5216-84-2Relevant articles and documents
Convenient synthesis of a reactive ester homoenolate
DiMauro, Erin,Fry, Albert J.
, p. 7945 - 7949 (1999)
Reaction between methyl 3-phenyl-3-trimethylsilylpropionate (8) and catalytic quantities of tetrabutylammonium triphenyldifluorosilicate (TBAT) effects desilylation to the corresponding homoenolate, which can be trapped by a variety of electrophiles. Rear
Template Catalysis by Metal-Ligand Cooperation. C-C Bond Formation via Conjugate Addition of Non-activated Nitriles under Mild, Base-free Conditions Catalyzed by a Manganese Pincer Complex
Nerush, Alexander,Vogt, Matthias,Gellrich, Urs,Leitus, Gregory,Ben-David, Yehoshoa,Milstein, David
, p. 6985 - 6997 (2016/07/06)
The first example of a catalytic Michael addition reaction of non-activated aliphatic nitriles to α,β-unsaturated carbonyl compounds under mild, neutral conditions is reported. A new de-aromatized pyridine-based PNP pincer complex of the Earth-abundant, first-row transition metal manganese serves as the catalyst. The reaction tolerates a variety of nitriles and Michael acceptors with different steric features and acceptor strengths. Mechanistic investigations including temperature-dependent NMR spectroscopy and DFT calculations reveal that the cooperative activation of alkyl nitriles, which leads to the generation of metalated nitrile nucleophile species (α-cyano carbanion analogues), is a key step of the mechanism. The metal center is not directly involved in the catalytic bond formation but rather serves, cooperatively with the ligand, as a template for the substrate activation. This approach of "template catalysis" expands the scope of potential donors for conjugate addition reactions.
Hydroxy Chalcogenide-Promoted Morita-Baylis-Hillman Alkylation Reaction: Intermolecular Applications with Alkyl Halides as Electrophiles
Gradillas, Ana,Belmonte, Efres,Da Silva, Rondes Ferreira,Prez-Castells, Javier
, p. 1935 - 1941 (2015/10/05)
Hydroxysulfides acted as catalysts to promote the Morita-Baylis-Hillman alkylation reaction of cyclohexenones and dihydropyridinones. The procedure worked efficiently with a variety of halides as electrophiles. Side reactions were in competition with the
A novel method for the high-pressure-promoted, uncatalyzed aza-Michael reaction of nitrogen heterocycles with enones in water
Uddin, Md. Imam,Nakano, Keiji,Ichikawa, Yoshiyasu,Kotsuki, Hiyoshizo
experimental part, p. 1402 - 1406 (2009/04/06)
A new green chemical method for the aza-Michael reaction of nitrogen heterocycles with enones in water as a solvent without the use of any catalysts under high-pressure conditions is described. Georg Thieme Verlag Stuttgart.
