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
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.
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.
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.
, 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
