Enantiospecific on-water bromination: a mild and efficient protocol for the preparation of alkyl bromides,Green Chemistry

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Enantiospecific on-water bromination: a mild and efficient protocol for the preparation of alkyl bromides
Green Chemistry ( IF 9.3 ) Pub Date : 2020-11-12 , DOI: 10.1039/d0gc02855j
Francesco Alletto _{1,

2,

3,

4,

5} , Mauro F. A. Adamo _{1,

2,

3,

4,

5}

Affiliation

Herein we report the first example of an on-water enantiospecific synthesis of alkyl bromides. This procedure allowed the conversion of secondary activated alkyl sulphides to benzylic alkyl bromides, which were obtained in 80–99% yields. The reaction carried out on enantio-pure sulphides provided the corresponding bromides in high yields and enantioselectivity (up to 92% ee; 94% es) at room temperature. The on-water conditions reduced significantly the reaction times compared to similar procedures run in organic media. The condition identified made use of no solvent, required no temperature control and produced a smooth organic phase easily separated for further synthetic use on a multigram-scale without the need for any organic extraction. Therefore, the present constitutes the most operationally simple and environmentally benign approach to a class of much sought organic intermediates.

中文翻译：

对映体特异性水上溴化：温和而有效的方案，用于制备烷基溴化物

在本文中，我们报告了烷基溴的水对映体特异性合成的第一个例子。该程序允许将次级活化烷基硫化物转化为苄基烷基溴化物，其收率为80-99％。在室温下，对映体纯的硫化物进行的反应以高收率和对映体选择性（最高92％ee; 94％es）提供了相应的溴化物。与在有机介质中运行的类似程序相比，水上条件显着减少了反应时间。所确定的条件不使用溶剂，不需要控制温度，并且产生了易于分离的光滑有机相，可用于数克规模的进一步合成用途，而无需任何有机萃取。因此，

更新日期：2020-11-25

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