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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.