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褚雪强、沈志良团队在J. Org. Chem.发表论文
阅读次数: 添加时间:2021/08/19 发布:

Three-Component Bisannulation for the Synthesis of Trifluoromethylated Tetracyclic Aza-Aromatics through Six C(sp3)−F Bond Cleavage and Four C−N Bond Formation

Qing-Dong Wang,*a,b Ya-Wen Wang,a Ting Xie,a Yan-Ying Cui,a Mengtao Ma,c Zhi-Liang Shen,a and Xue-Qiang Chu*a

a Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, China.

b School of Pharmacy, Yancheng Teachers University, Yancheng 224007, China.

c Department of Chemistry and Materials Science, College of Science, Nanjing Forestry University, Nanjing 210037, China.

 

Abstract: An unprecedented and expeditious tandem bisannulation of polyfluoroalkylated tetralones with benzamidines to access various fluoroalkyl tetracyclic [1,3]-diazepines through multiple C-N bond formation and C(sp3)-F bond cleavage is reported. The process features high regio/chemoselectivities, broad substrate scope, good functional group tolerance, procedural simplicity, mild reaction conditions, and scale-up synthesis. Mechanistic studies showed that the distinctive fluorine-effect of polyfluoroalkyl tetralone plays a vital role for the aza-tetracycle construction.

 

J. Org. Chem. 2021, 86, 8236-8247. (Impact factor: 4.35)

论文链接:https://pubs.acs.org/doi/10.1021/acs.joc.1c00695.

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