Harenberg, Johannes H.; Weidmann, Niels; Knochel, Paul published the artcile< Preparation of Functionalized Aryl, Heteroaryl, and Benzylic Potassium Organometallics Using Potassium Diisopropylamide in Continuous Flow>, SDS of cas: 2127-03-9, the main research area is metalation continuous flow generation organopotassium aromatic hetaryl nucleophile; electrophile addition coupling organopotassium aromatic heterocyclic compound; alc ketone thioether silane preparation organopotassium nucleophile addition coupling; arenes; flow chemistry; heteroarenes; lateral metalation; potassium.
Heterocyclic and aromatic compounds were metalated by lithium-free potassium diisopropylamide serving as nucleophiles in carbonyl group addition and coupling reactions, providing access to versatile substituted benzothiazoles, benzothiophenes, benzofurans and functionalized aromatic compounds We report the preparation of lithium-salt-free KDA (potassium diisopropylamide; 0.6 M in hexane) complexed with TMEDA (N,N,N’,N’-tetramethylethylenediamine) and its use for the flow-metalation of (hetero)arenes between -78° and 25° with reaction times between 0.2 s and 24 s and a combined flow rate of 10 mL min-1 using a com. flow setup. The resulting potassium organometallics react instantaneously with various electrophiles, such as ketones, aldehydes, alkyl and allylic halides, disulfides, Weinreb amides, and Me3SiCl, affording functionalized (hetero)arenes in high yields. This flow procedure is successfully extended to the lateral metalation of methyl-substituted arenes and heteroaromatics, resulting in the formation of various benzylic potassium organometallics. A metalation scale-up was possible without further optimization.
Angewandte Chemie, International Edition published new progress about Alcohols Role: SPN (Synthetic Preparation), PREP (Preparation). 2127-03-9 belongs to class pyridine-derivatives, and the molecular formula is C10H8N2S2, SDS of cas: 2127-03-9.