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Volumn 60, Issue 50, 2004, Pages 11559-11564

Rapid palladium-catalyzed aminations of aryl chlorides with aliphatic amines under temperature-controlled microwave heating

Author keywords

Aryl bromides; Aryl chlorides; Buchwald Hartwig amination; Homogeneous catalysis; Microwave irradiation; Palladium

Indexed keywords

ALIPHATIC AMINE; CHLORIDE ION; PALLADIUM;

EID: 8644243910     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.09.071     Document Type: Article
Times cited : (49)

References (49)
  • 7
    • 0037112673 scopus 로고    scopus 로고
    • For recent reviews containing a chapter on the Buchwald-Hartwig reaction see: (g) A.F. Littke, and G.C. Fu Angew. Chem., Int. Ed. 41 2002 4176 4211
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 4176-4211
    • Littke, A.F.1    Fu, G.C.2
  • 18
    • 0037122141 scopus 로고    scopus 로고
    • Recently, an interesting article appeared dealing with fast (15 min) room temperature Pd-catalyzed aminations of activated and unactivated aryl chlorides using alkyl di-t-butylphosphane ligated palladium(I) dimers. Unfortunately, the scope of this exceptionally fast room-temperature amination chemistry is narrow: (a) J.P. Stambuli, R. Kuwano, and J.F. Hartwig Angew. Chem., Int. Ed. 41 2002 4746 4748
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 4746-4748
    • Stambuli, J.P.1    Kuwano, R.2    Hartwig, J.F.3
  • 19
    • 0034712156 scopus 로고    scopus 로고
    • Although, also other catalysts have been used to perform Buchwald-Hartwig aminations at room temperature the scope is generally broader at higher temperature. Moreover, the reaction times for couplings at room temperature are in the order of hours to one day: (b) J.P. Wolfe, H. Tomori, J.P. Sadighi, J. Yin, and S.L.J. Buchwald J. Org. Chem. 65 2000 1158 1174
    • (2000) J. Org. Chem. , vol.65 , pp. 1158-1174
    • Wolfe, J.P.1    Tomori, H.2    Sadighi, J.P.3    Yin, J.4    Buchwald, S.L.J.5
  • 31
    • 0033549829 scopus 로고    scopus 로고
    • For the amination of aryl chlorides under classical heating using a palladium catalyst based on an electron rich monophosphanylbiaryl ligand see: (a) J.P. Wolfe, and S.L. Buchwald Angew. Chem., Int. Ed. 38 1999 2413 2416
    • (1999) Angew. Chem., Int. Ed. , vol.38 , pp. 2413-2416
    • Wolfe, J.P.1    Buchwald, S.L.2
  • 32
    • 8644257184 scopus 로고    scopus 로고
    • See Ref. 8b.
    • (b) See Ref. 8b.
  • 35
    • 8644276762 scopus 로고    scopus 로고
    • note
    • According to the 'Strem Chemicals' catalogue (2001-2003) 2 g DCPB costs 165 Euro, 2 g DTPB costs 165 Euro and 2 g DCPAB costs 269 Euro.
  • 37
    • 57249108155 scopus 로고    scopus 로고
    • For the intermolecular microwave-assisted palladium-catalyzed amination of aryl bromides see: (a) A. Sharifi, R. Hosseinzadeh, and M. Mirzaei Monatsh. Chem. 133 2002 329 332
    • (2002) Monatsh. Chem. , vol.133 , pp. 329-332
    • Sharifi, A.1    Hosseinzadeh, R.2    Mirzaei, M.3
  • 42
    • 0043009828 scopus 로고    scopus 로고
    • For the intramolecular microwave-assisted palladium-catalyzed amination of aryl bromides see: C.T. Brain, and J.T. Steer J. Org. Chem. 68 2003 6814 6816
    • (2003) J. Org. Chem. , vol.68 , pp. 6814-6816
    • Brain, C.T.1    Steer, J.T.2
  • 45
    • 84862464139 scopus 로고    scopus 로고
    • 2/DTPB at least for 16 h before using it: see Ref. 12d.
    • 2/DTPB at least for 16 h before using it: see Ref. 12d.
  • 48
    • 8644224538 scopus 로고    scopus 로고
    • note
    • In control microwave experiments the amination reactions studied were also executed without the use of Pd-catalyst under otherwise identical reaction conditions. The obtained results clearly indicate that these reactions require the use of transition metal catalyst.
  • 49
    • 8644223670 scopus 로고    scopus 로고
    • note
    • It was not attempted to check whether the studied microwave-assisted aminations were not already finished before 10 minutes. Theoretically, the possibility of a specific microwave effect can therefore not be ruled out. Nevertheless, if there is such a microwave effect, it is surely very small.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.