Faculty of Chemistry, Bu-Ali-Sina University, 65174-38683, Hamedan, Iran.
Sci Rep. 2020 Oct 21;10(1):17904. doi: 10.1038/s41598-020-74733-2.
This study is the first report of electrochemical generation of hydroxyimino-cyclohexa-dien-ylidene haloniums and their application in the synthesis of new halo-N-hydroxysulfonamide derivatives. These compounds were obtained in a one-pot process based on the reaction of halonium acceptors with arylsulfinic acids. The method is easy to carry out, as it is performed using the carbon electrodes in a simple undivided cell. The protocol has a broad substrate scope with a tolerance for a variety of functional groups. The proposed mechanism is a ping-pong type reaction mechanism, which in its first stage the halonitroarene is reduced at the cathode to related hydroxylamine and in the second stage the cathodically generated hydroxylamine by oxidation at the anode and participating in disproportionation reaction is converted to the halonium acceptor.
这项研究首次报道了羟亚氨基环己二烯基卤𬭩盐的电化学生成及其在新型卤代-N-羟基磺酰胺衍生物合成中的应用。这些化合物是通过卤𬭩受体与芳基亚砜酸反应一锅法得到的。该方法易于实施，因为它是在简单的不分流电池中使用碳电极进行的。该方案具有广泛的底物范围，对各种官能团具有耐受性。所提出的机制是乒乓反应机制，在第一阶段，卤硝芳烃在阴极还原为相关的羟胺，在第二阶段，阴极生成的羟胺在阳极氧化并参与歧化反应转化为卤𬭩受体。
