84395-76-6Relevant articles and documents
Dynamic Covalent Chemistry of Aldehyde Enamines: BiIII- and ScIII-Catalysis of Amine–Enamine Exchange
Zhang, Yang,Xie, Sheng,Yan, Mingdi,Ramstr?m, Olof
, p. 11908 - 11912 (2017/09/07)
The dynamic exchange of enamines from secondary amines and enolizable aldehydes has been demonstrated in organic solvents. The enamine exchange with amines was efficiently catalyzed by Bi(OTf)3 and Sc(OTf)3 (2 mol %) and the equilibria (60 mm) could be attained within hours at room temperature. The formed dynamic covalent systems displayed high stabilities in basic environment with 2 % by-product formation within one week after complete equilibration. This study expands the scope of dynamic C?N bonds from imine chemistry to enamines, enabling further dynamic methodologies in exploration of this important class of structures in systems chemistry.
Isolation of catalytic intermediates in hydroamination reactions: Insertion of internal alkynes into a zirconium-amido bond
Leitch, David C.,Turner, Courtney S.,Schafer, Laurel L.
supporting information; experimental part, p. 6382 - 6386 (2010/12/19)
Insert alkyne to continue: Reaction of a bis(ureate) zirconium dimethylamido complex with electron-rich alkynes leads to vinylamine insertion products (see scheme). The insertion of C=C unsaturated bonds into M=N bonds is proposed as a key step in lanthan
Anti-Markovnikov addition of both primary and secondary amines to terminal alkynes catalyzed by the TpRh(C2H4)2/PPH 3 system
Fukumoto, Yoshiya,Asai, Harumi,Shimizu, Masaki,Chatani, Naoto
, p. 13792 - 13793 (2008/04/04)
Terminal alkynes react with secondary amines in the presence of TpRh(C2H4)2/PPh3 (Tp = trispyrazolylborate) to give anti-Markovnikov E-enamines. Both Tp and PPh3 ligands are essential for the reaction. The reaction tolerates functional groups, such as ester, nitrile, and siloxy groups, on the terminal alkynes. Primary amines also add to terminal alkynes in anti-Markovnikov fashion, yielding the corresponding imines. The formation of a vinylidene-rhodium complex followed by the intermolecular nucleophilic attack by an amine nitrogen at the α-carbon atom of the vinylidene-metal intermediate may be involved in a key step in the catalytic reaction. Copyright