the base led preferentially to amination at bromine along with the diamination products. No reaction was observed with -hexylamine.
  • 51
    • 0344559479 scopus 로고    scopus 로고
    • note
    • DPEphos = bis[2-(diphenylphosphino)phenyl] ether; dppf= 1,1′bis(diphenylphosphino)ferrocene.
  • 52
    • 0345421622 scopus 로고    scopus 로고
    • note
    • This is the same behavior observed with the corresponding aryl triflate (see ref 2e).
  • 53
    • 0344559480 scopus 로고    scopus 로고
    • note
    • 4 as base did not proceed beyond 65% conversion.
  • 54
    • 0344127939 scopus 로고    scopus 로고
    • note
    • Cleavage of the nonaflate was observed in the presence of amine and alkoxide in the absence of Pd. This side reaction had also been observed with the corresponding triflates (see ref 2f).
  • 55
    • 0345030827 scopus 로고
    • These halide additives are often necessary to obtain high yields of coupled products with aryl triflates in Stille reactions: (a) Echavarren, A. M. ; Stille, J. K. J. Am. Chem. Soc. 1987, 109, 5478.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 5478
    • Echavarren, A.M.1    Stille, J.K.2
  • 57
    • 0029044538 scopus 로고
    • It has been reported that the addition of halides inhibits the amination of aryl halides: (a) Louie, J.; Hartwig, J. F. Tetrdhedron Lett. 1995, 36, 3609.
    • (1995) Tetrdhedron Lett. , vol.36 , pp. 3609
    • Louie, J.1    Hartwig, J.F.2
  • 59
    • 0345421621 scopus 로고    scopus 로고
    • note
    • In these reactions only trace amounts of phenol or diamination products were detected by GC analysis.
  • 60
    • 0037024173 scopus 로고    scopus 로고
    • For recent Pd-catalyzed reactions where an aryl halide (Br, Cl) reacts in preference to an aryl triflate, see: (a) Littke, A. F.; Schwarz, L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 6343.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 6343
    • Littke, A.F.1    Schwarz, L.2    Fu, G.C.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.