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- Title
"Snapshot" Trapping of Multiple Transient Azolyllithiums in Batch.
- Authors
Inoue, Kengo; Feng, Yuxuan; Mori, Atsunori; Okano, Kentaro
- Abstract
Recent developments in flow microreactor technology have allowed the use of transient organolithium compounds that cannot be realized in a batch reactor. However, trapping the transient aryllithiums in a "halogen dance" is still challenging. Herein is reported the trapping of such short‐lived azolyllithiums in a batch reactor by developing a finely tuned in situ zincation using zinc halide diamine complexes. The reaction rate is controlled by the appropriate choice of diamine ligand. The reaction is operationally simple and can be performed at 0 °C with high reproducibility on a multigram scale. This method was applicable to a wide range of brominated azoles allowing deprotonative functionalization, which was used for the concise divergent syntheses of both constitutional isomers of biologically active azoles.
- Subjects
ZINC halides; BATCH reactors; ISOMERS; ORGANOLITHIUM compounds; AZOLES; HALOGENS; CARBANIONS
- Publication
Chemistry - A European Journal, 2021, Vol 27, Issue 40, p10267
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.202101256