80485-15-0Relevant academic research and scientific papers
Hemin Catalyzed Dealkylative Intercepted [2, 3]-Sigmatropic Rearrangement Reactions of Sulfonium Ylides with 2, 2, 2-Trifluorodiazoethane
Yan, Xiaojing,Li, Chang,Xu, Xiaofei,Zhao, Xiaoyong,Pan, Yuanjiang
, p. 2005 - 2011 (2020/05/18)
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.).
Enabling iron catalyzed Doyle-Kirmse rearrangement reactions with: In situ generated diazo compounds
Hock, Katharina J.,Mertens, Lucas,Hommelsheim, Renè,Spitzner, Robin,Koenigs, Rene M.
supporting information, p. 6577 - 6580 (2017/07/10)
Slow addition of sodium nitrite allows the in situ preparation of highly explosive diazo compounds and enables their safe and scalable application in iron catalyzed rearrangement reactions of allylic and propargylic sulfides. With catalyst loadings as low as 0.1 mol% an effective entry into α-mercapto-nitriles, α-mercapto-esters and α-trifluoromethyl-sulfides on a gram-scale is achieved.
Aryne triggered [2,3]-sigmatropic rearrangement of allyl and propargyl thioethers
Tan, Jiajing,Zheng, Tianyu,Xu, Kun,Liu, Changyao
supporting information, p. 4946 - 4950 (2017/07/10)
An efficient protocol for [2,3]-sigmatropic rearrangement of allyl and propargyl thioethers is reported. The key sulfonium ylide intermediate is in situ formed via S-arylation of arynes. This transition metal-free method allows for ready access to a wide
SYNTHESIS OF DIENES WITH 1,1-CAPTODATIVE SUBSTITUTION
Mesmaeker, N. Stevenart-De,Merenyi, R.,Viehe, H. G.
, p. 2591 - 2594 (2007/10/02)
1,1-Captodative butadienes carrying amino, thioether or methoxy groups combined with nitrile and ester substituents were synthesized via a sigmatropic rearrangement, an alkylation-halogenation-dehydrohalogenation sequence or via the Wittig-Horner re
