66087-60-3Relevant articles and documents
Nickel-Catalyzed Oxidative Transamidation of Tertiary Aromatic Amines with N -Acylsaccharins
Liu, Shengzhang,Yang, Lingyun,Tao, Jiasi,Yu, Weijie,Wang, Tao,Fu, Junkai
, p. 1642 - 1646 (2021/06/21)
The use of tertiary amines as surrogates for secondary amines has prominent advantages in terms of stabilization and ease of handling. A Ni-catalyzed transamidation of N -acylsaccharins with tertiary aromatic amines is reported. By using tert -butyl hydroperoxide as the terminal oxidant, this reaction permits selective cleavage of the C(sp 3)-N bonds of unsymmetrical tertiary aromatic amines depending on the sizes of the alkyl substituents.
Transition-Metal-Free Synthesis of 1,2-Disubstituted Indoles
Chesnokov, Gleb A.,Ageshina, Alexandra A.,Topchiy, Maxim A.,Nechaev, Mikhail S.,Asachenko, Andrey F.
supporting information, p. 4844 - 4854 (2019/08/01)
Herein, we report a new transition-metal-free robust and cost-effective method for synthesis of 1,2-disubstituted indoles from easily available unactivated (i.e. without EWG, PPh3 or SiR3 groups) tertiary amides. Scope of synthetic applicability of the presented protocol was shown on 23 examples of 1,2-disubstituted indoles with different substitution patterns obtained in good to excellent yields. The reported method turned out to be especially effective for synthesis of N-arylated 2-CF3-indoles. Moreover, this approach can be performed in a one-pot two-step manner directly from commercially available secondary amines. Mechanistic studies showed that acyl transfer might be an important step in the course of the reaction. Viability of the presented approach for benzofurans and benzothiophenes synthesis was also discussed.
