Nickel-catalyzed amination of aryl chlorides

Journal of the American Chemical Society

Volumn 119, Issue 26, 1997, Pages 6054-6058

  Wolfe, John P ^a   Buchwald, Stephen L ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,10 PHENANTHROLINE; ANILINE DERIVATIVE; CHLORIDE; NICKEL;

AMINATION; ARTICLE; CATALYSIS;

EID: 0030747792     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja964391m     Document Type: Article

References (39)

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20. Previous reports of nickel-catalyzed aryl carbon-nitrogen bond formation consist of a few examples with no isolated yields of products given. The only example of nickel-catalyzed amination of an aryl chloride was the reaction of chlorobenzene with dimethylamine, which required 10 equiv of dimethylamine and only proceeded to 68% conversion after 6 h at 200°C. (a) Cramer, R.; Coulson, D. R. J. Org. Chem. 1975, 40, 2267-2273.
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24. Abbreviations used: dba = dibenzylideneacetone, DPPF= 1,1′-bis(diphenylphosphino)ferrocene, BINAP = 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl, PPFA = N,N-dimethyl-1-[2-(diphenylphosphino)ferrocenyl]ethylamine, PPFE = 1-[2-(diphenylphosphino)ferrocenyl]ethyl methyl ether, DPPP = 1,3-bis(diphenylphosphino)propane, and DPPE = 1,2-bis(diphenylphosphino)ethane.
25. Ratios are not corrected for GC response factors.
26. DPPF is relatively nonpolar, and separation of the excess DPPF from nonpolar aryl amines occasionally required an additional step in the workup to oxidize the phosphine.
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