33342-24-4Relevant academic research and scientific papers
Direct (Hetero)arylation of Heteroarenes Catalyzed by Unsymmetrical Pd-PEPPSI-NHC Complexes under Mild Conditions
Song, A-Xiang,Zeng, Xiao-Xiao,Ma, Bei-Bei,Xu, Chang,Liu, Feng-Shou
, p. 3524 - 3534 (2020/10/09)
With the aim of developing a facile and efficient method to access structurally intriguing and valuable functionalized (hetero)aryls, two unsymmetrical Pd-PEPPSI-type NHC complexes (PEPPSI, pyridine-enhanced precatalyst preparation, stabilization, and initiation; NHC, N-heterocyclic carbene) were designed and synthesized to catalyze the direct arylation of heteroarenes with (hetero)aryl bromides. The results demonstrated that the utilization of this "unsymmetrical"strategy led to much higher efficiency in comparison to the commonly used C2-symmetric Pd-PEPPSI-type NHC complexes. Furthermore, a broad range of heteroaromatics and (hetero)aryl bromide partners with a wide variety of functional groups were all amenable to the developed protocol even at as low as 0.05 mol % catalyst loading and under aerobic conditions. More importantly, along with our study, we also found that the present protocol could provide expedient access to the gram-scale synthesis of the muscle relaxant drug dantrolene and conjugated mesopolymers.
Carbocatalytic reductive coupling reactions: Via electron transfer from graphene to aryldiazonium salt
Morimoto, Naoki,Morioku, Kumika,Suzuki, Hideyuki,Nakai, Yumi,Nishina, Yuta
supporting information, p. 7226 - 7229 (2017/07/11)
A reductive coupling reaction using two-dimensional nanocarbon, i.e., reduced graphene oxide (rGO), as a carbocatalyst and/or a reaction initiator was developed. The radical species on the rGO played an important role in the coupling reaction.
An expedient route to substituted furans via olefin cross-metathesis
Donohoe, Timothy J.,Bower, John F.
supporting information; experimental part, p. 3373 - 3376 (2010/08/05)
The olefin cross-metathesis (CM) reaction is used extensively in organic chemistry and represents a powerful method for the selective synthesis of differentially substituted alkene products. Surprisingly, efforts to integrate this remarkable process into strategies for aromatic and heteroaromatic construction have not been reported. Such structures represent key elements of the majority of small molecule drug compounds; methods for the controlled preparation of highly substituted derivatives are essential to medicinal chemistry. Here we show that the olefin CM reaction, in combination with an acid cocatalyst or subsequent Heck arylation, provides a concise and flexible entry to 2,5-di- or 2,3,5-tri-substituted furans. These cascade processes portend further opportunities for the regiocontrolled preparation of other highly substituted aromatic and heteroaromatic classes.
