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Volumn 72, Issue 6, 2007, Pages 2030-2039

Palladium-mediated N-arylation of heterocyclic diamines: Insights into the origin of an unusual chemoselectivity

Author keywords

[No Author keywords available]

Indexed keywords

BROMOBENZENE; CHEMOSELECTIVITY; HETEROCYCLIC DIAMINES; N-ARYLATION;

EID: 33947218517     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo062301i     Document Type: Article
Times cited : (20)

References (65)
  • 8
    • 0008842650 scopus 로고    scopus 로고
    • Palladium-Catalyzed Amination of Aryl Halides and Sulfonates
    • Ricci, A, Ed, Wiley-VCH: Weinheim, and references therein
    • (c) Hartwig, J. F. Palladium-Catalyzed Amination of Aryl Halides and Sulfonates. In Modern Amination Methods; Ricci, A., Ed.; Wiley-VCH: Weinheim, 2000 and references therein.
    • (2000) Modern Amination Methods
    • Hartwig, J.F.1
  • 12
    • 25444463074 scopus 로고    scopus 로고
    • For recent examples, see: a
    • For recent examples, see: (a) Rao, H.; Fu, H.; Jiang, Y.; Zhao, Y. J. Org. Chem. 2005, 70, 8107-8109.
    • (2005) J. Org. Chem , vol.70 , pp. 8107-8109
    • Rao, H.1    Fu, H.2    Jiang, Y.3    Zhao, Y.4
  • 20
    • 20844435969 scopus 로고    scopus 로고
    • For selected examples, see: a
    • For selected examples, see: (a) Zhang, H.; Cai, Q.; Ma, D. J. Org. Chem. 2005, 70, 5164-5173.
    • (2005) J. Org. Chem , vol.70 , pp. 5164-5173
    • Zhang, H.1    Cai, Q.2    Ma, D.3
  • 25
    • 0032578172 scopus 로고    scopus 로고
    • For Cu-catalyzed N-arylation of cyclohexanediamine, see: d
    • For Cu-catalyzed N-arylation of cyclohexanediamine, see: (d) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 7369-7370.
    • (1998) J. Am. Chem. Soc , vol.120 , pp. 7369-7370
    • Hamann, B.C.1    Hartwig, J.F.2
  • 37
    • 0000403602 scopus 로고
    • Diamine 1d was synthesized in two steps starting from commercially available (+)-lysine according to literature procedures: (a) Bladé-Font, A
    • Diamine 1d was synthesized in two steps starting from commercially available (+)-lysine according to literature procedures: (a) Bladé-Font, A. Tetrahedron Lett. 1980, 21, 2443-2446.
    • (1980) Tetrahedron Lett , vol.21 , pp. 2443-2446
  • 39
    • 33947268305 scopus 로고    scopus 로고
    • No palladium-mediated arylation of 1-benzyl-3-aminopyrrolidine was observed when triphenylphosphine, tricyclohexylphosphine, or diphenylphosphineferrocene was tested as ligand
    • No palladium-mediated arylation of 1-benzyl-3-aminopyrrolidine was observed when triphenylphosphine, tricyclohexylphosphine, or diphenylphosphineferrocene was tested as ligand.
  • 45
    • 33947249917 scopus 로고    scopus 로고
    • 13C NMR spectra (b) and (c) of Figure 3.
    • 13C NMR spectra (b) and (c) of Figure 3.
  • 54
    • 25144450792 scopus 로고    scopus 로고
    • The displacement of one phosphane group of DPPF by a thiol was observed. See
    • The displacement of one phosphane group of DPPF by a thiol was observed. See: Moreau, X.; Campagne, J.-M.; Meyer, G.; Jutand, A. Eur. J. Org. Chem. 2005, 3749-3760.
    • (2005) Eur. J. Org. Chem , pp. 3749-3760
    • Moreau, X.1    Campagne, J.-M.2    Meyer, G.3    Jutand, A.4
  • 63
    • 33947275954 scopus 로고    scopus 로고
    • Although we cannot exclude that the deprotonation of the amine/recoordination of the phosphine is the rate-limiting step, the deprotonation of ammo-palladium complexes similar to B or C occurs at room temperature very rapidly to form arylamines in high yields. See ref 20c
    • Although we cannot exclude that the deprotonation of the amine/recoordination of the phosphine is the rate-limiting step, the deprotonation of ammo-palladium complexes similar to B or C occurs at room temperature very rapidly to form arylamines in high yields. See ref 20c.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.