33454-16-9Relevant articles and documents
Meta-metallation of N,N-dimethylaniline: Contrasting direct sodium-mediated zincation with indirect sodiation-dialkylzinc co-complexation
Armstrong, David R.,Balloch, Liam,Hevia, Eva,Kennedy, Alan R.,Mulvey, Robert E.,O'Hara, Charles T.,Robertson, Stuart D.
, p. 1234 - 1248 (2011)
Previously we reported that direct zincation of N,N-dimethylaniline by the mixed-metal zincate reagent 1 ((TMEDA)Na(TMP)(t-Bu)Zn(t-Bu)) surprisingly led to meta-metallation (zincation) of the aniline, as manifested in the crystalline complex 2 ((TMEDA)Na(
Scalable Synthesis of Acridinium Catalysts for Photoredox Deuterations
Fischer, Christian,Schneider, Lukas,Sparr, Christof,Zilate, Bouthayna
, p. 4359 - 4365 (2019/11/21)
The continuous development of photocatalytic methods incentivizes the design of organic catalysts to complement the frequently used and precious polypyridyl transition metal systems. Herein, a scalable synthesis of suitable acridinium dyes and their appli
Efficient and Selective N-Methylation of Nitroarenes under Mild Reaction Conditions
Pedrajas, Elena,Sorribes, Iván,Guillamón, Eva,Junge, Kathrin,Beller, Matthias,Llusar, Rosa
, p. 13205 - 13212 (2017/09/12)
Herein, we report a straightforward protocol for the preparation of N,N-dimethylated amines from readily available nitro starting materials using formic acid as a renewable C1 source and silanes as reducing agents. This tandem process is efficiently accomplished in the presence of a cubane-type Mo3PtS4 catalyst. For the preparation of the novel [Mo3Pt(PPh3)S4Cl3(dmen)3]+ (3+) (dmen: N,N′-dimethylethylenediamine) compound we have followed a [3+1] building block strategy starting from the trinuclear [Mo3S4Cl3(dmen)3]+ (1+) and Pt(PPh3)4 (2) complexes. The heterobimetallic 3+ cation preserves the main structural features of its 1+ cluster precursor. Interestingly, this catalytic protocol operates at room temperature with high chemoselectivity when the 3+ catalyst co-exists with its trinuclear 1+ precursor. N-heterocyclic arenes, double bonds, ketones, cyanides and ester functional groups are well retained after N-methylation of the corresponding functionalized nitroarenes. In addition, benzylic-type as well as aliphatic nitro compounds can also be methylated following this protocol.