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Volumn 131, Issue 31, 2009, Pages 11049-11061

Palladium-catalyzed coupling of ammonia with aryl chlorides, bromides, iodides, and sulfonates: A general method for the preparation of primary arylamines

Author keywords

[No Author keywords available]

Indexed keywords

ACID CHLORIDES; ACTIVE CATALYST; ARYL AMINES; ARYL BROMIDES; ARYL CHLORIDE; ARYL ELECTROPHILES; ARYL SULFONATES; CARBONYL COMPOUNDS; CATALYST LOADINGS; CATALYST PRECURSORS; CATALYZED COUPLING; FASTER RATES; GENERAL METHOD; HIGH YIELD; HIGHER YIELD; LOW CONCENTRATIONS; MECHANISTIC STUDIES; ONE-POT SYNTHESIS; SELECTIVE CATALYSTS;

EID: 68249154736     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja903049z     Document Type: Article
Times cited : (282)

References (65)
  • 12
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    • After the submission of our paper, this paper on the coupling of aryl bromides with ammonia catalyzed by copper complexes of carbene ligands was retracted and deleted from the journal website
    • Ntaganda, R.; Dhudshia, B.; Macdonald, C. L. B.; Thadani, A. N. Chem. Commun. 2008, 6200-6202. After the submission of our paper, this paper on the coupling of aryl bromides with ammonia catalyzed by copper complexes of carbene ligands was retracted and deleted from the journal website.
    • (2008) Chem. Commun , pp. 6200-6202
    • Ntaganda, R.1    Dhudshia, B.2    Macdonald, C.L.B.3    Thadani, A.N.4
  • 25
    • 68249133189 scopus 로고    scopus 로고
    • Soon after the submission of this article, a report on ligandless copper-catalyzed coupling of aryl bromides and chlorides with ammonia in water was published Xu, H. Wolf, C. Chem. Commun. 2009, 3035-3037. In our hands, the reaction of 2-bromotoluene with aqueous ammonia by the published protocols using various sources of copper iodide, open or closed vessels, and reaction vessels with varying headspaces afforded less than 10% of ortho-toluidine. Thus, we abandonded studies to compare our system to this one
    • Soon after the submission of this article, a report on ligandless copper-catalyzed coupling of aryl bromides and chlorides with ammonia in water was published Xu, H. Wolf, C. Chem. Commun. 2009, 3035-3037. In our hands, the reaction of 2-bromotoluene with aqueous ammonia by the published protocols using various sources of copper iodide, open or closed vessels, and reaction vessels with varying headspaces afforded less than 10% of ortho-toluidine. Thus, we abandonded studies to compare our system to this one.
  • 26
    • 67249109649 scopus 로고    scopus 로고
    • While this work was under review, Ma and co-workers reported the coupling of 2-bromoanisole and 2-bromotoluene with ammonia in water in the presence of 20% CuI and 40 mol, of 4-hydroxy-Lproline to give 81 and 55% yields of the primary arylamines, respectively: Jiang, L, Lu, X, Zhang, H, Jiang, Y, Ma, D. J. Org. Chem. 2009, 74, 4542-4546. In contrast to the work with ligandless catalysts in ref 25, we have obtained yields (69 and 60, respectively) that are close to those published, but these yields are still lower than those in the current work with palladium catalysts
    • While this work was under review, Ma and co-workers reported the coupling of 2-bromoanisole and 2-bromotoluene with ammonia in water in the presence of 20% CuI and 40 mol % of 4-hydroxy-Lproline to give 81 and 55% yields of the primary arylamines, respectively: Jiang, L.; Lu, X.; Zhang, H.; Jiang, Y.; Ma, D. J. Org. Chem. 2009, 74, 4542-4546. In contrast to the work with ligandless catalysts in ref 25, we have obtained yields (69 and 60%, respectively) that are close to those published, but these yields are still lower than those in the current work with palladium catalysts.
  • 42
    • 69949162827 scopus 로고    scopus 로고
    • For recent reports on efficient couplings of aryl iodides, see ref 19 and the following reference: Fors, B. P, Davis, N. R, Buchwald, S. L. J. Am. Chem. Soc. 2009, 131, 5766-5768
    • For recent reports on efficient couplings of aryl iodides, see ref 19 and the following reference: Fors, B. P.; Davis, N. R.; Buchwald, S. L. J. Am. Chem. Soc. 2009, 131, 5766-5768.
  • 51
    • 0004136578 scopus 로고    scopus 로고
    • Ricci, A, Ed, Wiley-VCH: Weinheim, Germany
    • Hartwig, J. F. In Modern Amination Methods; Ricci, A., Ed.; Wiley-VCH: Weinheim, Germany, 2000.
    • (2000) Modern Amination Methods
    • Hartwig, J.F.1
  • 52
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    • De Meijere, A, Diederich, F, Eds, Wiley-VCH: Weinheim, Germany
    • Jiang, L.; Buchwald, S. L. In Metal-Catalyzed Cross-Coupling Reactions; De Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany, 2004; Vol. 2, p 699.
    • (2004) Metal-Catalyzed Cross-Coupling Reactions , vol.2 , pp. 699
    • Jiang, L.1    Buchwald, S.L.2
  • 64
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    • a value obtained from ionization of liquid ammonia: Coulter, L. V.; Sinclair, J. R.; Cole, A. G.; Roper, G. C. J. Am. Chem. Soc. 1959, 81, 2986-2989.
    • a value obtained from ionization of liquid ammonia: Coulter, L. V.; Sinclair, J. R.; Cole, A. G.; Roper, G. C. J. Am. Chem. Soc. 1959, 81, 2986-2989.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.