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Synthesis 1999; 1999(3): 391-392
DOI: 10.1055/s-1999-3400
short paper
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The Reaction of 4-Substituted Aryl Isocyanates with NaBH4/Trifluoroacetic Acid (TFA)

Kenneth Turnbull* , Douglas M. Krein
  • *Chemistry Department, Wright State University, Dayton, Ohio 45435, USA; Fax +1(9 37)7 75 27 17
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Publikationsdatum:
31. Dezember 1999 (online)

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Treatment of 4-substituted aryl isocyanates (cf. 2a-f) with NaBH4/TFA leads to the corresponding 4-substituted N,N-bis(2,2,2-trifluorethyl)aniline derivatives (3a-d) in excellent yield except where an electron-withdrawing group is present (cf. 2e) or the para-position is open (cf. 2f).

isocyanates - rearrangement - reductive alkylation - trifluoroethylanilines - sodium borohydride

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