Atom-economical chemoselective synthesis of furocoumarins via cascade palladium catalyzed oxidative alkoxylation of 4-oxohydrocoumarins and alkenes

RSC Advances ◽  
2015 ◽  
Vol 5 (7) ◽  
pp. 4972-4975 ◽  
Author(s):  
Xian-chun Tan ◽  
Hai-yuan Zhao ◽  
Ying-ming Pan ◽  
Na Wu ◽  
Heng-shan Wang ◽  
...  
Keyword(s):  
Catalytic Amount ◽  
Efficient Procedure ◽  
Chemoselective Synthesis ◽  
Palladium Catalyzed ◽  
Oxidative Alkoxylation

A novel and efficient procedure for the synthesis of furo[3,2-c]coumarins from readily available 4-oxohydrocoumarins and alkenes in the presence of a catalytic amount of Pd(CF3COO)2 has been developed.

ChemInform Abstract: Atom-Economical Chemoselective Synthesis of Furocoumarins via Cascade Palladium Catalyzed Oxidative Alkoxylation of 4-Oxohydrocoumarins and Alkenes.

ChemInform ◽  
2015 ◽  
Vol 46 (24) ◽  
pp. no-no
Author(s):  
Xian-chun Tan ◽  
Hai-yuan Zhao ◽  
Ying-ming Pan ◽  
Na Wu ◽  
Heng-shan Wang ◽  
...  
Keyword(s):  
Chemoselective Synthesis ◽  
Palladium Catalyzed ◽  
Oxidative Alkoxylation

scholarly journals Palladium-catalyzed alkylation of unactivated olefins

2004 ◽  
Vol 76 (3) ◽  
pp. 671-678 ◽  
Author(s):  
Ross A. Widenhoefer
Keyword(s):  
Good Yield ◽  
Catalytic Amount ◽  
Outer Sphere ◽  
Deuterium Labeling ◽  
Carbon Nucleophiles ◽  
Keto Esters ◽  
Reactive Carbon ◽  
Aryl Ketones ◽  
Palladium Catalyzed ◽  
Hydride Elimination

The reaction of a 3-butenyl β-diketone with a catalytic amount of PdCl2(CH3CN)2 in dioxane at room temperature led to olefin hydroalkylation and formation of the corresponding 2-acylcyclohexanone in good yield as a single regioisomer. Deuterium-labeling experiments for the hydroalkylation of 7-octene-2,4-dione were in accord with a mechanism involving outer-sphere attack of the pendant enol on a palladium-complexed olefin to form a palladium cyclohexyl species, followed by palladium migration via iterative β-hydride elimination/addition and protonolysis from a palladium enolate complex. In comparison to a 3-butenyl β-diketone, reaction of a 4-pentenyl β-diketone with a catalytic amount of PdCl2(CH3CN)2 in the presence of CuCl2 led to oxidative alkylation and formation of the corresponding 2-acyl-3-methyl-2-cyclohexenone in good yield as a single isomer. Unactivated olefins tethered to less reactive carbon nucleophiles such as β-keto esters, α-aryl ketones, and even dialkyl ketones underwent palladium-catalyzed hydroalkylation in the presence of Me3SiCl or HCl to form the corresponding cyclohexanones in moderate-to-good yield with high regioselectivity.

ChemInform Abstract: Palladium-Catalyzed Chemoselective Synthesis of Indane-1,3-dione Derivatives via tert-Butyl Isocyanide Insertion.

ChemInform ◽  
2015 ◽  
Vol 46 (43) ◽  
pp. no-no
Author(s):  
Huaqing Duan ◽  
Zhong Chen ◽  
Li Han ◽  
Yulin Feng ◽  
Yongming Zhu ◽  
...  
Keyword(s):  
Tert Butyl ◽  
Chemoselective Synthesis ◽  
Palladium Catalyzed

scholarly journals Facile Deoxygenation of Hydroxylated Flavonoids by Palladium-Catalysed Reduction of its Triflate Derivatives

2005 ◽  
Vol 60 (7) ◽  
pp. 792-796 ◽  
Author(s):  
József Kövér ◽  
Sándor Antus
Keyword(s):  
Formic Acid ◽  
Functional Groups ◽  
Catalytic Amount ◽  
Palladium Acetate ◽  
Efficient Procedure ◽  
Related Compounds

An efficient procedure to deoxygenate hydroxy substituted flavonoids, isoflavonoids and related compounds via their trifluoromethanesulfonates is presented. Their reduction with formic acid in the presence of a catalytic amount of palladium acetate, triethylamine and 1,3-bis(diphenylphosphanyl) propane (dppp) in DMF results in their des-hydroxy derivatives without affecting other functional groups.

scholarly journals Synthesis and properties of tetrathiafulvalenes bearing 6-aryl-1,4-dithiafulvenes

