37846-06-3Relevant articles and documents
Iodine-Promoted Metal-Free Cyclization and O/S Exchange of Acrylamides with Thiuram: One-Step Synthesis of Quinolino-2-thiones
Jiao, Jing,Xiao, Fangtao,Wang, Cheng,Zhang, Zhipeng
supporting information, p. 4965 - 4970 (2022/04/07)
A one-step cyclization and O/S exchange reaction of readily available acrylamides in the presence of iodine and thiuram has been developed. The reaction provides an efficient approach for the synthesis of highly important heterocycle quinolino-2-thiones with diverse substitution patterns.
A Metal-Free Direct Arene C?H Amination
Wang, Tao,Hoffmann, Marvin,Dreuw, Andreas,Hasagi?, Edina,Hu, Chao,Stein, Philipp M.,Witzel, Sina,Shi, Hongwei,Yang, Yangyang,Rudolph, Matthias,Stuck, Fabian,Rominger, Frank,Kerscher, Marion,Comba, Peter,Hashmi, A. Stephen K.
supporting information, p. 2783 - 2795 (2021/04/05)
The synthesis of aryl amines via the formation of a C?N bond is an essential tool for the preparation of functional materials, active pharmaceutical ingredients and bioactive products. Usually, this chemical connection is only possible by transition metal-catalyzed reactions, photochemistry or electrochemistry. Here, we report a metal-free arene C?H amination using hydroxylamine derivatives under benign conditions. A charge transfer interaction between the aminating reagents TsONHR and the arene substrates enables the chemoselective amination of the arene, even in the presence of various functional groups. Oxygen was crucial for an effective conversion and its accelerating role for the electron transfer step was proven experimentally. In addition, this was rationalized by a theoretical study which indicated the involvement of a dioxygen-bridged complex with a “Sandwich-like” arrangement of the aromatic starting materials and the aminating agents at the dioxygen molecule. (Figure presented.).
Room temperature N-heterocyclic carbene manganese catalyzed selective N-alkylation of anilines with alcohols
Huang, Ming,Li, Yukui,Li, Yinwu,Liu, Jiahao,Shu, Siwei,Liu, Yan,Ke, Zhuofeng
supporting information, p. 6213 - 6216 (2019/06/07)
The first example of room temperature non-noble metal homogeneous system catalyzed selective N-alkylation of anilines with alcohols by a bis-NHC manganese complex is presented. This system was applied to a large range of alcohols and anilines, including biologically relevant motifs and challenging methanol. Experimental and computational studies suggest an outer-sphere mechanism for this NHC-Mn system.