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Relevant academic research and scientific papers

RhCl(PPh3)3/DPPF: A useful and efficient catalyst for cross-coupling reactions of activated alkenyl tosylates with arylboronic acids

A useful and effective rhodium catalyst system - [RhCl(PPh 3)3/DPPF] - for the Suzuki-Miyaura cross-coupling of activated alkenyl tosylates is described. The results not only represent the first examples of the rhodium-catalyzed Suzuki-Miyaura coupling of activated alkenyl tosylates with arylboronic acids under mild conditions, but also provide an efficient route for the synthesis of some natural product-like compounds, such as furan-2(5H)-one, coumarin, pyrone, and quinolin-2(1H)-one derivatives. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

Pd-catalyzed chemo-selective mono-arylations and bis-arylations of functionalized 4-chlorocoumarins with triarylbismuths as threefold arylating reagents

Cross-coupling reactions of differently substituted 4-chlorocoumarins were studied under palladium catalysis using triarylbismuths as threefold arylating reagents. The high reactivity of 4-chlorocoumarins was demonstrated delivering mono- and bis-arylation products in a chemo-selective manner. The reaction conditions employed are simple, robust and the threefold coupling reactivity of triarylbismuth reagents was witnessed with good to high yields in 2-4 h conditions. The utility of the methodology was explored in the synthesis of a few natural occurring neoflavones (3.27-3.30). In addition, the 4-arylcoumarin 3.1 product is a useful precursor for the preparation of (R)-tolterodine.

Coumarins from free ortho -hydroxy cinnamates by Heck-Matsuda arylations: A scalable total synthesis of (R)-tolterodine

Free ortho-hydroxy cinnamate ester derivatives are evaluated in the synthesis of structurally diverse 4-aryl-coumarins via a tandem Heck-Matsuda cyclization reaction. Free phenolic groups were considered incompatible with such a reaction, which usually provide the corresponding diazo dyes. A concise and scalable route employing a ligand-free, Pd-catalyzed Heck-Matsuda arylation under aerobic conditions for the preparation of (R)-Tolterodine in high overall yield and ee is also presented.

A convenient solid-phase synthesis of coumarins by TMSOTf-catalyzed intramolecular seleno-arylation of tethered alkenes

TMSOTf-catalyzed intramolecular seleno-arylation of tethered alkenes was performed using polystyrene-supported succinimidyl selenide as the selenium source. This catalytic process provides an efficient method for the regioselective synthesis of dihydrocou

Palladium-catalyzed synthesis of 4-arylcoumarins using triarylbismuth compounds as atom-Efficient multicoupling organometallic nucleophiles

Triarylbismuth compounds have been cross-coupled as atomefficient multicoupling organometallic nucleophiles with. 4bromo- and 4- (trifluoromethylsulfonyloxy)coumarins under palladium catalysis conditions. These reactions afforded an array of 4-arylcoumari

An efficient route to 4-substituted coumarins, 2(5H)-furanones, and pyrones via palladium-catalyzed couplings of alkenyl tosylates with organoindium reagents

Highly efficient palladium-catalyzed couplings of alkenyl tosylates with organoindium reagents under mild conditions are described, which give rise to 4-substituted coumarins, 2(5H)-furanones, and pyrones in good to excellent yields.

N-heterocyclic carbene derived Nickel-Pincer complexes: Efficient and applicable catalysts for Suzuki-Miyaura coupling reactions of aryl/alkenyl tosylates and mesylates

Catalytic activities of NHC-derived nickel-pincer complexes for the Suzuki-Miyaura coupling reactions of aryl/alkenyl to- sylates and mesylates are described. In the presence of a catalytic amount of nickelacycle 1a, a wide array of tosylates and mesylates reacted with several aryl- and alkenylboronic acids to afford the coupling products, generally in high yields. Fine tuning of the reaction conditions for each class of electrophiles was achieved only by choosing the appropriate reaction medium (DME for tosylates, dioxane for mesylates).