1555-31-3Relevant academic research and scientific papers
Visible-Light-Induced Metal-/Photocatalyst-Free C-H Bond Imidation of Arenes
Kuribara, Takahito,Nakajima, Masaya,Nemoto, Tetsuhiro
supporting information, p. 2235 - 2239 (2020/03/13)
In this study, a visible-light-induced intermolecular C-H bond imidation of arenes was achieved at ambient condition. By using simple phthalimide with (diacetoxyiodo)benzene and molecular iodine, direct metal-/photocatalyst-free C-N bond formation was achieved. The imidation protocol was designed by using time-dependent density functional theory calculations and experimentally demonstrated for 28 substrates with as high as 96% yield. Mechanistic studies indicated that radical-mediated aromatic substitution occurred via photolysis of N-iodophthalimide under visible-light irradiation.
Nickel-Catalyzed Electrochemical Phosphorylation of Aryl Bromides
Bai, Ya,Liu, Nian,Wang, Shutao,Wang, Siyu,Ning, Shulin,Shi, Lingling,Cui, Lili,Zhang, Zhuoqi,Xiang, Jinbao
supporting information, p. 6835 - 6838 (2019/09/30)
A nickel-catalyzed electrochemical cross-coupling reaction of aryl bromides with dialkyl phosphites, ethyl phenylphosphinate, and diphenylphosphine oxide has been developed. This reaction utilizes a simple undivided cell with inexpensive carbon electrodes to synthesize aryl phosphonates, aryl phosphinates, and arylphosphine oxides at room temperature. This protocol provides a mild and efficient route for the construction of C-P bond in moderate to high yields with broad substrate scope.
N-acyloxyphthalimides as nitrogen radical precursors in the visible light photocatalyzed room temperature C-H amination of arenes and heteroarenes
Allen, Laura J.,Cabrera, Pablo J.,Lee, Melissa,Sanford, Melanie S.
supporting information, p. 5607 - 5610 (2014/05/06)
This paper reports a room temperature visible light photocatalyzed method for the C-H amination of arenes and heteroarenes. A key enabling advance in this work is the design of N-acyloxyphthalimides as precursors to nitrogen-based radical intermediates for these transformations. A broad substrate scope is presented, including the selective meta-amination of pyridine derivatives. A radical aromatic substitution mechanism is proposed.
Sterically controlled, palladium-catalyzed intermolecular amination of arenes
Shrestha, Ruja,Mukherjee, Paramita,Tan, Yichen,Litman, Zachary C.,Hartwig, John F.
supporting information, p. 8480 - 8483 (2013/07/19)
We report the Pd-catalyzed amination of arenes to form N-aryl phthalimides with regioselectivity controlled predominantly by steric effects. Mono-, di-, and trisubstituted arenes lacking a directing group undergo amination reactions with moderate to high yields and high regioselectivities from sequential addition of PhI(OAc)2 as an oxidant in the presence of Pd(OAc) 2 as catalyst. This sterically derived selectivity contrasts that for analogous arene acetoxylation.
Crystal structures and triboluminescence based on trifluoromethyl and pentafluorosulfanyl substituted asymmetric N-phenyl imide compounds
Nakayama, Hikaru,Nishida, Jun-Ichi,Takada, Noriyuki,Sato, Hiroyasu,Yamashita, Yoshiro
experimental part, p. 671 - 676 (2012/06/15)
A series of asymmetric N-phenyl imides with trifluoromethyl and pentafluorosulfanyl substituents at the terminal phenyl position have been prepared. They are colorless both in solution and the solid state, and they show blue emission in the solid state. X-ray crystal structure analysis of trifluoromethyl and pentafluorosulfanyl substituted derivatives revealed highly ordered noncentrosymmetric molecular arrangements with large net-dipole moments related to the piezoelectric behavior. XRD measurements of the powders afforded intense sharp reflection peaks, indicating formation of the lamellar ordering. By grinding with a spatula, their solids showed vivid blue triboluminescence.
Multivariate regression with substituent shift increments. IV. 2-(4-X-phenyl)-1,3-dihydro-2H-isoindole-1,3-diones and 3-(4-X-phenyl)-3,4-dihydro-2H-1,3-benzoxazine-2,4-diones
Holik, Miroslav,Friedl, Zdenek,Waisser, Karel,Gregor, Jiri
, p. 1709 - 1726 (2007/10/03)
Two series of para disubstituted benzenes were studied: 2-(4-X-phenyl)-1,3-dihydro-2H-isoindole-1,3-diones (1) and 3-(4-X-phenyl)-3,4-dihydro-2H-1,3-benzoxazine-2,4-diones (2). Their 1H and 13C chemical shifts were correlated with substituent shift increments (SSI) aj and zj, respectively. For 13C chemical shifts, all four zj values, zj, zo, zm, and zp, were used to check the assignment and to find out possible variables for improvement of regression equations. Significant deviations from plain additivity were observed in the case of δH3 and δC3 chemical shifts. This can be explained by changes in diamagnetic anisotropy contribution induced by different twist of 4-substituent from the benzene plane caused by variable substituent in position 1.
