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A New TBAF Complex, Highly Stable, Facile and Selective Source for Nucleophilic Fluorination: Applications in Batch and Flow Chemistry
Asian Journal of Organic Chemistry ( IF 2.7 ) Pub Date : 2020-05-29 , DOI: 10.1002/ajoc.202000235
Madhukar S. Said 1, 2 , Nilesh S. Khonde 1, 2 , Meghana N. Thorat 2, 3 , Ranjit S. Atapalkar 2, 4 , Amol A. Kulkarni 2, 4 , Jayant Gajbhiye 2, 3 , Syed G. Dastager 2, 4
Affiliation  

Natural polysaccharides supported tetrabutylammonium fluoride (TBAF) complexes are prepared and found to be highly stable and selective fluoride source for well‐renowned nucleophilic (SN2 type) fluorination reactions for the first time. Bacterial cellulose, plant cellulose, pectin, and starch derived TBAF complexes are synthesized, characterized (using SEM, TEM, and NMR techniques) and studied for their stability and reactivity. Heterogeneous bacterial cellulose‐TBAF complex (NBu4(Bac‐cell‐OH)F) 1 was found to be highly stable and non‐hygroscopic among all complexes, which gave high yields of fluorinated products in multi‐gram scale in shorter reaction time. The primarily developed batch protocol was extended to solid‐solid continuous flow reaction using an in‐house built screw reactor, which furnished products in a few seconds of residence time (tR=20–25 sec) and excellent yields.

中文翻译:

一种新型的TBAF络合物,高度稳定,方便且选择性的亲核氟化来源:在批量和流动化学中的应用

制备了天然多糖负载的四丁基氟化铵(TBAF)复合物,并首次发现了高稳定性和选择性的氟化物源,用于知名的亲核(SN2型)氟化反应。合成,表征(使用SEM,TEM和NMR技术)鉴定,表征细菌纤维素,植物纤维素,果胶和淀粉的TBAF复合物,并研究其稳定性和反应性。发现异质细菌纤维素-TBAF复合物(NBu4(Bac-cell-OH)F)1在所有复合物中都是高度稳定且不吸湿的,从而在较短的反应时间内即可产生数克级的氟化产物。最初开发的批处理方案已扩展到使用内部构建的螺旋反应器的固-固连续流反应,
更新日期:2020-07-08
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