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Abstract
Herein, we describe the generation of highly reactive monoalkyl and phenyl ketenes by using a dehalogenation procedure under flow conditions. All ketenes were generated in good yields (determined by quenching with an appropriate aniline derivative) and showed high reactivity in the [2+2] cycloaddition with imines, resulting in the formation of a range of β-lactams at room temperature in less than 10 minutes. Furthermore, initial experiments were performed by using these reactive ketenes for the synthesis of β-lactams under flow conditions.
Highlights
Syn lettGeneration of Reactive Ketenes under Flow Conditions through Zinc-Mediated Dehalogenation
The generation and control of reactive/unstable intermediates is a fundamental part of organic chemistry because it allows the synthesis of unique molecular structures
The method of choice for reactions with these reactive ketenes is their generation in situ, starting from the corresponding acyl chloride in the presence of a tertiary amine base and an appropriate coupling partner.[4]
Summary
Generation of Reactive Ketenes under Flow Conditions through Zinc-Mediated Dehalogenation. Dedicated to Peter Vollhardt, dear friend and academic founder of Synlett.
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