130786-09-3Relevant academic research and scientific papers
A Catalytic Peterson-like Synthesis of Alkenyl Nitriles
Lanari, Daniela,Alonzi, Matteo,Ferlin, Francesco,Santoro, Stefano,Vaccaro, Luigi
supporting information, p. 2680 - 2683 (2016/06/15)
A heterogeneous fluoride catalyst was found to enable the straightforward formation of alkenyl nitriles from the reaction of aldehydes and simple or substituted acetonitriles, in the presence of commercially available silazanes and in solvent-free conditions. The protocol afforded the products in good to excellent yields with selectivity values dependent on the nature of the substrates. It represents an alternative to classic approaches using stoichiometric strong bases, and the catalyst can be easily recovered and reused for consecutive cycles.
Aldol and Michael reactions of nitriles catalyzed by cyclopentadienyl- ruthenium enolate complexes
Murahashi, Shun-Ichi,Take, Kazuhiko,Naota, Takeshi,Takaya, Hikaru
, p. 1016 - 1018 (2007/10/03)
Novel cyclopentadienylruthenium enolate complexes, Ru+Cp(NCCRCO2Et) - (PPh3)2 (1) and Ru+Cp*(NCCRCO2Et) -(PPh3)2 (2) have been prepared by the re
Ruthenium-catalyzed aldol and Michael reactions of nitriles. Carbon-carbon bond formation by α-C-H activation of nitriles
Murahashi, Shun-Ichi,Naota, Takeshi,Taki, Hiroshi,Mizuno, Masahiko,Takaya, Hikaru,Komiya, Sanshiro,Mizuho, Yuji,Oyasato, Naohiko,Hiraoka, Makiko,Hirano, Masafumi,Fukuoka, Atsushi
, p. 12436 - 12451 (2007/10/03)
The ruthenium(II)-catalyzed reaction of nitriles with carbonyl compounds proceeds highly efficiently under neutral and mild conditions to give α,β-unsaturated nitriles. Under similar reaction conditions, nitriles react with olefins bearing electron-withdrawing groups to give the corresponding Michael adducts. The efficiency of the reaction is illustrated by the selective additions to α,β-unsaturated aldehydes and acetylenes bearing electron-withdrawing groups, which are difficult to perform using conventional bases. Chemoselective aldol and Michael reactions of nitriles can be performed in the presence of other active methylene compounds. Tandem Michael and Michael-aldol condensations of nitriles 30 can be performed with high diastereoselectivity. These reactions can be rationalized by assuming oxidative addition of ruthenium(0) to the α-C-H bond of nitriles and subsequent insertions to carbonyl compounds or olefins. As the key intermediates and active catalysts hydrido(N-bonded enolato)ruthenium(II) complexes, mer-RuH(NCCHCO2R)(NCCH2CO2R)(PPh3)3 (R = Me (41a), Et (41b), n-Bu (41c)) have been isolated upon treatment of RuH2(PPh3)4 (3) or RuH(C2H4)(PPh3)2(PPh2C6H4) (4) with alkyl cyanoacetates. Kinetic study of the catalytic aldol reaction of ethyl cyanoacetate with benzaldehyde indicates that the rate-determining step is the reaction of enolato complex 41 with aldehydes.
REACTIONS OF TITANIUM DERIVATIVES OF CERTAIN CH ACIDS WITH CARBONYL COMPOUNDS. II. ALDOL CONDENSATIONS WITH TITANIUM DERIVATIVES OF BENZYL CYANIDE, ISOPROPYL PHENYLACETATE, AND PHENYL BENZYL AND ETHYL BENZYL KETONES
Kasatkin, A. N.,Biktimirov, R. Kh.,Tolstikov, G. A.,Nikonenko, A. G.
, p. 1037 - 1045 (2007/10/02)
The titanium derivatives of benzyl cyanide, isopropyl phenylacetate, and phenyl benzyl and ethyl benzyl ketones, unlike the corresponding alkali-metal salts, react with aldehydes and ketones in THF at -78 to 20 deg C to form high yields of the products fr
Chain Reactions Induced by Cathodic Reduction
Shono, Tatsuya,Kise, Naoki,Masuda, Mitsuharu,Suzumoto, Takeshi
, p. 2527 - 2533 (2007/10/02)
Cathodic reduction of a system comprising carbon tetrachloride, chloroform, and an aldehyde led to an effective anionic chain reaction.The best current efficiency observed was about 1*104 percent .Such a chain reaction is an effective synthetic method for 1,1,1-trichloro-2-alkanols.The reaction system consisting of methyl trichloroacetate, methyl dichloroacetate, and an aldehyde and several other systems also exhibited a similar pattern of chain reaction.
