- Hemin Catalyzed Dealkylative Intercepted [2, 3]-Sigmatropic Rearrangement Reactions of Sulfonium Ylides with 2, 2, 2-Trifluorodiazoethane
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A dealkylative intercepted [2, 3]-sigmatropic rearrangement reaction of allylic sulfides with 2, 2, 2-trifluorodiazoethane (CF3CHN2) is reported, the commercially available and biocompatible catalyst hemin was found to efficiently catalyze this transformation across a diverse set of allylic sulfides with in situ generated CF3CHN2, providing excellent yields (up to 99%) under mild condition without inert gas protection. In addition, CF3CHN2 exhibited unique reactivity toward this process compared with other frequently used diazo reagents. This work expands the range of carbene-mediated transformations catalyzed by hemin and introduces a concise and general strategy for exploiting new possibility of reactions concerning organosulfides. (Figure presented.).
- Yan, Xiaojing,Li, Chang,Xu, Xiaofei,Zhao, Xiaoyong,Pan, Yuanjiang
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supporting information
p. 2005 - 2011
(2020/05/18)
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- Rh(II)-Catalyzed [2,3]-Sigmatropic Rearrangement of Sulfur Ylides Derived from Cyclopropenes and Sulfides
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(Chemical Equation Presented) A new type of Rh2(OAc)4-catalyzed [2,3]-sigmatropic rearrangement of sulfur ylides is reported. A series of cyclopropenes were successfully employed for [2,3]-sigmatropic rearrangement by a reaction with either allylic or propargylic sulfides. Under the optimized conditions, the reaction afforded the products in moderate to excellent yields. In these transformations, the vinyl metal carbenes generated in situ from the cyclopropenes were effectively trapped by sulfides, resulting in the formation of corresponding products upon [2,3]-sigmatropic rearrangements.
- Zhang, Hang,Wang, Bo,Yi, Heng,Zhang, Yan,Wang, Jianbo
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supporting information
p. 3322 - 3325
(2015/07/15)
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- Nickel-catalyzed electrochemical synthesis of dihydro-berazo[b]thiophene derivatives
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The intramolecular electrochemical reductive cyclization of orthohaloaryl allyl thioethers catalyzed by Ni(II) complexes associated to cyclam ligands affords dihydro-benzo[b]thiophene derivatives in moderate to good yields.
- Pelletier, Jeremie,Olivero, Sandra,Dunach, Elisabet
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p. 3343 - 3348
(2007/10/03)
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- Ytterbium metal promoted allylation of disulfides with allyl bromide
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In the presence of a catalytic amount of methyliodide, ytterbium metal can promote the reductive cleavage of the S-S bond in disufides 1 to give ytterbium thiolates 2 which then react with allyl bromide to form the corresponding allylic sulfides 3 in good yields under mild and neutral conditions.
- Su, Weike,Li, Yongshu,Zhang, Yongmin
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p. 2101 - 2106
(2007/10/03)
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