Iron-catalyzed reductive cyclization of nitroarenes: Synthesis of aza-heterocycles and DFT calculations  

作　　者：Christine Tran Aicha Abdallah Valentin Duchemann Guillaume Lefevre Abdallah Hamze 

机构地区：[1]CNRS,BioCIS,UniversitéParis-Saclay,Chatenay-Malabry 92290,France [2]Chimie ParisTech,CNRS,Institute of Chemistry for Life and Health Sciences,PSL University,CSB2D,Paris 75005,France

出　　处：《Chinese Chemical Letters》2023年第3期337-341,共5页中国化学快报（英文版）

摘　　要：Research into environmentally friendly strategies for hydrogen transfer reduction is increasing, along with the need for more elaborate heterocyclic platforms. Within this context, we develop a new approach for substituted dihydrobenzo[c]carbazoles and indoles. These compounds were synthesized through an iron-catalyzed hydrogen transfer reduction of nitroarenes, followed by intramolecular cyclization. This transformation involves using a Kn?lker-type catalyst, Cs_(2)CO_(3) as the base, and benzyl alcohol as the nonexpensive and low volatile hydrogen donor. We synthesize 30 examples of aza-heterocycles with moderate to excellent yields by applying this strategy. Additionally, DFT calculations demonstrated that the pathway reaction could follow an anionic mechanism.

关 键 词：Iron CYCLIZATION NITROARENES Dihydrobenzo[c]carbazoles INDOLES 

分 类 号：O626[理学—有机化学] O641.1[理学—化学]