Facile Synthesis of α‐Haloketones by Aerobic Oxidation of Olefins Using KX as Nonhazardous Halogen Source,Chinese Journal of Chemistry

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Facile Synthesis of α‐Haloketones by Aerobic Oxidation of Olefins Using KX as Nonhazardous Halogen Source
Chinese Journal of Chemistry ( IF 5.5 ) Pub Date : 2019-12-24 , DOI: 10.1002/cjoc.201900372
Zhibin Luo ₁ , Yunge Meng ₁ , Xinchi Gong ₁ , Jie Wu ₁ , Yulan Zhang ₁ , Long‐Wu Ye ₂ , Chunyin Zhu _{1,

2}

Affiliation

An operationally simple and safe synthesis of α‐haloketones using KBr and KCl as nonhazardous halogen sources is reported. It involves an iron‐catalysed reaction of alkenes with KBr/KCl using O₂ as terminal oxidant under the irradiation of visible‐light. This strategy avoids the risks associated with handling halo‐contained electrophiles (Cl₂, Br₂, NCS, NBS). The process is tolerant to several functional groups, and extended to a range of substituted styrenes in up to 89% yield. A radical reaction pathway is proposed based on control experiments and spectroscopy studies.

中文翻译：

以KX为无害卤素源的烯烃好氧氧化法轻松合成α-卤代酮

据报道，使用KBr和KCl作为无害卤素源，可以简单，安全地合成α-卤代酮。它涉及在可见光照射下，以O ₂为末端氧化剂，烯烃与KBr / KCl的铁催化反应。该策略避免了与处理含卤亲电试剂（Cl ₂，Br ₂，NCS，NBS）相关的风险。该方法可耐受多个官能团，并以高达89％的收率扩展到一系列取代苯乙烯。基于控制实验和光谱学研究，提出了自由基反应途径。

更新日期：2019-12-25

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