By-Product-Catalyzed Redox-Neutral Sulfenylation/Deiodination/Aromatization of Cyclic Alkenyl Iodides with Sulfonyl Hydrazides
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. (Figure presented.).
Iodine-Promoted Tunable Synthesis of 2-Naphthyl Thioethers and 1-Naphthyl Thioethers
An iodine-promoted regioselective sulfenylation/deoxygenation/aromatization reaction of 1-tetralones with disulfides has been developed. This process could be modified to synthesize 2-naphthyl thioethers and 1-naphthyl thioethers in moderate to excellent
Diazaphospholane as an efficient ligand for copper-catalyzed cross-coupling of thiols with aryl iodides
Copper-catalyzed cross-coupling of thiols with aryl iodides performed well using an air-stable diazaphospholane ligand in presence of NaOH in DMF at 110 °C and a variety of diaryl sulfides are synthesized in good yields.
Yang, Minghua,Pei, Ji,Yan, Guobing,Zheng, Yunfa
experimental part
p. 587 - 591
(2012/05/31)
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