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Article Abstract
We report a novel halogen-bond-assisted NHC-catalyzed (dynamic) kinetic resolution strategy for the synthesis of axially chiral heterobiaryls. A class of axially chiral quinolines are prepared efficiently in excellent enantioselectivities (≤98% ee) employing 3-5 mol % NHC catalyst. Mechanistic studies reveal the indispensability of 5-bromo-2-iodobenzaldehyde in this reaction, in which a pivotal halogen bonding interaction plays a crucial role in the process.
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Similar Publications
Halogen-Bond-Assisted NHC-Catalyzed (Dynamic) Kinetic Resolution for the Atroposelective Synthesis of Heterobiaryls.
Org Lett
October 2024
Key Laboratory of Synthetic and Natural Functional Molecule of the Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi'an 710127, P. R. China.
Article Synopsis
- A new method using halogen bonds and NHC catalysts allows for the efficient synthesis of axially chiral heterobiaryls, specifically quinolines.
- The process achieves excellent enantioselectivities of up to 98% with a low catalyst load of 3-5 mol %.
- Mechanistic investigations highlight the necessity of 5-bromo-2-iodobenzaldehyde, which is critical for the halogen bonding interaction that drives the reaction.