A mild and convenient method for the allylic chlorination of naturally occurring terpenic olefins was investigated in the presence of different supported and non-supported Lewis acid catalysts. The reaction has been tested on carvone as a model substrate in the presence of sodium hypochlorite as chlorine donor. The scope and limitations of transition metal-based Lewis acid catalysts, stoichiometry, and substrate structure were evaluated. Among the iron precursors used, FeCl3 and FeCl2 provide the promise of a general approach to allylic or vinylic chlorination reaction. Various terpenic olefins were examined in the presence of FeCl3/NaOCl combination system. The catalytic chlorination proceeds under mild conditions with short reaction time and shows a high selectivity affording the corresponding chlorides in good to excellent yields.

中文翻译：

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使用负载型和非负载型路易斯酸催化剂对天然萜烯进行烯丙基氯化

在不同负载型和非负载型路易斯酸催化剂存在下，研究了一种温和方便的天然萜烯烯丙基氯化方法。在作为氯供体的次氯酸钠存在下，在作为模型底物的香芹酮上测试了该反应。评估了基于过渡金属的路易斯酸催化剂、化学计量和底物结构的范围和局限性。在所使用的铁前体中，FeCl3 和 FeCl2 有望成为烯丙基或乙烯基氯化反应的通用方法。在 FeCl3/NaOCl 组合体系存在下检测了各种萜烯。催化氯化在温和条件下进行，反应时间短，显示出高选择性，以良好到极好的收率提供相应的氯化物。