Synthesis of ω-Chloroalkyl Aryl Ketones via C–C Bond Cleavage of tert-Cycloalkanols with Tetramethylammonium Hypochlorite
Natsumi Hanazawa, Masami Kuriyama, Kosuke Yamamoto, Osamu Onomura
TL;DR
A new method for making ω-chloroalkyl aryl ketones from tert-cycloalkanols using a simple and efficient oxidation process.
Contribution
A metal-free, mild method for C–C bond cleavage using TMAOCl and AcOH without phase-transfer reagents.
Findings
TMAOCl and AcOH effectively promote C–C bond cleavage in a two-phase system.
Unstrained tert-cycloalkanols are converted into ω-chloroalkyl aryl ketones in good yields.
The method operates under mild and metal-free conditions.
Abstract
An oxidative C–C bond cleavage of tert-cycloalkanols with tetramethylammonium hypochlorite (TMAOCl) has been developed. TMAOCl is easy to prepare from tetramethylammonium hydroxide, and the combination of TMAOCl and AcOH effectively promoted the C–C bond cleavage in a two-phase system without additional phase-transfer reagents. Unstrained tert-cycloalkanols were transformed into ω-chloroalkyl aryl ketones in moderate to excellent yields under metal-free and mild reaction conditions.
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Taxonomy
TopicsSynthesis and Catalytic Reactions · Chemical Synthesis and Reactions · Vanadium and Halogenation Chemistry