69849-46-3Relevant articles and documents
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
supporting information, p. 10200 - 10203 (2017/08/14)
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.
The chemistry of alkylstrontium halide analogues: Barbier-type alkylation of imines with alkyl halides
Miyoshi, Norikazu,Ikehara, Daitetsu,Kohno, Tadashi,Matsui, Aki,Wada, Makoto
, p. 760 - 761 (2007/10/03)
The chemistry of alkylstrontium halide analogues was examined. In the presence of metallic strontium, the Barbier-type alkylation of imines with alkyl iodides proceeded smoothly at room temperature under an argon atmosphere to afford the corresponding alk
The relationship between structure and tuberculostatic effect in the benzylamine group
Ruckdeschel,Stransky,Schoenenberger
, p. 374 - 381,375, 378, 380 (2007/10/06)
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