64935-37-1Relevant academic research and scientific papers
Silica gel-mediated self-aldol reactions of highly volatile aldehydes under organic solvent-free conditions without reflux condenser
Tanemura, Kiyoshi
supporting information, p. 1924 - 1928 (2019/06/24)
Silica gel-mediated self-aldol reactions were catalyzed by piperidine to give the corresponding α,β-conjugated aldehydes in good yields. The aldol reactions of 4-nitro-, 4-trifluoromethyl-, and 4-chlorobenzaldehydes with acetone afforded the corresponding aldol products. Highly volatile aldehydes and acetone could be employed even without a reflux condenser for these reactions. Silica gel could be recycled five times without any significant decrease of the yields of the products.
Nickel-Catalyzed α-Allylation of Aldehydes and Tandem Aldol Condensation/Allylation Reaction with Allylic Alcohols
Bernhard, Yann,Thomson, Brodie,Ferey, Vincent,Sauthier, Mathieu
supporting information, p. 7460 - 7464 (2017/06/13)
An additive-free nickel-catalyzed α-allylation of aldehydes with allyl alcohol is reported. The reaction is promoted by 1 mol % of in situ formed nickel complex in methanol, and water is the sole by-product of the reaction. The experimental conditions allow the conversion of various α-branched aldehydes and α,β-unsaturated aldehydes as nucleophiles. The same catalyst and reaction conditions enabled a tandem aldol condensation of aldehyde/α-allylation reaction.
Process for the catalytic production of unsaturated aldehydes
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Page/Page column 17; 18, (2016/02/05)
The invention concerns a process for the catalytic production of unsaturated aldehydes by reacting an olefin in the presence of carbon monoxide and hydrogen, a rhodium compound and organic phosphorus-containing ligands in an organic solvent as well as a co-catalyst formed from a weak organic acid and an organic amine.
Expanding the Scope of the Gold(I)-Catalyzed Rautenstrauch Rearrangement: Protic Additives
Bürki, Cédric,Whyte, Andrew,Arndt, Sebastian,Hashmi, A. Stephen K.,Lautens, Mark
supporting information, p. 5058 - 5061 (2016/10/14)
The synthesis of substituted 2-cyclopentenones using a commercially available gold(I) catalyst is described under flexible reaction conditions. During the course of our investigations, we discovered that using a proton source as an additive is required to obtain the desired substituted cyclopentenones in good yields.
Domino-Hydroformylation/Aldol Condensation Catalysis: Highly Selective Synthesis of α,β-Unsaturated Aldehydes from Olefins
Fang, Xianjie,Jackstell, Ralf,Franke, Robert,Beller, Matthias
supporting information, p. 13210 - 13216 (2016/02/19)
A general and highly chemo-, regio-, and stereoselective synthesis of α,β-unsaturated aldehydes by a domino hydroformylation/aldol condensation reaction has been developed. A variety of olefins and aromatic aldehydes were efficiently converted into various substituted α,β-unsaturated aldehydes in good to excellent yields in the presence of a rhodium phosphine/acid-base catalyst system. In view of the easy availability of the substrates, the high atom-efficiency, the excellent selectivity, and the mild conditions, this method is expected to complement current methodologies for the preparation of α,β-unsaturated aldehydes.
A selective solvent-free self-condensation of carbonyl compounds utilizing microwave irradiation
Sharma, Lalit Kumar,Kim, Kyung Bo,Elliott, Gregory I.
supporting information; experimental part, p. 1546 - 1549 (2011/07/31)
An environmentally benign microwave-assisted solvent-free self-condensation of carbonyl compounds was developed using catalytic amounts of triethylamine and lithium perchlorate. Changing the amount of lithium perchlorate helps in controlling the ratio of the single-condensation and double-condensation products. The effect of other additives and microwave activation was also investigated. The optimized conditions were then applied to various cyclic/acyclic ketones and aldehydes, with selectivity observed in many cases.
Synthesis of α-cyanocinnamaldehydes from acrylonitrile and benzaldehydes catalyzed by Pd(OAc)2/HPMoV/FeCl3/O 2 system
Maeda, Sayuki,Horikawa, Norihide,Obora, Yasushi,Ishii, Yasutaka
experimental part, p. 9558 - 9561 (2010/03/04)
(Chemical Equation Presented) A facile direct synthesis of (E)-α-cyanocinnamaldehydes from acrylonitrile and benzaldehydes is successfully achieved in a mixed solvent of EtOH/AcOH by Pd(OAc)2/ HPMoV/FeCl3/O2 catalyst syste
PROCESS FOR ALDOL CONDENSATION FOR PREPARATION OF α,β-UNSATURATED ALDEHYDE OR KETONE AND APPLICATION THEREOF IN SYNTHESIS OF SUBSTITUTED PYRROLE OR ARYLATION OF α,β-UNSATURATED ENAL
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Page/Page column 30-31, (2009/03/07)
A process for aldol condensation is provided. The process involves mixing of an α-unsubstituted aldehyde or ketone with another aldehyde or ketone under dry reaction conditions in the presence of an organocatalyst. The process for aldol condensation may be used for domino reactions, including the preparation of substituted pyrroles and the arylation of α,β-unsaturated enals.
Synthesis and sensorial properties of 2-alkylalk-2-enals and 3-(acetylthio)-2-alkyl alkanals
Robert, Fabien,Heritier, Julien,Quiquerez, Joelle,Simian, Herve,Blank, Imre
, p. 3525 - 3529 (2007/10/03)
Parallel synthesis was applied to prepare a series of 3-(acetylthio)-2-alkyl alkanals by Michael addition of thioacetic acid under alkaline conditions to α,β-unsaturated 2-alkyl-substituted aldehydes, which were obtained by aldol condensation of the corresponding primary aldehydes as starting materials. The target compounds were characterized in terms of GC, MS, and NMR data. The sensory properties of the odorants, such as odor quality and odor detection threshold value, were determined with a trained panel. Structure-activity relationships are discussed, suggesting that the 1,3-oxygen-sulfur functionality, required for the "olfactophore" of tropical/vegetable notes, can further be extended to the acetylthio derivatives.
Pyrrolidine-catalyzed homo-aidol condensation reactions of aldehydes
Ishikawa, Teruhiko,Uedo, Eiji,Okada, Siho,Saito, Seiki
, p. 450 - 452 (2007/10/03)
The first example of synthetically useful pyrrolidine-catalyzed homocoupling reaction of aliphatic aldehydes accelerated by benzoic acid is presented together with a plausible reaction mechanism. Thieme Stuttgart.
