50707-39-6Relevant articles and documents
Catalytic Asymmetric [3 + 2] Annulation of Hantzsch Esters with Racemic N-Sulfonylaziridines
Chai, Zhuo,Ma, Chen-Xue,Yang, Gaosheng,Yang, Pei-Jun,Zhu, Guo-Sheng
supporting information, p. 7933 - 7937 (2021/10/25)
Hantzsch esters (HEs) served as two-carbon partners in a copper(I)-catalyzed enantioselective [3 + 2] annulation with racemic 2-(hetero)aryl-N-sulfonyl aziridines via kinetic resolution to provide pyrrolo[2,3-b]tetrahydropyridines containing multiple contiguous stereogenic centers including all-carbon quaternary centers in excellent yields and enantiopurities and moderate-to-excellent diastereoselectivities. Mainly dependent upon the structures of the aziridines, a competitive hydrogenolysis process with HEs as the hydrogen source was also observed in some cases.
Copper iodide-catalyzed aziridination of alkenes with sulfonamides and sulfamate esters
Chang, Joyce Wei Wei,Ton, Thi My Uyen,Zhang, Zhengyang,Xu, Yanjun,Chan, Philip Wai Hong
scheme or table, p. 161 - 164 (2009/04/14)
An efficient copper iodide-catalyzed aziridination of a variety of alkenes with sulfonamides and sulfamate esters as the nitrogen source and iodosylbenzene (PhI{double bond, long}O) as the oxidant is reported herein. The reaction is operationally straight
Imido transfer from bis(imido)ruthenium(VI) porphyrins to hydrocarbons: Effect of imido substituents, C-H bond dissociation energies, and Ru VI/V reduction potentials
Leung, Sarana Ka-Yan,Tsui, Wai-Man,Huang, Jie-Sheng,Che, Chi-Ming,Liang, Jiang-Lin,Zhu, Nianyong
, p. 16629 - 16640 (2007/10/03)
[RuVI(TMP)(NSO2R)2] (SO2R = Ms, Ts, Bs, Cs, Ns; R = p-C6H4OMe, p-C6H 4Me, C6H5, p-C6H4-Cl, p-C6H4NO2, respectively) and [Ru VI(Por)(NTs)2] (Por = 2,6-Cl2TPP, F 20-TPP) were prepared by the reactions of [RuII(Por)(CO)] with Phl=NSO2R in CH2Cl2. These complexes exhibit reversible RuVI/V couple with E1/2 = -0.41 to -0.12 V vs Cp2Fe+/10 and undergo imido transfer reactions with styrenes, norbornene, cis-cyclooctene, indene, ethylbenzenes, cumene, 9,10-dihydroanthracene, xanthene, cyclohexene, toluene, and tetrahydrofuran to afford aziridines or amides in up to 85% yields. The second-order rate constants (k2) of the aziridination/amidation reactions at 298 K were determined to be (2.6 ± 0.1) × 10-5 to 14.4 ± 0.6 dm3 mol-1 s-1, which generally increase with increasing RuVI/V reduction potential of the imido complexes and decreasing C-H bond dissociation energy (BDE) of the hydrocarbons. A linear correlation was observed between log K (K is the k2 value divided by the number of reactive hydrogens) and BDE and between log k2 and E1/2(RuVI/V); the linearity in the former case supports a H-atom abstraction mechanism. The amidation by [RuVI(TMP)(NNs) 2] reverses the thermodynamic reactivity order cumene > ethylbenzene/toluene, with K(3° C-H)/K(2° C-H) = 0.2 and K(3° C-H)/K(1° C-H) = 0.8.
