Department of Chemistry, School of Natural Sciences, Shiv Nadar Institution of Eminence Deemed to be University, Chithera, Dadri, Gautam Buddha Nagar, UP 201314, India.
Department of Chemistry, SRM-AP, Amaravati, AP, India.
Org Biomol Chem. 2023 Jul 12;21(27):5592-5600. doi: 10.1039/d3ob00791j.
An expedient and operationally convenient mechanochemical synthesis of aryl/heteroaryl -sulfonyl imines is reported by reacting iminoiodinanes with numerous aryl/heteroaryl benzyl alcohols in ball milling apparatus (RETSCH 400™) with three 5 mm stainless steel (ss) balls in a 5 mL stainless steel (ss) reaction jar. CHCl ( = 0.2-0.4 μL mg) was used as a liquid assisted grinding (LAG) auxiliary. This metal catalyst- and base- free synthesis with nominal amounts of solvents (as LAGs) demonstrated an efficient -sulfonyl transfer reaction from iminoiodinanes to afford the desired compounds in moderate to good yields. Substituted -sulfonyl imines are crucial as standalone natural product building blocks and drug intermediates as well as precursors of sulfonamides which have been involved in potential small molecule therapy in many therapeutic programs. The putative mechanisms of the transformations are discussed based on control reactions and DFT calculations.
本文报道了一种简便、可操作的机械化学合成方法，通过在球磨机（RETSCH 400™）中用 3 个 5mm 不锈钢球在 5ml 不锈钢反应罐中，将亚胺碘烷与多种芳基/杂芳基苄醇反应，以 CHCl（=0.2-0.4μL mg）作为液体辅助研磨（LAG）助剂。该方法无需金属催化剂和碱，只需使用少量溶剂（作为 LAG），即可有效地从亚胺碘烷中进行 - 磺酰基转移反应，以中等至良好的收率得到所需的化合物。取代的磺酰亚胺作为独立的天然产物构建块和药物中间体，以及磺酰胺的前体，在许多治疗方案中都涉及到潜在的小分子治疗。基于对照反应和 DFT 计算，讨论了这些转化的可能机制。
