Base-Catalyzed Deprotection of Aldehydes: A New Haloform Reaction
Gulizhabaier Abulipizi, Kadierya Abuduwaili, Shiying Tian, Mailikezhati Maihemuti*, Abudu Rexit Abulikemu*
*Xinjiang University, Urumqi 830046; Xinjiang Normal
University, Urumqi 830054, P. R. of China,
Email: amelikezat
xju.edu.cn, aarexitxjnu.edu.cn
G. Abulipizi, K. Abuduwaili, S. Tian, M. Maihemuti, A. R. Abulikemu, Synthesis, 2024, 56, 482-486.
DOI: 10.1055/a-2201-3503
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Abstract
An efficient procedure for the deprotection of α,α,α-trihalogen (Cl, Br) methyl alcohols provides the corresponding aldehydes and haloforms under mild reaction conditions. This method can be applied to the deprotection of aromatic, aliphatic, and heterocyclic trihalomethyl alcohol compounds.
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Details
The document describes a new method for the base-catalyzed deprotection of α,α,α-trihalogen (Cl, Br) methyl alcohols to produce corresponding aldehydes and haloforms under mild conditions. This method is applicable to aromatic, aliphatic, and heterocyclic trihalomethyl alcohol compounds. The study found that potassium tert-butoxide (t-BuOK) in anhydrous tetrahydrofuran (THF) at room temperature is the most effective base and solvent combination, yielding high efficiency and high yields of deprotected aldehydes. The reaction mechanism involves the formation of an unstable oxygen anion intermediate under alkaline conditions, leading to the generation of aldehydes and haloforms. The method was successfully applied to various substrates, including those with electron-withdrawing and electron-donating groups, and was scalable to gram quantities. The research highlights the practicality and efficiency of this deprotection method, offering a novel approach to haloform reactions. The study was supported by the Natural Science Foundation of Xinjiang Uygur Autonomous Region of China and declares no conflict of interest. Detailed experimental procedures and NMR data for the synthesized compounds are provided, ensuring reproducibility and verification of the results.
Key Words
trihalohydrins, aldehydes, deprotection, haloform reaction
ID: J66-Y2024
