61900-97-8Relevant articles and documents
Aminierende, reduktive Kupplung aromatischer Aldehyde mit Tris(dialkylamino)methylvanadium(IV) zu N,N,N',N'-Tetraalkyl-1,2-diarylaethylendiaminen
Imwinkelried, Rene,Seebach, Dieter
, p. 1496 - 1502 (1984)
In a novel type of reaction, certain aromatic aldehydes (benzaldehyde, p-methoxy-benzaldehyde, 1-naphthaldehyde, furan-2-carbaldehyde) and secondary amines are coupled to give N,N,N',N'-tetraalkyl-1,2-diarylethylenediamines 1-6.The reagents are tris(dialkylamino)methylvanadium(IV) compounds (cf.Eqn.2).These are generated in situ either from isolable chlorotris(dialkylamino)vanadium(IV) (Eqn. 3), or preferably, from an Et2O/pentane solution of VCl4 which is treated sequentially with 3 equiv. of lithium dialkylamide, 1 equiv. of MeLi, and equiv. of aromatic aldehyde, to give the products 1-6 in a one-pot preparation (Schem 2).The yields range from 14 to 54percent.The diastereomeric mixtures (meso- and (+/-)forms) obtained are separated by chromatography (Al2O3, petroleum ether/Et2O/Et3N), and the pure stereoisomers fully characterized.A mechanism of the reductive coupling induced by CH3V(NR2)3 is proposed (Scheme 1).
Oxidative and Redox-Neutral Approaches to Symmetrical Diamines and Diols by Single Electron Transfer/Hydrogen Atom Transfer Synergistic Catalysis
Fujita, Masashi,Kobayashi, Fumihisa,Ide, Takafumi,Egami, Hiromichi,Hamashima, Yoshitaka
supporting information, p. 7151 - 7155 (2020/12/01)
Homocoupling reactions of benzylamines and benzyl alcohols were examined under synergistic catalysis conditions with a photoredox catalyst and thiobenzoic acid as a hydrogen atom abstractor. When pivalaldehyde was used as an electron acceptor, oxidative dimerization proceeded selectively, whereas the use of benzaldehydes or iminium ions as electron acceptors resulted in redox-neutral coupling. These reactions afforded symmetrical 1,2-diamines and 1,2-diols in good yields.
Reductive coupling of aromatic N,N-acetals using zinc and chlorotrimethylsilane
Hatano, Bunpei,Tachikawa, Tomoharu,Mori, Tetsunori,Nagahashi, Keita,Kijima, Tatsuro
supporting information; experimental part, p. 3467 - 3469 (2011/07/08)
The reductive coupling of aromatic N,N-acetals and N,O-acetal activated by chlorotrimethylsilane proceeded smoothly in the presence of zinc to give the corresponding diamines in good yields.