skip to main content
Language:
Search Limited to: Search Limited to: Resource type Show Results with: Show Results with: Search type Index

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

Advanced synthesis & catalysis, 2016-11, Vol.358 (21), p.3368-3372 [Peer Reviewed Journal]

2016 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim ;ISSN: 1615-4150 ;EISSN: 1615-4169 ;DOI: 10.1002/adsc.201600795

Full text available

Citations Cited by
  • Title:
    By-Product-Catalyzed Redox-Neutral Sulfenylation/Deiodination/Aromatization of Cyclic Alkenyl Iodides with Sulfonyl Hydrazides
  • Author: Yang, Fu-Lai ; Gui, Yang ; Yu, Bang-Kui ; Jin, You-Xiang ; Tian, Shi-Kai
  • Subjects: 5]-hydrogen shifts ; [1,5]-hydrogen shifts ; alkenyl iodides ; by-product catalysis ; Byproducts ; Catalysis ; Catalysts ; Decomposition ; Disulfides ; Heating ; Hydrazides ; Iodides ; sulfonyl hydrazides ; thioethers
  • Is Part Of: Advanced synthesis & catalysis, 2016-11, Vol.358 (21), p.3368-3372
  • Description: 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.
  • Publisher: Blackwell Publishing Ltd
  • Language: English
  • Identifier: ISSN: 1615-4150
    EISSN: 1615-4169
    DOI: 10.1002/adsc.201600795
  • Source: Alma/SFX Local Collection
Back to results list
INSPIRE LIBRARY - TON DUC THANG UNIVERSITY (84-028) 37 755 057 Feedback
19 Nguyen Huu Tho St. Dist.7, HCM thuvien@tdtu.edu.vn

Copyright © 2017 INSPIRE LIBRARY - TON DUC THANG UNIVERSITY

Searching Remote Databases, Please Wait