159659-19-5Relevant academic research and scientific papers
Transition-Metal-Free Stereospecific Oxidative Annulative Coupling of Indolines with Aziridines
Karjee, Pallab,Sarkar, Tanumay,Kar, Subhradeep,Punniyamurthy, Tharmalingam
, p. 8261 - 8270 (2020/07/25)
Tandem C-N bond formation for the oxidative annulation of indolines with aziridines is accomplished employing the combination of DDQ and NaOCl at ambient conditions. Optically active aziridine can be coupled with high enantiomeric purity (>99% ee). The substrate scope, stereocontrol with the enantioenriched substrate, and scale-up are the important practical advantages.
A bromo-capped diruthenium(i,i) N-heterocyclic carbene compound for in situ bromine generation with NBS: Catalytic olefin aziridination reactions
Sengupta, Gargi,Pandey, Pragati,De, Subhabrata,Ramapanicker, Ramesh,Bera, Jitendra K.
, p. 11917 - 11924 (2018/09/10)
A bromo-capped metal-metal bonded diruthenium(i,i) complex Ru2(CO)4(PIN)2Br2 (1) (PIN = 1-isopropyl-3-(5,7-dimethyl-1,8-naphthyrid-2-yl)imidazol-2-ylidene) generates bromine with N-bromosuccinimide (NBS) at room temperature. Cycloalkene and stilbene are readily brominated by stoichiometric reactions with 1 and NBS. An analysis of the dibrominated products suggests the formation of cyclic bromonium intermediates indicating in situ Br2 generation. Complex 2, an iodide analogue of 1, is also synthesized. The reaction of 2 with N-iodosuccinimide releases I2, which is confirmed by the starch-iodine test. The catalytic utility of 1 is examined for the bromination of phenol. Catalyst 1, in combination with NBS and base, exhibits regioselectivity towards monobrominated products. Furthermore, efficient olefin aziridination is demonstrated utilizing catalyst 1 in the presence of NBS, K2CO3 and TsNH2.
Stereospecific copper-catalyzed domino ring opening and sp3 C-H functionalization of activated aziridines with N-alkylanilines
Sengoden, Mani,Bhowmick, Abhisikta,Punniyamurthy, Tharmalingam
supporting information, p. 158 - 161 (2017/11/27)
Copper efficiently catalyzed nucleophilic ring opening, sp3 C-H functionalization, and C-N bond formation in the presence of tert-butyl hydroperoxide to afford functionalized imidazolidines starting from N-sulfonylaziridines and Nalkylanilines. The products were obtained in high optical purities (95 → 99% ee) with excellent functional group tolerance.
O-alkoxyphenyliminoiodanes: Highly efficient reagents for the catalytic aziridination of alkenes and the metal-free amination of organic substrates
Yoshimura, Akira,Nemykin, Victor N.,Zhdankin, Viktor V.
supporting information; experimental part, p. 10538 - 10541 (2011/11/12)
Efficient nitrene precursors: Highly reactive iminoiodane-based nitrene precursors were prepared from ortho-alkoxyiodobenzenes. Owing to the presence of the ortho-substituent on the phenyl ring, these new iminoiodanes have excellent solubility in organic
Copper(ii) complexes incorporating poly/perfluorinated alkoxyaluminate-type weakly coordinating anions: Syntheses, characterization and catalytic application in stereoselective olefin aziridination
Li, Yang,He, Jiayue,Khankhoje, Vineeta,Herdtweck, Eberhardt,Koehler, Klaus,Storcheva, Oksana,Cokoja, Mirza,Kuehn, Fritz E.
scheme or table, p. 5746 - 5754 (2011/08/02)
The synthesis and characterization of a series of cationic copper(ii) complexes of the type [Cu(NCR)6][Al(OC(CF3) 2R′)4]2 (R = CH3, Ph; R′ = CF3, Ph, PhCH3), incorpora
Highly efficient alkene epoxidation and aziridination catalyzed by iron(II) salt + 4,4′,4″-trichloro-2,2′:6′,2″-terpyridine/ 4,4″-dichloro-4′-O-PEG-OCH3-2,2′:6′,2″- terpyridine
Liu, Peng,Wong, Ella Lai-Ming,Yuen, Angella Wing-Hoi,Che, Chi-Ming
supporting information; experimental part, p. 3275 - 3278 (2009/05/27)
(Chemical Equation Presented) "Iron(II) salt + 4,4′,4″- trichloro-2,2′:6′,2″-terpyridine" is an effective catalyst for epoxidation and aziridination of alkenes and intramolecular amidation of sulfamate esters. The epoxidation of allylic-substituted cycloalkenes achieved excellent diastereoselectivities up to 90%. ESI-MS results supported the formation of iron-oxo and -imido intermediates. Derivitization of Cl3terpy to O-PEG-OCH3-Cl2terpy renders the terpyridine unit to be recyclable, and the "iron(II) salt + 4,4″-dichloro-4′-O-PEG-OCH3-2,2′:6′,2″- terpyridine" protocol can be reused without a significant loss of catalytic activity in the alkene epoxidation.
Investigations in the transition metal catalyzed aziridination of olefins, amination, and other insertion reactions with Bromamine-T as the source of nitrene
Chanda,Vyas,Bedekar
, p. 30 - 34 (2007/10/03)
Investigations into the transition metal catalyzed aziridination of olefins with Bromamine-T as a new source of nitrene is presented in this account. Comparison of Chloramine-T and Bromamine-T in this reaction indicates that the latter is superior as the source of nitrene. Systematic study with several transition metal based catalysts suggests that Cu-halides are the best catalysts. A first report of aziridination under microwave and ultrasound irradiation conditions is also presented. Copper-catalyzed aziridination of methyl cinnamate with Bromamine-T did not proceed at ambient temperature but was effected smoothly under ultrasound irradiation to furnish trans-aziridine selectively, while under microwave irradiation, a mixture of cis and trans isomers, was obtained. It has been demonstrated that aziridination of olefins proceeds smoothly with inexpensive bleaching powder. Preliminary results of Rh-catalyzed benzylic insertion reactions with Bromamine-T are included in this account.
Bromamine-T: A superior source of nitrene for aziridination of olefins
Vyas, Renu,Chanda,Bedekar, Ashutosh V.
, p. 4715 - 4716 (2007/10/03)
Bromamine-T as a superior source of nitrene compared to Chloramine-T in the Cu-catalyzed aziridination of olefins is reported in this communication.
