Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 358, Issue 21, Pages 3368-3372Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201600795
Keywords
alkenyl iodides; by-product catalysis; [1,5]-hydrogen shifts; sulfonyl hydrazides; thioethers
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Funding
- National Natural Science Foundation of China [21472178, 21232007, 21502182]
- National Key Basic Research Program of China [2014CB931800]
- Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20000000]
- FRFCU [WK2060190048]
- China Postdoctoral Science Fundation [2015M571937]
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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.
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