Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 30, Pages 12321-12325Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202003392
Keywords
arenes; flow chemistry; heteroarenes; lateral metalation; potassium
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Funding
- German Academic Scholarship Foundation
- DFG
- LMU
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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 degrees C and 25 degrees C with reaction times between 0.2 s and 24 s and a combined flow rate of 10 mL min(-1) using a commercial 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.
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