Surendra Reddy G, Suresh Kumar A, Ramachary Dhevalapally B
Catalysis Laboratory, School of Chemistry, University of Hyderabad, Hyderabad-500 046, India.
Org Biomol Chem. 2020 Jun 3. doi: 10.1039/d0ob00848f.
An enolate-mediated organocatalytic [3 + 2]-cycloaddition of enones with less reactive vinyl/alkyl/aryl azides is reported at room temperature for short reaction times. The metal-free amine-mediated catalytic conditions of this [3 + 2]-cycloaddition allowed us to synthesize a collection of C/N-double vinyl-1,2,3-triazoles and C-vinyl-1,2,3-triazoles through functionalized enones as quality azidophiles with various azides. It is an efficient catalytic [3 + 2]-cycloaddition for the synthesis of biologically important fully decorated C/N-double vinyl-1,2,3-triazoles with excellent outcomes with reference to the reaction rate, selectivity, operation simplicity, substrate scope, yields, and synthetic applications as demonstrated in the paper. Herein, we illustrated the importance of enolate reactivity with azides compared to enamines by correlation with previous enamine-mediated click reactions in the reaction mechanism section.
据报道，烯醇盐介导的烯酮与活性较低的乙烯基/烷基/芳基叠氮化物的有机催化[3+2]环加成反应在室温下即可短时间内完成。这种[3+2]环加成反应的无金属胺介导催化条件使我们能够通过功能化烯酮作为优质亲叠氮体与各种叠氮化物反应，合成一系列C/N-双乙烯基-1,2,3-三唑和C-乙烯基-1,2,3-三唑。如本文所示，这是一种高效的催化[3+2]环加成反应，用于合成具有生物学重要性的完全修饰的C/N-双乙烯基-1,2,3-三唑，在反应速率、选择性、操作简便性、底物范围、产率和合成应用方面都有出色的结果。在此，我们在反应机理部分通过与之前的烯胺介导点击反应进行关联，阐述了烯醇盐与叠氮化物反应活性相对于烯胺的重要性。
