619-72-7Relevant articles and documents
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Vermillion,Hauser
, p. 1227 (1941)
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Syntheses and Optical Properties of Azo-Functionalized Ruthenium Alkynyl Complexes
Wei, Dilan,Kodikara, Mahesh S.,Morshedi, Mahbod,Moxey, Graeme J.,Wang, Huan,Wang, Genmiao,Quintana, Cristóbal,Zhang, Chi,Stranger, Rob,Cifuentes, Marie P.,Humphrey, Mark G.
, p. 621 - 628 (2016)
The syntheses of trans-[Ru(C≡C-1-C6H4-4-N=N-1-C6H4-4-C≡C-1-C6H4-4-NO2)Cl(L2)2] (L2=dppm (Ru1), dppe) (Ru2)), trans-[Ru(C≡C-1-C6H4-4-N=N-1-C6H4-4-(E)-CH=CH-1-C6H4-4-NO2)Cl(dppe)2] (Ru3), and trans-[Ru(C≡C-1-C6H4-4-(E)-CH=CH-1-C6H2-2,6-Et2-4-N=N-1-C6H4-4-NO2)Cl(dppe)2] (Ru4) are reported, together with those of precursor alkynes. Their electrochemical properties were assessed by cyclic voltammetry (CV), linear optical and quadratic nonlinear optical (NLO) properties assayed by UV/Vis-NIR spectroscopy and hyper-Rayleigh scattering studies at 1064 nm, respectively, and their linear optical properties in the formally RuIII state examined by UV/Vis-NIR spectroelectrochemistry. These data were compared to those of analogues with E-ene and yne linkages in place of the azo groups. Computational studies using time-dependent density functional theory were undertaken on model compounds (Ru2′–Ru4′) to rationalize the optical behaviour of the experimental complexes.
Nitrile Synthesis via Desulfonylative-Smiles Rearrangement
Abe, Masahiro,Nitta, Sayasa,Miura, Erina,Kimachi, Tetsutaro,Inamoto, Kiyofumi
, p. 4460 - 4467 (2022/03/15)
Herein, we designed a simple nitrile synthesis from N-[(2-nitrophenyl)sulfonyl]benzamides via base-promoted intramolecular nucleophilic aromatic substitution. The process features redox-neutral conditions as well as no requirement of toxic cyanide species and transition metals. Our process shows broad scope and various functional group compatibility, affording a variety of (hetero)aromatic nitriles in good to excellent yields.
Visible-Light-Promoted Metal-Free Synthesis of (Hetero)Aromatic Nitriles from C(sp3)?H Bonds**
Murugesan, Kathiravan,Donabauer, Karsten,K?nig, Burkhard
supporting information, p. 2439 - 2445 (2020/12/07)
The metal-free activation of C(sp3)?H bonds to value-added products is of paramount importance in organic synthesis. We report the use of the commercially available organic dye 2,4,6-triphenylpyrylium tetrafluoroborate (TPP) for the conversion of methylarenes to the corresponding aryl nitriles via a photocatalytic process. Applying this methodology, a variety of cyanobenzenes have been synthesized in good to excellent yield under metal- and cyanide-free conditions. We demonstrate the scope of the method with over 50 examples including late-stage functionalization of drug molecules (celecoxib) and complex structures such as l-menthol, amino acids, and cholesterol derivatives. Furthermore, the presented synthetic protocol is applicable for gram-scale reactions. In addition to methylarenes, selected examples for the cyanation of aldehydes, alcohols and oximes are demonstrated as well. Detailed mechanistic investigations have been carried out using time-resolved luminescence quenching studies, control experiments, and NMR spectroscopy as well as kinetic studies, all supporting the proposed catalytic cycle.
