Electrochemical synthesis of γ-keto sulfones containing a β-quaternary carbon center <i>via</i> 1,2-migration
作者:Wen Xia、Yawen Yang、Xiaohui Zhang、Liangzhen Hu、Yan Xiong
DOI:10.1039/d3gc02128a
日期:——
An effective electrochemical rearrangement reaction, both oxidant and metal catalyst-free, is presented to construct γ-keto sulfones containing a β-quaternary carbon center in this study. In the protocol, radicals are generated from benzenesulfonyl hydrazines, which cause 1,2-migrations of starting materials, 2-methylallyl alcohol derivatives, and formation of new C–C and C–S bonds. A series of aryl-migration
本研究提出了一种有效的电化学重排反应,无需氧化剂和金属催化剂,可以构建含有β-季碳中心的γ-酮基砜。在该方案中,苯磺酰肼产生自由基,引起起始材料、2-甲基烯丙醇衍生物的1,2-迁移,并形成新的C-C和C-S键。以良好的收率获得了一系列芳基迁移、烷基迁移和扩环产物,并具有优异的官能团耐受性。克级反应表明电氧化重排策略具有工业实用性的潜力。此外,根据现有文献报告、对照实验和循环伏安图,提出了一种可能且合理的机制。