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A New TBAF Complex, Highly Stable, Facile and Selective Source for Nucleophilic Fluorination: Applications in Batch and Flow Chemistry
Author(s) -
Said Madhukar S.,
Khonde Nilesh S.,
Thorat Megha.,
Atapalkar Ranjit S.,
Kulkarni Amol A.,
Gajbhiye Jayant,
Dastager Syed G.
Publication year - 2020
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.202000235
Subject(s) - chemistry , nucleophile , cellulose , sn2 reaction , flow chemistry , fluoride , organic chemistry , combinatorial chemistry , catalysis , inorganic chemistry
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.