104616-99-1Relevant academic research and scientific papers
Unprecedented Nucleophilic Additions of Highly Polar Organometallic Compounds to Imines and Nitriles Using Water as a Non-Innocent Reaction Medium
Dilauro, Giuseppe,Dell'Aera, Marzia,Vitale, Paola,Capriati, Vito,Perna, Filippo Maria
, p. 10200 - 10203 (2017)
In contrast to classic methods carried out under inert atmospheres with dry volatile organic solvents and often low temperatures, the addition of highly polar organometallic compounds to non-activated imines and nitriles proceeds quickly, efficiently, and chemoselectively with a broad range of substrates at room temperature and under air with water as the only reaction medium. Secondary amines and tertiary carbinamines are furnished in yields of up to and over 99 %. The significant solvent D/H isotope effect observed for the on-water nucleophilic additions of organolithium compounds to imines suggests that the on-water catalysis arises from proton transfer across the organic–water interface. The strong intermolecular hydrogen bonds between water molecules may play a key role in disfavoring protonolysis, which occurs extensively in other protic media such as methanol. This work lays the foundation for reshaping many fundamental s-block metal-mediated organic transformations in water.
Exploiting Deep Eutectic Solvents and Organolithium Reagent Partnerships: Chemoselective Ultrafast Addition to Imines and Quinolines Under Aerobic Ambient Temperature Conditions
Vidal, Cristian,García-álvarez, Joaquín,Hernán-Gómez, Alberto,Kennedy, Alan R.,Hevia, Eva
supporting information, p. 16145 - 16148 (2016/12/26)
Shattering the long-held dogma that organolithium chemistry needs to be performed under inert atmospheres in toxic organic solvents, chemoselective addition of organolithium reagents to non-activated imines and quinolines has been accomplished in green, b
Sterically Hindered Lithium Dialkylamides; A Novel Synthesis of Lithium Dialkylamides from N-t-Alkyl-N-benzylideneamines and the Isolation of Highly Hindered s-Alkyl-t-alkylamines
Cliffe, Ian A.,Crossley, Roger,Shepherd, Robin G.
, p. 1138 - 1140 (2007/10/02)
The convenient synthesis of lithium amides from imines 1 and organolithium reagents, and the isolation of the related highly hindered dialkylamines 3 are described.
