881846-79-3Relevant articles and documents
Chan-Lam Amination of Secondary and Tertiary Benzylic Boronic Esters
Dennis, Francesca M.,Grayson, James D.,Partridge, Benjamin M.,Robertson, Craig C.
, p. 9883 - 9897 (2021/07/20)
We report a Chan-Lam coupling reaction of benzylic and allylic boronic esters with primary and secondary anilines to form valuable alkyl amine products. Both secondary and tertiary boronic esters can be used as coupling partners, with mono-alkylation of the aniline occurring selectively. This is a rare example of a transition-metal-mediated transformation of a tertiary alkylboron reagent. Initial investigation into the reaction mechanism suggests that transmetalation from B to Cu occurs through a single-electron, rather than a two-electron process.
Iron-catalyzed reductive coupling of nitroarenes with olefins: Intermediate of iron-nitroso complex
Song, Heng,Yang, Zhuoyi,Tung, Chen-Ho,Wang, Wenguang
, p. 276 - 281 (2019/12/24)
Using a single half-sandwich iron(II) compound, CpFe(1,2-Ph2PC6H4S)(NCMe) (Cp- = C5Me5-, 1) as a catalyst, reductive coupling of nitroarenes with olefins has been achieved by a well-defined iron(II)/(EtO)3SiH system. Through either inter- or intramolecular reductive coupling, various branched amines and indole derivatives have been directly synthesized in one-pot. Mechanistic studies showed that the catalysis is initiated by activation of nitroarenes by the iron(II) catalyst with silane, generating iron-nitrosoarene intermediate for the C-N bond coupling.
In Water Markovnikov Hydration and One-Pot Reductive Hydroamination of Terminal Alkynes under Ruthenium Nanoparticle Catalysis
Risi, Caterina,Cini, Elena,Petricci, Elena,Saponaro, Simone,Taddei, Maurizio
supporting information, p. 1000 - 1003 (2020/01/22)
In the presence of Shvo's catalyst [2,3,4,5-tetraphenyl-1,3-cyclopentadien-1-ol, ruthenium(II) complex], a small quantity of aniline and TGPS-750-M surfactant, terminal alkynes were hydrated under microwave (MW) dielectric heating in water as solvent with high conversion and good yield. The reaction gives the Markovnikov product exclusively, unlike that commonly observed with ruthenium complexes. Under the influence of MWs, Ru nanoparticles embedded in the nanomicelle environment were formed, acting as the effective hydration catalyst. Introducing sodium formate in the aqueous phase and using a stoichiometric amount of amines, the Ru nanoparticle nanomicelle catalyst gave the first example of one-pot single-step hydroamination of alkynes with the formation of the corresponding secondary amines. The reaction is characterized by low environmental impact as TGPS-750-M is required in low amount, and organic solvents employed only for product separation or catalyst recycling.