紫外光诱导1-甲基-2-苯基吲哚啉的合成与表征——国家自然科学基金项目转化的综合型微量有机化学实验

光化学反应是近年来备受青睐的有机合成策略之一,以吲哚啉杂环为骨架的化合物具有多样生物活性,如抗真菌、灭杀害虫、治疗代谢疾病药物等。基于课题组在自然科学基金项目研究中开创的一种绿色光化学吲哚啉合成方法,将部分研究成果设计转化为一个环保型的微量有机化学实验,即在光照下引发苯乙烯和N-甲基邻碘苯胺发生[3+2]自由基环合反应合成1-甲基-2-苯基吲哚啉。将前沿科研成果引入本科生实验教学,既丰富了实验教学内容,又提高了实验教学层次,同时也有助于学生树立“绿色化学”理念,拓宽知识体系。

Regioselective synthesis of α-bromo-α,β-unsaturated carbonyl compounds via photocatalytic α-bromination reactions

A visible light-mediated approach for the preparation of α-bromo-α,β-unsaturated ketones and aldehydes was developed. In comparison to traditional methods that generally take two steps to afford the above compounds, this protocol was highlighted by its operational simplicity, avoiding using hazardous bromine and mild reaction conditions.

Photochemical Studies on Bicyclo[2.1.1]hexyl Derivatives:Chemical Behavior and Asymmetric Induction

The photochemical behavior of bicyclo[2.1.1]hexyl derivatives was investigated by irradiation with a 450 W medium-pressure mercury lamp in acetonitrile solution.The irradiation of methyl bicyclo[2.1.1]hexane-5-carbonylbenzoate(1a)led to both Norrish type II cyclization and cleavage products with a molar ratio of 1∶2.2,whereas the irradiation of methyl 5-methylbicyclo[2.1.1]hexane-5-carbonylbenzoate(1b)afforded the only Norrish/Yang photocyclization compound as the sole product.Such results were illustrated by several geometric parameters for Norrish/Yang photoreaction asφ_(1),φ_(4) andβobtained from the crystal structures.Furthermore,asymmetric pho-tochemical studies using ionic chiral auxiliary technique were also conducted in the solid state.

Electrochemical synthesis of functionalized gem-difluoroalkenes with diverse alkyl sources via a defluorinative alkylation process

An electrochemical defluorinative alkylation protocol ofα-trifluoromethyl alkenes is described.This reaction enables the preparation of functionalized gem-difluoroalkenes with the use of diverse alkyl sources including organohalides,N-hydroxyphthalimide(NHP)esters and Katritzky salts.This method exhibits lots of synthetic advantages including mild conditions,simple operation,and convenience of amplification,and provides a new route for the synthesis of gem-difluoroalkenes。