404-27-3Relevant articles and documents
The reaction of 4-substituted aryl isocyanates with NaBH4/trifluoroacetic acid (TFA)
Turnbull, Kenneth,Krein, Douglas M.
, p. 391 - 392 (1999)
Treatment of 4-substituted aryl isocyanates (cf. 2a-f) with NaBH4/TFA leads to the corresponding 4-substituted N,N-bis(2,2,2-trifluoroethyl)aniline derivatives (3a-d) in excellent yield except where an electron-withdrawing group is present (cf.
Carbon-Carbon Bond Formation of Trifluoroacetyl Amides with Grignard Reagents via C(O)-CF3 Bond Cleavage
Zhu, Longzhi,Le, Liyuan,Yan, Mingpan,Au, Chak-Tong,Qiu, Renhua,Kambe, Nobuaki
, p. 5635 - 5644 (2019/05/10)
The reaction of trifluoroacetyl amides with Grignard reagent for the substitution of CF3 group with various alkyl or aryl groups is described. A variety of aryl, quinolin-8-yl, and (hetero)alkyl functional groups as well as F, Cl, and Br atoms are well tolerated. These moisture-stable and easily available trifluoroacetyl amides can be conveniently obtained and used as new versatile precursors for isocyanates. The control experiments show that the reaction proceeds via an isocyanate intermediate and/or alkoxide/amide dual anionic intermediate.
Regioselective ortho-nitration of N-phenyl carboxamides and primary anilines using bismuth nitrate/acetic anhydride
Lu, Yang,Li, Yaming,Zhang, Rong,Jin, Kun,Duan, Chunying
supporting information, p. 9422 - 9427 (2013/10/08)
An efficient and one-pot synthetic method for the regioselective ortho-nitration of the N-phenyl carboxamides and primary anilines has been developed by using bismuth nitrate and acetic anhydride as the nitrating reagents. Reaction proceeds at room temperature and results in corresponding ortho-nitrated products in moderate to excellent yields. This method provides an operationally simple, regioselective, and efficient access to synthesize o-nitro anilines under the mild conditions.