49678-88-8Relevant academic research and scientific papers
Development of electrochemical processes for nitrene generation and transfer
Siu, Tung,Picard, Christine J.,Yudin, Andrei K.
, p. 932 - 937 (2005)
(Chemical Equation Presented) An electrochemical strategy for running nitrogen-transfer reactions on chemically inert anode surfaces has been developed. The generation and trapping of highly reactive nitrene-transfer reagents can be accomplished under mild conditions on platinum electrodes. The key factor that accounts for the high levels of chemoselectivity in this process is the phenomenon of overpotential. We have found that molecules that are similar in terms of propensity toward oxidation can be differentiated on the basis of their affinity to a given electrode surface. Thereby, reactive species can be selectively generated in the presence of acceptor molecules of interest. Specifically, a wide range of structurally dissimilar olefins can be transformed into the corresponding aziridines in the presence of N-aminophthalimide. Likewise, nitrene generation in the presence of sulfoxides leads to their chemoselective transformation into the corresponding sulfoximines. In this paper we discuss the underlying mechanistic foundation of these reactions.
Metal-free synthesis of 1,2-amino alcohols by one-pot olefin aziridination and acid ring-opening
Hua, Yong-Gang,Yang, Qian-Qian,Yang, Yi,Wang, Mei-Jing,Chu, Wen-Chao,Bai, Peng-Yan,Cui, De-Yun,Zhang, En,Liu, Hong-Min
supporting information, p. 2748 - 2751 (2018/06/12)
A one-pot, two-step reaction comprising olefin aziridination and ring-opening of an aziridine intermediate to synthesize 1,2-amino alcohols has been developed. This reaction is suitable for several types of olefin. This methodology allows an efficient and
Sodium-iodoxybenzoate mediated highly chemoselective aziridination of olefins
Bakthavachalam, Ananthan,Chuang, Hui-Chun,Yan, Tu-Hsin
, p. 5884 - 5894 (2015/03/30)
Herein we utilized, for the first time, sodium 2-iodoxybenzoate as a highly specific oxidant for PhthNH2 to create a highly chemoselective aziridination reagent. This method efficiently effects aziridination of electron-rich, electron-deficient, allylic alcohol and alkenyl bromide C=C bonds in good to excellent yields. Inter and intramolecular chemoselectivity was demonstrated between electron-rich and electron-deficient alkenes by using this efficient and metal free protocol.
Aryl iodide mediated aziridination of alkenes
Li, Jiayin,Chan, Philip Wai Hong,Che, Chi-Ming
, p. 5801 - 5804 (2007/10/03)
(Chemical Equation Presented) Aryl iodide mediated aziridination of a variety of alkenes with N-aminophthalimide under mild conditions (m-CPBA, K 2CO3, CH2Cl2, 25°C) was achieved in moderate to good yields (up to 94%). By recovering the aryl iodide, a recyclable system is developed with product yield over 79% attained for the aziridination of trans-1,2-diphenylethylene.
Practical olefin aziridination with a broad substrate scope
Siu, Tung,Yudin, Andrei K.
, p. 530 - 531 (2007/10/03)
The present study illustrates the possibility of a rational approach that bypasses the requirement for stoichiometric amounts of toxic oxidants and metal additives (including reagents and catalysts) in organic redox reactions. We describe an aziridination process that delivers a nitrene functionality to olefins from a readily available N-aminophthalimide. Remarkably, both electron-rich and electron-poor olefins are converted to aziridines with high efficiency. The continuum of applied potentials and the heterogeneous nature of reactions at electrode surfaces allow for the electrochemical discrimination of substrates which have similar redox potentials and therefore cannot be selectively reduced or oxidized using soluble reagents. This selectivity is due to the phenomenon of overpotential, the kinetic inhibition of electron transfer on a particular electrode surface. Copyright
