Hemin Catalyzed Dealkylative Intercepted [2, 3]‐Sigmatropic Rearrangement Reactions of Sulfonium Ylides with 2, 2, 2‐Trifluorodiazoethane | Zendy

Yan Xiaojing | Zendy; Li Chang | Zendy; Xu Xiaofei | Zendy; Zhao Xiaoyong | Zendy; Pan Yuanjiang | Zendy

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Hemin Catalyzed Dealkylative Intercepted [2, 3]‐Sigmatropic Rearrangement Reactions of Sulfonium Ylides with 2, 2, 2‐Trifluorodiazoethane

Author(s) -

Yan Xiaojing,

Li Chang,

Xu Xiaofei,

Zhao Xiaoyong,

Pan Yuanjiang

Publication year - 2020

Publication title -

advanced synthesis and catalysis

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.541

H-Index - 155

eISSN - 1615-4169

pISSN - 1615-4150

DOI - 10.1002/adsc.201901534

Subject(s) - chemistry , sulfonium , allylic rearrangement , catalysis , sigmatropic reaction , diazo , combinatorial chemistry , reactivity (psychology) , hemin , reagent , medicinal chemistry , organosulfur compounds , organic chemistry , sulfur , salt (chemistry) , heme , enzyme , medicine , alternative medicine , pathology

A dealkylative intercepted [2, 3]‐sigmatropic rearrangement reaction of allylic sulfides with 2, 2, 2‐trifluorodiazoethane (CF 3 CHN 2 ) 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 CF 3 CHN 2 , providing excellent yields (up to 99%) under mild condition without inert gas protection. In addition, CF 3 CHN 2 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.

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