392274-55-4Relevant academic research and scientific papers
Double Functionalization of Styrenes by Cu-Mediated Assisted Tandem Catalysis
Kawauchi, Daichi,Ueda, Hirofumi,Tokuyama, Hidetoshi
supporting information, p. 2056 - 2060 (2019/03/13)
The double functionalization of styrenes through Cu-mediated assisted tandem catalysis was developed. The reaction was initiated by Cu-catalyzed aziridination and the subsequent nucleophilic ring-opening, which was triggered by the addition of (NH4)2S2O8 as an oxidant of Cu-catalyst to form a variety of C–C and C–X bonds. The expansion to three contiguous catalytic cycles led to the synthesis of functionalized indolines by one-pot operation.
Synthesis of β-alkoxy-: N -protected phenethylamines via one-pot copper-catalyzed aziridination and ring opening
Saavedra-Olavarría, Jorge,Madrid-Rojas, Matías,Almodovar, Iriux,Hermosilla-Ibá?ez, Patricio,Pérez, Edwin G.
, p. 27919 - 27923 (2018/08/16)
A regioselective, copper-catalyzed, one-pot aminoalkoxylation of styrenes using primary and secondary alcohols and three different iminoiodanes as alkoxy and nitrogen sources respectively, is reported. The β-alkoxy-N-protected phenethylamines obtained were used to synthesise β-alkoxy-N-benzylphenethylamines which are interesting new compounds that could act as possible neuronal ligands.
Photo-induced aziridination of alkenes with N-sulfonyliminoiodinanes
Masakado, Sota,Kobayashi, Yusuke,Takemoto, Yoshiji
, p. 688 - 690 (2018/06/11)
Activation of N-sulfonyliminiodinanes was achieved by photo-irradiation at 375nm, which enabled the reaction with several alkenes to afford the corresponding aziridines. Mechanistic studies suggested that the reaction would proceed through a stepwise mech
Functionalization of Alkenes through Telescoped Continuous Flow Aziridination Processes
Hsueh, Nathanael,Clarkson, Guy J.,Shipman, Michael
supporting information, p. 4908 - 4911 (2016/10/18)
Alkenes can be efficiently aziridinated using highly soluble iminoiodane derivatives under continuous flow conditions. By combining the aziridine generation with nucleophilic ring opening reactions, a variety of products can be made without the need to ha
METAL PORPHYRIN CATALYZED OLEFIN AZIRIDINATION WITH SULFONYL AZIDES
-
Page/Page column 29; 40, (2009/12/27)
Cobalt(II) complex of P1 [Co(P1)], a new porphyrin that was designed on the basis of potential hydrogen bonding interactions in the metal-nitrene intermediate, is a highly active catalyst for olefin aziridination with azides. The [Co(P1)]- based system can be effectively employed for different combinations of aromatic olefins and arysulfonyl azides, synthesizing various sulfonylated aziridines in excellent yields. Besides its mild catalytic conditions, the Co-catalyzed aziridination process enjoys several attributes associated with the relatively low cost of cobalt and widely accessible arylsulfonyl azides. Furthermore, it generates stable dinitrogen as the only by-product.
A highly effective cobalt catalyst for olefin aziridination with azides: Hydrogen bonding guided catalyst design
Ruppel, Joshua V.,Jones, Jess E.,Huff, Chelsea A.,Kamble, Rajesh M.,Chen, Ying,Zhang, X. Peter
supporting information; experimental part, p. 1995 - 1998 (2009/04/10)
[Co(P1)], which was designed on the basis of potential hydrogen-bonding interactions in the metal-nitrene Intermediate, Is a highly active aziridination catalyst with azides. [Co(P1)] can effectively azlridlnate various aromatic olefins with arylsulfonyl azides under mild conditions, forming sulfonylated aziridines in excellent yields. The Co-based system enjoys several attributes associated with the relatively low cost of cobalt and the wide accessibility of arylsulfonyl azides. Furthermore, it generates stable dinitrogen as the only byproduct.
Catalytic asymmetric heterogeneous aziridination of styrene using CuHY: Effect of nitrene donor on enantioselectivity
Taylor, Sophia,Gullick, John,McMorn, Paul,Bethell, Donald,Page, Philip C. Bulman,Hancock, Frederick E.,King, Frank,Hutchings, Graham J.
, p. 1714 - 1723 (2007/10/03)
The copper-catalysed aziridination of styrene with copper-exchanged zeolite Y (CuHY) and copper(II) triflate (trifluoromethanesulfonate) (Cu(OTf)2) as catalysts is described in detail. Two nitrene donors, [N-(p-tolylsulfonyl)imino)]phenyliodinane (PhI=NTs) and [N-(p-nitrophenylsulfonyl)imino]phenyliodinane (PhI=NNs) are compared. Modification of the catalyst with bis(oxazolines) affords enantioselective catalysts and a range of chiral bis-(oxazolines) has been studied. The ratio of nitrene donor to styrene is shown to be an important factor controlling both the yield and ee of aziridine formed. The best results are obtained with PhI=NNs; ee, ≥ 90%, together with high yields (≥ 85%), can readily be achieved with this nitrene donor using acetonitrile as solvent. Addition of the nitrene donor over a period of time, rather than all at the start of the reaction, is shown to enhance the yield of the aziridine but the ee is significantly decreased for both the homogeneous and the heterogeneous catalysts. Experiments in which the breakdown products of the nitrene donor, iodobenzene and the corresponding sulfonamide, are added at the star of the reaction show that a complex interplay exists at the copper active site between the reactants, products, chiral modifier and the solvent. However, the heterogeneous catalyst, CuHY, is found to give enhanced enantioselection for a range of bis(oxazolines) compared to the homogeneous catalyst, and the effect is considered to be due to the confinement of the catalyst within the micropores of the zeolite.
