86926-25-2Relevant articles and documents
Dual-Role Catalysis by Thiobenzoic Acid in Cα-H Arylation under Photoirradiation
Kobayashi, Fumihisa,Fujita, Masashi,Ide, Takafumi,Ito, Yuta,Yamashita, Kenji,Egami, Hiromichi,Hamashima, Yoshitaka
, p. 82 - 87 (2021/01/11)
Thiobenzoic acid (TBA) can serve as a single-electron reducing agent under photoirradiation from a blue light-emitting diode, in the presence of appropriate electron acceptors, and the resulting sulfur-centered radical species undergoes hydrogen atom abstraction. This dual-role catalysis by TBA enables regioselectivie Cα-H arylation of benzylamines, benzyl alcohols, and ethers, as well as dihydroimidazoles, with cyano(hetero)arenes in good yield, without the need for a transition-metal photocatalyst and/or synthetically elaborated organic dyes.
Visible light mediated homo- and heterocoupling of benzyl alcohols and benzyl amines on polycrystalline cadmium sulfide
Mitkina, Tatiana,Stanglmair, Christoph,Setzer, Wolfgang,Gruber, Michael,Kisch, Horst,Koenig, Burkhard
supporting information; experimental part, p. 3556 - 3561 (2012/06/01)
The oxidative coupling of sp3 hybridized carbon atoms by photocatalysis is a valuable synthetic method as stoichiometric oxidation reagents can be avoided and dihydrogen is the only byproduct of the reaction. Cadmium sulfide, a readily available semiconductor, was used as a visible light heterogeneous photocatalyst for the oxidative coupling of benzyl alcohols and benzyl amines by irradiation with blue light. Depending on the structure of the starting material, good to excellent yields of homocoupling products were obtained as mixtures of diastereomers. Cross-coupling between benzyl alcohols and benzyl amines gave product mixtures, but was selective for the coupling of tetrahydroisoquinolines to nitromethane. The results demonstrate that CdS is a suitable visible light photocatalyst for oxidative bond formation under anaerobic conditions.
Titanocene-catalyzed coupling of aromatic amides in the presence of organosilanes: A novel route to vicinal diamines and a new class of amine-substituted oligomers
Rangareddy, Kesamreddy,Selvakumar, Kumaravel,Harrod, John F.
, p. 6843 - 6850 (2007/10/03)
The title reaction has been surveyed for a number of substrates with differing substitution patterns. With a few exceptions, the methodology provides a one-pot synthesis of the 1,2-diamines from widely available and inexpensive starting materials, and in high yields. In addition, the coupling of 1,4-and 1,3-bis-(N,N,N′,N′-tetraalkyl)arylenediamides is shown, under the same experimental conditions, to yield oligomers: R2NC(O)C 6H4CH(NR2)-[CH(NR2)C 6H4CH(NR2)]n-CH(NR 2)C6H4C(O)-NR2 (R = methyl and ethyl; n = 0 to ca. 5). The chemical structures of these unprecedented oligomers are determined by comparison of NMR and MS spectra to those of vicinal diamines, prepared from the analogous N,N-dialkylbenzamides. The origin of the limitation of oligomer chain length is probably due to a specific effect of the internal benzylic amine group, since the substrate 4-Me2NCH 2C6H4C(O)NMe2 was found to be uniquely unreactive compared to the other 4-substituted N,N-dialkylbenzamides investigated. N-Methylphthalimide was briefly studied as a monomer and analysis by MS showed that oligomers are formed. Attempts to fully characterize these polymers were unsuccessful.
