94533-51-4Relevant 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.
Radical fixation of functionalized carbon resources: α-sp 3C - H carbamoylation of tertiary amines with aryl isocyanates
Yoshimitsu, Takehiko,Matsuda, Kenichi,Nagaoka, Hiroto,Tsukamoto, Koji,Tanaka, Tetsuaki
, p. 5115 - 5118 (2008/03/28)
A new carbamoylation of tertiary amines is reported. This rare C - H transformation features the direct generation of α-aminoalkyl radicals from tertiary amines, followed by the addition of the resultant nucleophilic radicals to isocyanates, enabling unique access to N,N-dialkylated amino acid derivatives. The authors put forward a mechanistic proposal that is based on the isolation of borinamides produced by capturing nitrogen radical intermediates with Et3B. The present transformation provides a novel one-step process for producing mepivacaine, a clinically important local anesthetic, from readily available materials.