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Volumn 61, Issue 43, 2005, Pages 10338-10348

Microwave-assisted organic synthesis: Scale-up of palladium-catalyzed aminations using single-mode and multi-mode microwave equipment

Author keywords

Aryl chlorides; Buchwald Hartwig amination; Homogeneous catalysis; Microwave irradiation; Multi mode cavity; Palladium; Single mode cavity

Indexed keywords

BENZENE DERIVATIVE; BENZOTRIFLUORIDE; PALLADIUM; SOLVENT; UNCLASSIFIED DRUG;

EID: 25144446828     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.07.105     Document Type: Article
Times cited : (77)

References (60)
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    • For the scale-up of Suzuki reactions in a single-mode microwave of CEM (Discover) using a 50 mL round-bottomed flask see: Leadbetter, N. E.; Marco, M. J. Org. Chem. 2003, 68, 888-892.
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    • For reviews containing a part on recent progress made in palladium-catalyzed amination see: (g) A.F. Littke, and G.C. Fu Angew. Chem., Int. Ed. 41 2002 4176 4211
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    • Littke, A.F.1    Fu, G.C.2
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    • For a review dealing with palladium-catalyzed aminations seen from an industrial point of view see: (j) B. Schlummer, and U. Scholz Adv. Synth. Catal. 346 2004 1599 1626
    • (2004) Adv. Synth. Catal. , vol.346 , pp. 1599-1626
    • Schlummer, B.1    Scholz, U.2
  • 49
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    • For pioneering literature on Buchwald's monodentate phosphine ligands based on a biphenyl backbone see: (a) D.W. Old, J.P. Wolfe, and S.L. Buchwald J. Am. Chem. Soc. 120 1998 9722 9723
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 9722-9723
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    • note
    • initial).
  • 57
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    • note
    • For the amination of 4-chloroanisole with morpholine we also attempted to scale-up with a factor 36 (36 mmol 4-chloroanisole, 43.2 mmol morpholine, 50.4 mmol NaOt-Bu, 36 mL BTF) in the 80 mL vessel of the Discover apparatus. In the same reaction time as for the 1 mmol and 20 mmol experiments (10 min) an isolated yield of 73% of 4-(4-methoxyphenyl)morpholine could be obtained. This is similar to the yield obtained on a 1 mmol scale (78%) but lower than the isolated yield of the 20 mmol experiment (85%).
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    • 2 and DTPB for at least 16 h before using it: D. Zim, and S.L. Buchwald Org. Lett. 5 2003 2413 2415
    • (2003) Org. Lett. , vol.5 , pp. 2413-2415
    • Zim, D.1    Buchwald, S.L.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.