By-Product-Catalyzed Redox-Neutral Sulfenylation/Deiodination/Aromatization of Cyclic Alkenyl Iodides with Sulfonyl Hydrazides

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• 作者：Fu-Lai Yang ; Yang Gui ; Bang-Kui Yu ; You-Xiang Jin and Shi-Kai Tian
• 刊名：Advanced Synthesis & Catalysis
• 出版年：2016
• 出版时间：November 3, 2016
• 年：2016
• 卷：358
• 期：21
• 页码：3368-3372
• 全文大小：376K
• ISSN：1615-4169

文摘

A by-product-catalyzed redox-neutral process has been established through tandem sulfenylation/deiodination/aromatization of cyclic alkenyl iodides with sulfonyl hydrazides. In the absence of external catalysts and additives a range of 4-iodo-1,2-dihydronaphthalenes reacted with sulfonyl hydrazides to give structurally diverse 2-naphthyl thioethers in good yields. Mechanistic studies showed that at an early stage sulfonyl hydrazides decomposed completely to thiosulfonates and disulfides and at a late stage the resulting thiosulfonates underwent tandem sulfenylation/deiodination/aromatization with 4-iodo-1,2-dihydronaphthalenes involving a [1,5]-sigmatropic hydrogen shift. Importantly, iodine was generated as a by-product from 4-iodo-1,2-dihydronaphthalenes upon heating and served as a catalyst for the decomposition of sulfonyl hydrazides and subsequent formation of 2-naphthyl thioethers.