24962-83-2Relevant academic research and scientific papers
Aerobic Catalytic Features in Photoredox- and Copper-Catalyzed Iodolactonization Reactions
Ariyarathna, Jeewani Poornima,Wu, Fan,Colombo, Sara Katelyn,Hillary, Charleese Marisa,Li, Wei
, p. 6462 - 6466 (2018/10/15)
Mechanistic evaluations and comparison of two important aerobic catalytic oxidation processes, aerobic copper catalysis and photoredox catalysis, are performed. Interesting and distinct catalytic behaviors were observed for a common reaction of iodolacton
MnO2-promoted carboesterification of alkenes with anhydrides: A facile approach to γ-lactones
Wu, Lihuan,Zhang, Zhenming,Liao, Jianhua,Li, Jianxiao,Wu, Wanqing,Jiang, Huanfeng
supporting information, p. 2628 - 2631 (2016/02/18)
An efficient carboesterification of alkenes with anhydrides promoted by MnO2 has been developed to afford functionalized γ-lactones in good to excellent yields. This method shows a broad substrate scope and provides a valuable and convenient synthetic tool for constructing γ-lactones.
Flow Metal-Free Ar-C Bond Formation via Photogenerated Phenyl Cations
Bergami, Matteo,Protti, Stefano,Ravelli, Davide,Fagnoni, Maurizio
supporting information, p. 1164 - 1172 (2016/04/19)
A convenient photochemical flow protocol for the formation of aryl-carbon bonds via photogenerated phenyl cations has been developed. A wide range of phenylated products, including biaryls, allylarenes, 2-arylacetals and benzyl γ-lactones, was smoothly synthesized in satisfactory yields under metal-free conditions. The adoption of a flow reactor often allowed us to adopt higher concentrations of substrates and shorter irradiation times compared to those usually employed in batch systems.
Aryl imidazylates and aryl sulfates as electrophiles in metal-free ArSN1 reactions
Qrareya, Hisham,Protti, Stefano,Fagnoni, Maurizio
, p. 11527 - 11533 (2015/01/16)
Some oxygen-bonded substituents were investigated as leaving groups in photoinduced ArSN1 reactions. Irradiation of aryl imidazylates and of the corresponding imidazolium salts mainly caused homolysis of the ArO-S bond. However, previously unexplored trifluoroethoxy aryl sulfates were found to undergo efficient metal-free arylation. The sulfates were conveniently generated in situ by dissolving the corresponding imidazolium salts in basic 2,2,2-trifluoroethanol.
Metal-free arylations via photochemical activation of the Ar-OSO 2R bond in aryl nonaflates
Raviola, Carlotta,Canevari, Veronica,Protti, Stefano,Albini, Angelo,Fagnoni, Maurizio
, p. 2704 - 2708 (2013/10/08)
The photolysis of electron-rich aryl nonaflates (ArONfs) in protic media was investigated and heterolysis of the Ar-OS bond (from 3ArONf) took place. The reaction generated a triplet phenyl cation that added to π-bond nucleophiles. This metal-free arylation method was made further useful by adopting in situ preparation of ArONf from the corresponding phenol.
DIRECT ANTI-MARKOVNIKOV ADDITION OF ACIDS TO ALKENES
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Page/Page column 2; 14; 15, (2013/12/03)
A method of making an anti-Markovnikov addition product is carried out by reacting an acid with an alkene or alkyne in a dual catalyst reaction system to the exclusion of oxygen to produce said anti-Markovnikov addition product; the dual catalyst reaction system comprising a single electron oxidation catalyst in combination with a hydrogen atom donor catalyst. Compositions useful for carrying out such methods are also described.
Direct catalytic anti-markovnikov hydroetherification of alkenols
Hamilton, David S.,Nicewicz, David A.
supporting information, p. 18577 - 18580 (2013/01/15)
A direct intramolecular anti-Markovnikov hydroetherification reaction of alkenols is described. By employing catalytic quantities of commercially available 9-mesityl-10-methylacridinium perchlorate and 2-phenylmalononitrile as a redox-cycling source of a
Enantioselective synthesis of syn / anti -1,3-amino alcohols via proline-catalyzed sequential α-aminoxylation/α-amination and horner-wadsworth-emmons olefination of aldehydes
Jha, Vishwajeet,Kondekar, Nagendra B.,Kumar, Pradeep
supporting information; experimental part, p. 2762 - 2765 (2010/08/19)
(Figure presented) A novel and general method for asymmetric synthesis of both syn/anti-1,3-amino alcohols is described. The method uses proline-catalyzed sequential α-aminoxylation/ α-amination and Horner-Wadsworth-Emmons (HWE) olefination of aldehydes as the key step. By using this method, a short synthesis of a bioactive molecule, (R)-1-((S)-1-methylpyrrolidin-2-yl)-5- phenylpentan-2-ol, is also accomplished.
Benzyl (phenyl) γ- and δ-lactones via photoinduced tandem Ar-C, C-O bond formation
Protti, Stefano,Fagnoni, Maurizio,Albini, Angelo
, p. 10670 - 10671 (2007/10/03)
A convenient metal-free procedure for the preparation of benzyl (phenyl) γ- and δ-lactones is illustrated. This method is based on the photochemical generation of phenyl cations and their reaction with 3, 4, or 5-alkenoic acids. This leads to a phenyl- or benzyl-substituted lactone by tandem formation of an aryl-C and C-O bond. The intermediacy of a phenonium ion imparts a full regio- and stereoselectivity to the reaction. Copyright
Model studies towards the total synthesis of GKK1032s, novel antibiotic anti-tumor agents: Enantioselective synthesis of the alkyl aryl ether portion of GKK1032s
Asano, Moriteru,Inoue, Munenori,Katoh, Tadashi
, p. 2599 - 2602 (2007/10/03)
An enantioselective synthesis of an alkyl aryl ether portion of GKK1032s, novel antibiotic anti-tumor agents, was achieved via Mitsunobu reaction between a sterically congested indenol derivative and a p-substituted phenol derivative. The indenol derivati
