150596-75-1Relevant academic research and scientific papers
Cobalt-Catalyzed Electrophilic Amination of Aryl- and Heteroarylzinc Pivalates with N-Hydroxylamine Benzoates
Chen, Yi-Hung,Gra?l, Simon,Knochel, Paul
supporting information, p. 1108 - 1111 (2018/01/01)
Aryl- and heteroarylzinc pivalates can be aminated with O-benzoylhydroxylamines at 25 °C within 2–4 h in the presence of 2.5–5.0 % CoCl2?2 LiCl to furnish the corresponding tertiary arylated or heteroarylated amines in good yields. This electrophilic amination also provides access to diarylamines and aryl(heteroaryl)amines. A new tuberculosis drug candidate (Q203) was prepared in six steps and 56 % overall yield by using this cobalt-catalyzed amination as the key step.
Iron(III)-catalyzed C-H functionalization: Ortho-benzoyloxylation of N,N-dialkylanilines and its application to 1,4-benzoxazepines
Chiranjeevi, Barreddi,Vinayak, Botla,Parsharamulu, Thupakula,PhaniBabu, Vemulapalli S.,Jagadeesh, Bharatam,Sridhar, Balasubramanian,Chandrasekharam, Malapaka
, p. 7839 - 7849 (2015/01/16)
A C-O bond-formation reaction that proceeds through C-H functionalization of N,N-dialkylanilines at the ortho-position is presented. The iron-catalyzed selective ortho-benzoyloxylation follows a polar Friedel-Crafts-like mechanism and is sensitive to the nucleophilicity of the anilines. The benzoyl-oxylation of a variety of N,N-disubstituted anilines and Nphenyl heterocycles is carried out under extremely mild conditions. Furthermore, the methodology has been successfully employed for the generation of 1,4-benzoxazepines and oaminophenols.
Lewis Acid-Promoted 3-Aza-Cope Rearrangement of N-Alkyl-N-allylanilines
Beholz, Lars G.,Stille, John R.
, p. 5095 - 5100 (2007/10/02)
The 3-aza-Cope rearrangement of N-alkyl-N-alkylaniline substrates, which required 250 deg C to proceed thermally, was promoted by Lewis acid reagents at 111-140 deg C.Systematic studies of this reaction were performed to examine a number of reaction variables such as concentration, the stoichiometry of the Lewis acid with the substrate, the optimum temperature for rearrangement, and the type of Lewis acid reagent.Of the many Lewis acids investigated, ZnCl2 (140 deg C) and Et2O*BF3 (111 deg C) were the most generally successful reagents for promoting the aromatic 3-aza-Cope rearrangement.With respect to substrate variation, the presence of a methoxy substituent para to the N-allyl group slowed the reaction slightly, while a meta substituent accelerated the rate of rearrangement and produced moderate site selectivity on the aromatic ring.Lewis acid-promoted rearrangement of an unsymmetrically substituted allyl moiety resulted in sigmatropic rearrangement to give the 1-hexen-3-yl substituent on the aromatic ring.Overall, both ZnCl2 and Et2O*BF3 were shown to efficiently accelerate the regiospecific 3-aza-Cope rearrangement of N-alkyl-N-allylanilines for the purpose of forming a carbon-carbon bond between a secondary alkyl substituent and an aromatic ring.
