Efficient Procedures to Prepare Primary and Secondary Alkyl Halides from Alkanols via the Corresponding Sulfonates under Mild Conditions
Efficient Procedures to Prepare Primary and Secondary Alkyl Halides from Alkanols via the Corresponding Sulfonates under Mild Conditions
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DOI：
10.1002/adsc.201100736
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发表时间：
2012-05-01
影响因子：
5.4
通讯作者：
Delacroix, Thomas
中科院分区：
文献类型：
--
作者：
Cahiez, Gerard;Gager, Olivier;Delacroix, Thomas
本文提出的研究表明，磺酸盐/卤化物交换可以有利地在THF中进行，以避免几个副反应，如消除和差向异构化，当反应从手性烷基磺酸盐或具有C？H酸性手性中心。发现该方法的主要限制是仲烷基磺酸盐转化为烷基氯。在这种情况下，加入催化量的氯化锰明显加速了反应的速率和效率。
The study presented herein shows that sulfonate/halide exchange can be advantageously performed in THF to avoid several side reactions such as elimination and epimerization when the reaction is performed from a chiral alkyl sulfonate or a substrate having a C?H acidic chiral center. The main limitation of this procedure was found to be the conversion of secondary alkyl sulfonates to alkyl chlorides. In this case, the addition of a catalytic amount of manganese chloride clearly accelerates the rate and the efficiency of the reaction.