2020 ◽  
Vol 16 ◽  
pp. 974-981 ◽  
Author(s):  
Aya Yoshimura ◽  
Hitoshi Kimura ◽  
Kohei Kagawa ◽  
Mayuka Yoshioka ◽  
Toshiki Itou ◽  
...  
Keyword(s):  
Catalytic Amount ◽  
Conjugated Molecules ◽  
Oxidation Potentials ◽  
Oxidation Step ◽  
Aryl Bromides ◽  
Palladium Catalyzed ◽  
Digital Simulations

Novel multistage redox tetrathiafulvalenes (TTFs) bearing 6-aryl-1,4-dithiafulvene moieties were synthesized by palladium-catalyzed direct C–H arylation. In the presence of a catalytic amount of Pd(OAc)2, P(t-Bu3)·HBF4, and an excess of Cs2CO3, the C–H arylation of TTF with several aryl bromides bearing 1,3-dithiol-2-ylidenes took place efficiently to produce the corresponding π-conjugated molecules. We also succeeded in the estimation of the oxidation potentials and number of electrons involved in each oxidation step of the obtained compounds by digital simulations.

A Convenient and Efficient Procedure for the Palladium-Catalyzed Cyanation of Aryl Halides Using Trimethylsilylcyanide.

ChemInform ◽  
2004 ◽  
Vol 35 (7) ◽  
Author(s):  
Mark Sundermeier ◽  
Sateesh Mutyala ◽  
Alexander Zapf ◽  
Anke Spannenberg ◽  
Matthias Beller
Keyword(s):  
Aryl Halides ◽  
Efficient Procedure ◽  
Palladium Catalyzed

scholarly journals An Efficient One-Pot Multicomponent Synthesis of 4-Aza-Podophyllotoxin Derivatives in Ionic Liquid

2013 ◽  
Vol 2013 ◽  
pp. 1-9 ◽  
Author(s):  
Hossein Naeimi ◽  
Zahra Rashid ◽  
Amir Hassan Zarnani ◽  
Ramin Ghahremanzadeh
Keyword(s):  
Ionic Liquid ◽  
Catalytic Amount ◽  
Multicomponent Synthesis ◽  
One Pot ◽  
Efficient Procedure ◽  
Mild Conditions ◽  
Three Component Reaction ◽  
Podophyllotoxin Derivatives

A simple, green, and efficient procedure for the synthesis of 4-aza-podophyllotoxin derivatives by using a one-pot three-component reaction of benzaldehydes, 1,3-cyclohexanediones, and anilinolactones in the presence of catalytic amount of alum in 1-butyl-3-methylimidazolium triflate as green media is described. This reaction proceeded under mild conditions with the use of an inexpensive and readily available catalyst, high to excellent yields, and simple workup procedure.

Palladium-Catalyzed C–P Cross-Coupling between (Het)aryl Halides and Secondary Phosphine Oxides

Synthesis ◽  
2019 ◽  
Vol 51 (11) ◽  
pp. 2379-2386 ◽  
Author(s):  
Gladis Zakirova ◽  
Dmitrii Mladentsev ◽  
Nataliya Borisova
Keyword(s):  
Electronic Properties ◽  
Heterocyclic Compounds ◽  
Cross Coupling ◽  
Secondary Phosphine ◽  
Phosphine Oxides ◽  
Tertiary Phosphine ◽  
Reaction Conditions ◽  
Efficient Procedure ◽  
Palladium Catalyzed ◽  
Tertiary Alkyl

An efficient procedure for C–P bond formation via the palladium-catalyzed [Pd(OAc)2/dppf/Cs2CO3] reaction between dichloroheterocycles and secondary phosphine oxides was developed. The steric and electronic properties of substituents were varied to establish the scope and limitations of the method developed. By applying these conditions, a variety of new heterocyclic compounds bearing two tertiary phosphine oxides were successfully synthesized in moderate to excellent yields. After adjustments to the reaction conditions [Pd(OAc)2/dippf/t-BuOK], cross-coupling of secondary phosphine oxides with bulky (secondary or tertiary alkyl) substituents on the phosphorus atom was achieved. Extension of the methodology to monohalohetarenes and monohaloarenes was successfully carried out; once again, the steric and electronic properties of the halides were varied widely. The desired reaction occurred in all cases studied, giving high to excellent yields of product regardless of the nature and positions of substituents.

“On water” palladium catalyzed diastereoselective boronic acid addition to structurally diverse cyclopropane nitriles

2020 ◽  
Vol 18 (43) ◽  
pp. 8886-8898
Author(s):  
Dwaipayan Das ◽  
Prasun Mukherjee ◽  
Asish R. Das
Keyword(s):  
Boronic Acid ◽  
Aqueous Media ◽  
Catalytic Amount ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Arylboronic Acids ◽  
Acid Addition ◽  
Brönsted Acid ◽  
Diastereoselective Addition ◽  
Palladium Catalyzed

An efficient palladium catalyzed diastereoselective addition of arylboronic acids to complex spirocyclopropyl dinitriles is developed in the presence of a catalytic amount of DBSA as a Brønsted acid surfactant in aqueous media.

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